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1. Crystal structure of methyl 1,3-benzoxazole-2-carboxylate

Author: Alexandre Poirot, Nathalie Saffon-Merceron, Nadine Leygue, Eric Benoist, and Suzanne Fery-Forgues
Subjects: crystal structure, benzoxazole, herringbone arrangement, γ packing type, π–π interactions, strong c—h...n hydrogen bonds, Crystallography, QD901-999
Abstract: The title compound, C9H7NO3, crystallizes in the monoclinic (P21) space group. In the crystal, the almost planar molecules display a flattened herringbone arrangement. Stacking molecules are slipped in the lengthwise and widthwise directions and are linked by π–π interactions [d(Cg...Cg = 3.6640 (11) Å]. The structure is characterized by strong C—H...N and weak C—H...O hydrogen bonds, and further stabilized by C–O...π interactions.
Published: 2021
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2. Luminescent fac-[ReX(CO)3(phenyl-pyta)] (X = Cl, Br, I) complexes: influence of the halide ligand on the electronic properties in solution and in the solid state

Author: Alexandre Poirot, Corinne Vanucci-Bacqué, Béatrice Delavaux-Nicot, Nathalie Saffon-Merceron, Charles-Louis Serpentini, Nadine Leygue, Florence Bedos-Belval, Eric Benoist, Suzanne Fery-Forgues, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Université de Toulouse (UT), Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), IDeAS - Interfaces Dynamiques et Assemblages Stimulables (IDeAS), and Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT)
Subjects: Rhenium, Halogen, Crystal, Electrochemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Photoluminescence, DFT
Abstract: International audience; Tricarbonylrhenium(I) complexes that incorporate a chloride ligand are promising photoluminescent materials, but those incorporating a bromide or iodide ligand have received very little attention regarding their solid-state properties. In this work, three rhenium(I) complexes differing only by the nature of their halide ligand (X = Cl, Br, and I) were compared. They are based on a fac-[ReX(CO)3(N^N)] framework where the N^N bidentate ligand is a 3-(2-pyridyl)-1,2,4-triazole unit functionalized by an appended phenyl group. DFT calculations showed that the character of the lowest energy transitions progressively changes from Re → N^N ligand (MLCT) to X → N^N ligand (XLCT) when increasing the size of the halogen atom. Regarding the electrochemical behavior, the chloride and bromide complexes 1-Cl and 1-Br were similar, while the iodide complex 1-I exhibited a strikingly different electrochemical signature in oxidation. From a spectroscopic viewpoint, all three complexes emitted weak red–orange phosphorescence in dichloromethane solution. However, in the solid state, marked differences appeared. Not only was 1-Cl a good emitter of yellow light, but it had strong solid-state luminescence enhancement (SLE) properties. In comparison, 1-Br and 1-I were less emissive and they showed better mechanoresponsive luminescence (MRL) properties, probably related to a loose molecular arrangement in the crystal packing and to the opening of vibrational non-radiative deactivation pathways. This study highlights for the first time how the nature of the halide ligand in this type of complex allows fine tuning of the solid-state optical properties, for potential applications either in bio-imaging or in the field of MRL-active materials.
Published: 2022

3. Using a diphenyl-bi-(1,2,4-triazole) tricarbonylrhenium(<scp>i</scp>) complex with intramolecular π–π stacking interaction for efficient solid-state luminescence enhancement

Author: Alexandre Poirot, Corinne Vanucci-Bacqué, Béatrice Delavaux-Nicot, Clarisse Meslien, Nathalie Saffon-Merceron, Charles-Louis Serpentini, Florence Bedos-Belval, Eric Benoist, Suzanne Fery-Forgues, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Université de Toulouse (UT), Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), IDeAS - Interfaces Dynamiques et Assemblages Stimulables (IDeAS), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT), and ANR-22-CE29-0008,PANTHERA,Nanomatériaux à base de PhotoCORMs pour la thérapeutique antimicrobienne(2022)
Subjects: Inorganic Chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry
Abstract: International audience; Since intramolecular π–π stacking interactions can modify the geometry, crystal packing mode, or even the electronic properties of transition metal complexes, they are also likely to influence the solid-state luminescence properties. Following this concept, a new tricarbonylrhenium(I) complex (Re-BPTA) was designed, based on a simple symmetrical 5,5′-dimethyl-4,4′-diphenyl-3,3′-bi-(1,2,4-triazole) organic ligand. The complex was prepared in good yield using a three-step procedure. The crystallographic study revealed that both phenyl rings are located on the same side of the molecule, and twisted by 71° and 62°, respectively, with respect to the bi-(1,2,4-triazole) unit. They overlap significantly, although they are slipped parallel to each other to minimize the intramolecular interaction energy. The π–π stacking interaction was also revealed by 1H NMR spectroscopy, in good agreement with the results of theoretical calculations. In organic solutions, a peculiar electrochemical signature was observed compared to closely-related pyridyl-triazole (pyta)-based complexes. With regard to the optical properties, the stiffness of the Re-BPTA complex led to the stabilization of the 3MLCT state, and thus to an enhancement of the red phosphorescence emission compared to the more flexible pyta complexes. However, an increased sensitivity to quenching by oxygen appeared. In the microcrystalline phase, the Re-BPTA complex showed strong photoluminescence (PL) emission in the green-yellow wavelength range (λPL = 548 nm, ΦPL = 0.52, 〈τPL〉 = 713 ns), and thus a dramatic solid-state luminescence enhancement (SLE) effect. These attractive emission properties can be attributed to the fact that the molecule undergoes little distortion between the ground state and the triplet excited state, as well as to a favorable intermolecular arrangement that minimizes detrimental interactions in the crystal lattice. The aggregation-induced phosphorescence emission (AIPE) effect was clear, with a 7-fold increase in emission intensity at 546 nm, although the aggregates formed in aqueous medium were much less emissive than the native microcrystalline powder. In this work, the rigidity of the Re-BPTA complex is reinforced by the intramolecular π–π stacking interaction of the phenyl rings. This original concept provides a rhenium tricarbonyl compound with very good SLE properties, and could be used more widely to successfully develop this area of research
Published: 2023

4. ESIPT-Active cinnamoyl pyrones are bright solid-state emitters: Revisited theoretical approach and experimental study

Author: Emma Bremond, Martial Boggio-Pasqua, Nadine Leygue, Mokhtar Fodili, Pascal Hoffmann, Nathalie Saffon-Merceron, Rémi Métivier, Suzanne Fery-Forgues, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie et Physique Quantiques Laboratoire (LCPQ), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Fédération de recherche « Matière et interactions » (FeRMI), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS), Université Ziane Achour de Djelfa, Université de Toulouse (UT), Photophysique et Photochimie Supramoléculaires et Macromoléculaires (PPSM), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Ecole Normale Supérieure Paris-Saclay (ENS Paris Saclay), and ANR-17-CE07-0029,SUPERFON,Synthèse de nanocristaux organiques fluorescents en milieu fluide supercritique: une approche numérique et expérimentale complémentaire(2017)
Subjects: solid state luminescence enhancement (SLE), crystal structure, Process Chemistry and Technology, General Chemical Engineering, ESIPT, [CHIM]Chemical Sciences, photoluminescence, Aggregation induced emission (AIE), SF-TD-DFT, Aggregation induced emission (AIE) solid state luminescence enhancement (SLE) ESIPT photoluminescence crystal structure SF-TD-DFT
Abstract: International audience; Excited-state intramolecular proton transfer (ESIPT) is a photophysical process that may lead to superior emission properties. For a long time, cinnamoyl pyrone (CP) derivatives have been classified as non-ESIPT molecules. With the exception of those bearing a strong electron-donor substituent, they have been considered to have no interest from a spectroscopic point of view, because they are virtually not fluorescent in solution. Revisiting their photophysical behaviour in solution shows the complexity of the mechanisms involved. It appeared that CPs with no or weak electron-donor substituents indeed undergo ESIPT, but the facile access to a conical intersection subsequently induces non-radiative deactivation, hence the extinction of fluorescence in solution. When substituted by an electron-donating diethylamino group, the molecules deactivate through a radiative intramolecular charge transfer (ICT) state following an ESIPT process. In the solid state, the restricted access to conical intersection (RACI) makes most of the CP derivatives strongly fluorescent. Whatever the electron-donating strength of their substituent, most of these molecules become good emitters in the solid state, with emission ranging from turquoise blue to deep red. Although they need extensive purification, their one-step synthesis and spectacular aggregation-induced emission (AIE) properties make these molecules good candidates for applications in the field of AIE-probes and photoluminescent materials.
Published: 2023

5. Luminescent fac-[ReX(CO)

Author: Alexandre, Poirot, Corinne, Vanucci-Bacqué, Béatrice, Delavaux-Nicot, Nathalie, Saffon-Merceron, Charles-Louis, Serpentini, Nadine, Leygue, Florence, Bedos-Belval, Eric, Benoist, and Suzanne, Fery-Forgues
Abstract: Tricarbonylrhenium(I) complexes that incorporate a chloride ligand are promising photoluminescent materials, but those incorporating a bromide or iodide ligand have received very little attention regarding their solid-state properties. In this work, three rhenium(I) complexes differing only by the nature of their halide ligand (X = Cl, Br, and I) were compared. They are based on a fac-[ReX(CO)
Published: 2022

6. PhotoCORM-based nanomaterials for antimicrobial therapeutics

Author: Valentine GUILBAUD, Corinne VANUCCI-BACQUÉ, Florence BEDOS-BELVAL, Tan-Sothea OUK, Gautier M.-A. NDONG-NTOUTOUME, Vincent SOL, Éric BENOIST, and Suzanne FERY-FORGUES
Subjects: Oncology, Biophysics, Pharmacology (medical), Dermatology
Published: 2023

7. Recent Trends in the Design, Synthesis, Spectroscopic Behavior, and Applications of Benzazole-Based Molecules with Solid-State Luminescence Enhancement Properties

Author: Suzanne Fery-Forgues and Corinne Vanucci-Bacqué
Published: 2021

8. Crystal structure of methyl 1,3-benzoxazole-2-carboxylate

Author: Nathalie Saffon-Merceron, Eric Benoist, Suzanne Fery-Forgues, Alexandre Poirot, Nadine Leygue, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and Université de Toulouse (UT)
Subjects: crystal structure, Stacking, π–π interactions, strong c—h...n hydrogen bonds, Crystal structure, 010402 general chemistry, 01 natural sciences, Research Communications, Crystal, chemistry.chemical_compound, strong C—H⋯N hydrogen bonds, Group (periodic table), [CHIM]Chemical Sciences, General Materials Science, Crystallography, 010405 organic chemistry, Hydrogen bond, herringbone arrangement, General Chemistry, Benzoxazole, Condensed Matter Physics, γ packing type, 3. Good health, 0104 chemical sciences, benzoxazole, chemistry, QD901-999, π–π interactions, Monoclinic crystal system
Abstract: The herringbone structure of methyl 1,3-benzoxazole-2-carboxylate is characterized by strong C—H⋯N and weak C—H⋯O hydrogen bonds, and further stabilized by C—O⋯π and π–π interactions., The title compound, C9H7NO3, crystallizes in the monoclinic (P21) space group. In the crystal, the almost planar molecules display a flattened herringbone arrangement. Stacking molecules are slipped in the lengthwise and widthwise directions and are linked by π–π interactions [d(Cg⋯Cg = 3.6640 (11) Å]. The structure is characterized by strong C—H⋯N and weak C—H⋯O hydrogen bonds, and further stabilized by C–O⋯π interactions.
Published: 2021

9. Phenyl-pyta-tricarbonylrhenium(I) complexes: combining a simplified structure and steric hindrance to modulate the photoluminescence properties

Author: Nathalie Saffon-Merceron, Eric Benoist, Béatrice Delavaux-Nicot, Nadine Leygue, Fabienne Alary, Alexandre Poirot, Corinne Vanucci-Bacqué, Florence Bedos-Belval, Suzanne Fery-Forgues, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), Laboratoire de Chimie et Physique Quantiques (LCPQ), Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT), Laboratoire de Chimie et Physique Quantiques Laboratoire (LCPQ), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Fédération de recherche « Matière et interactions » (FeRMI), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), and Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Steric effects, Photoluminescence, Phosphorescence, Substituent, 02 engineering and technology, Benzoxazole, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, Fluorescence, DFT, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, Rhenium, chemistry, Electrochemical properties, Crystal, Phenyl group, [CHIM]Chemical Sciences, 0210 nano-technology, Luminescence, Mechanoresponsive luminescence
Abstract: International audience; Strongly luminescent tricarbonylrhenium(I) complexes are promising candidates in the field of optical materials. In this study, three new complexes bearing a 3-(2-pyridyl)-1,2,4-triazole (pyta) bidentate ligand with an appended phenyl group were obtained in very good yields owing to an optimized synthetic procedure. The first member of this series, i.e. complex 1, was compared with the previously studied complex RePBO to understand the influence of the fluorescent benzoxazole unit grafted on the phenyl ring. Then, to gauge the effect of steric hindrance on the luminescence properties, the phenyl group of complex 1 was substituted in the para position by a bulky tert-butyl group or an adamantyl moiety, affording complexes 2 and 3, respectively. The results of theoretical calculations indicated that these complexes were quite similar from an electronic point of view, as evidenced by the electrochemical study. In dichloromethane solution, under excitation in the UV range, all the complexes emitted weak phosphorescence in the red region. In the solid state, they could be excited in the blue region of the visible spectrum and they emitted strong yellow light. The photoluminescence quantum yield was markedly increased with raising the size of the substituent, passing from 0.42 for 1 to 0.59 for 3. The latter complex also exhibited clear waveguiding properties, unprecedented for rhenium complexes. From this point of view, these easy-synthesized and spectroscopically attractive complexes constitute a new generation of emitters for use in imaging applications and functional materials. However, the comparison with RePBO showed that the presence of the benzoxazole group leads to unsurpassed mechanoresponsive luminescence (MRL) properties, due to the involvement of a unique photophysical mechanism that takes place only in this type of complex.
Published: 2021

10. Microcrystals of an organic fluorescent dye grown in the presence of various PAMAM dendrimers: Control of the morphology and optical properties

Author: Franck Bertorelle, Fatima Al-Ali, and Suzanne Fery-Forgues
Subjects: Renewable energy sources, TJ807-830
Abstract: Microcrystals of a fluorescent dye, 4-n-octylamino-7-nitrobenzoxadiazole, were prepared by the reprecipitation method. Poly(amidoamine)dendrimers bearing anionic, cationic or neutral terminating groups were used as additives in the recrystallization medium. They directed the formation of thin plates or spindlelike microcrystals. The UV/vis absorption and emission properties were investigated on the microcrystal suspensions.
Published: 2004
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11. Use of oxazole-based chromophores as neat films in OLED structures: towards efficient deep-blue emitters

Author: Cédric Renaud, Houssein El Housseiny, Suzanne Fery-Forgues, Georges Zissis, David Buso, Marc Ternisien, LAboratoire PLasma et Conversion d'Energie (LAPLACE), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Lumière et Matière (LAPLACE-LM), and Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3)
Subjects: Materials science, Photoluminescence, 02 engineering and technology, Chromophore, Benzoxazole, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, Planarity testing, 010309 optics, chemistry.chemical_compound, chemistry, 0103 physical sciences, [SPI.OPTI]Engineering Sciences [physics]/Optics / Photonic, OLED, Molecule, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS, Diode, Oxazole
Abstract: Numerous oxazole-based fluorophores show efficient emission in the UV and deep blue spectral range in the solid state, making them interesting candidates for use as emissive layers in organic light-emitting diodes (OLEDs). Three ozazole derivatives, i.e. 2-(p-tert-butylphenyl)benzoxazole (Bzx), 2-phenyl-naphthoxazole (Nzx) and 2,2’-di(p-tert-butylphenyl)- 6,6’-bibenzoxazole (BBzx), were used in OLEDs with neat films configurations. These molecules differ by their planarity, steric hindrance and size of the π-conjugated system. No photoluminescence was observed with Bzx and Nzx. In contrast, the incorporation of the bis-chromophore BBzx within thin solid films led to efficient emission. The corresponding OLEDs displayed a deep blue emission at 430 nm arising from the BBzx layer, with CIE coordinate of (0.157, 0.044). These specific optical features were attributed to the twisted molecular structure of the bis-chromophore, leading to reduction of the aggregation induced fluorescence quenching. An EQE of 1.2% was achieved with a driving current of 24 A/m2. The results suggest that BBzx derivatives may be useful as efficient color saturation deep-blue emitters in OLEDs.
Published: 2021

12. The role of the synthetic chromophore of GFP in generating polymorphism-dependent on/off photoluminescence

Author: Nathalie Saffon-Merceron, Martial Boggio-Pasqua, Chantal Carayon, Christiane André-Barrès, Nadine Leygue, Suzanne Fery-Forgues, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), Photochimie théorique et computationnelle (LCPQ) (PTC), Laboratoire de Chimie et Physique Quantiques (LCPQ), Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT), Laboratoire de Chimie et Physique Quantiques Laboratoire (LCPQ), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Fédération de recherche « Matière et interactions » (FeRMI), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS), and ANR-17-CE07-0029,SUPERFON,Synthèse de nanocristaux organiques fluorescents en milieu fluide supercritique: une approche numérique et expérimentale complémentaire(2017)
Subjects: Photoluminescence, Materials science, Recrystallization (geology), Process Chemistry and Technology, General Chemical Engineering, 02 engineering and technology, Chromophore, Conical intersection, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Crystallography, Excited state, Molecule, Density functional theory, Singlet state, 0210 nano-technology
Abstract: Polymorphism, i.e. the ability of a solid material to exist in more than one crystal form, gives unique opportunity to study the correlation between the solid-state molecular arrangement and the photoluminescence properties, and allows optimizing the performances of materials with reduced synthesis effort. Compound 1, which results from the combination of 2-phenylbenzoxazole (PBO) and benzylideneimidazolinone (BDI), was known to be weakly fluorescent in solution and in the solid state. Time-dependent density functional theory (TD-DFT) and spin-flip TD-DFT calculations were first used to revisit the behaviour of the isolated molecule in solution. It was shown that the relaxation pathway in the lowest singlet excited state leads to a thermally-accessible conical intersection (CI), which favours non-radiative deactivation. Then, crystallizing molecule 1 under precise experimental conditions allowed four distinct polymorphs and one solvate to be obtained. Remarkably, forms 1a and 1b exhibited strong photoluminescence (PL), while polymorphs 1c-e were virtually not emissive. Recrystallization allowed passing reversibly from one crystalline species to another. Mechanical stimuli, exhibition to solvent vapours and heating were not very effective, but a non-trivial effect of PL enhancement upon freezing was observed for 1a and 1b. The non-emissive polymorphs were characterized by the presence of a centrosymmetric dimer structured by hydrogen bonds, in which paired molecules vibrate with the same mode and are in turn subjected to maximum deformation, according to DFT calculations. Based on the whole set of results, possible deactivation mechanisms were proposed to account for the opposite PL behaviour of the two types of crystalline species. It is shown that the emergence of polymorphism and of a rare on/off PL mechanism may be attributed to the presence of the BDI unit in the molecule.
Published: 2021

13. Efficient photorelease of carbon monoxide from a luminescent tricarbonyl rhenium(I) complex incorporating pyridyl-1,2,4-triazole and phosphine ligands

Author: Nathalie Saffon-Merceron, Eric Benoist, Suzanne Fery-Forgues, Ángel D. Hernández Mejías, Alexandre Poirot, Nadine Leygue, Meriem Rmili, Mariusz Wolff, University of Puerto Rico at Rio Piedras Campus (UPR-RP), Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut National des Sciences Appliquées et de Technologie [Tunis] (INSAT), Wirtschaftsuniversität Wien [Austria] (WU), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and Université de Toulouse (UT)
Subjects: Models, Molecular, Phosphines, 010402 general chemistry, Photochemistry, Ligands, 01 natural sciences, Article, Inorganic Chemistry, chemistry.chemical_compound, Coordination Complexes, Moiety, Molecule, [CHIM]Chemical Sciences, Density Functional Theory, Carbon Monoxide, Luminescent Agents, Molecular Structure, 010405 organic chemistry, Ligand, 1,2,4-Triazole, Triazoles, Photochemical Processes, 0104 chemical sciences, Rhenium, chemistry, Proton NMR, Phosphorescence, Phosphine, Carbon monoxide
Abstract: Precise control over the production of carbon monoxide (CO) is essential to exploit the therapeutic potential of this molecule. The development of photoactive CO-releasing molecules (PhotoCORMs) is therefore a promising route for future clinical applications. Herein, a tricarbonyl-rhenium(I) complex (1-TPP), which incorporates a phosphine moiety as ancilliary ligand for boosting the photochemical reactivity, and a pyridyltriazole bidentate ligand with appended 2-phenylbenzoxazole moiety for the purpose of photoluminescence, was synthesized and characterized from a chemical and crystallographic point of view. Upon irradiation in the near-UV range, complex 1-TPP underwent fast photoreaction, which was monitored through changes of the UV-vis absorption and phosphorescence spectra. The photoproducts (i.e. the dicarbonyl solvento complex 2 and one CO molecule) were identified using FTIR, 1H NMR and HRMS. The results were interpreted on the basis of DFT/TD-DFT calculations. The effective photochemical release of CO associated with clear optical variations (the emitted light passed from green to orange-red) could make 1-TPP the prototype of new photochemically-active agents, potentially useful for integration in photoCORM materials.
Published: 2021

14. Effect of substitution on the solid-state fluorescence properties of styrylbenzoxazole derivatives with terminal dicyanomethylene group

Author: Arnaud Erriguible, Suzanne Fery-Forgues, Emma Bremond, Thomas Jaouhari, Nathalie Saffon-Merceron, Nadine Leygue, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de la Matière Condensée de Bordeaux (ICMCB), Université de Bordeaux (UB)-Institut Polytechnique de Bordeaux-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), Institut de Mécanique et d'Ingénierie (I2M), Université de Bordeaux (UB)-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Arts et Métiers Sciences et Technologies, HESAM Université (HESAM)-HESAM Université (HESAM), ANR 'Superfon', ANR-17-CE07-0029,SUPERFON,Synthèse de nanocristaux organiques fluorescents en milieu fluide supercritique: une approche numérique et expérimentale complémentaire(2017), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT), and HESAM Université - Communauté d'universités et d'établissements Hautes écoles Sorbonne Arts et métiers université (HESAM)-HESAM Université - Communauté d'universités et d'établissements Hautes écoles Sorbonne Arts et métiers université (HESAM)
Subjects: Photoluminescence, General Chemical Engineering, General Physics and Astronomy, Nanoparticle, Benzoxazole, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Crystal, Chemistry, Intermolecular force, Solid state luminescence enhancement (SLE), General Chemistry, Aggregation induced emission (AIE), [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, Fluorescence, 3. Good health, 0104 chemical sciences, Amorphous solid, Crystallography, Microcrystalline, 0210 nano-technology, Luminescence
Abstract: International audience; Three styrylbenzoxazole derivatives with terminal dicyanomethylene group were studied in order to understand how minor modifications brought to the benzoxazole ring influence the photoluminescence (PL) properties. The three compounds, in which several molecular motions are allowed, were weakly fluorescent in organic solution. Remarkably, the unsubstituted (1) and methoxy (2) derivatives showed clear solid-state luminescence enhancement (SLE). Distinct emission characteristics were attributed to the formation of amorphous and crystalline particles owing to scanning electron microscopy. These two compounds were also strongly luminescent as microcrystalline powders. Compound 1 that crystallized in herringbone configuration was a better emitter than the methoxy derivative 2, in which intermolecular interactions are more numerous, according to X-ray diffraction analysis. In contrast, compound 3 was virtually not emissive, confirming that in this series of dyes the presence of the hydroxy group is detrimental to PL emission, as rarely observed among SLE-active fluorophores.
Published: 2021

15. Mechanical Modulation of the Solid‐State Luminescence of Tricarbonyl Rhenium(I) Complexes through the Interplay between Two Triplet Excited States

Author: Suzanne Fery-Forgues, Clémence Allain, Eric Benoist, Mariusz Wolff, Jinhui Wang, Alexandre Poirot, Rémi Métivier, Béatrice Delavaux-Nicot, Jan Patrick Calupitan, Maria Jaworska, Photophysique et Photochimie Supramoléculaires et Macromoléculaires (PPSM), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Ecole Normale Supérieure Paris-Saclay (ENS Paris Saclay), Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Ningbo University (NBU), State Key Laboratory of Chemical Oncogenomics, Tsinghua University, Laboratoire de chimie de coordination (LCC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Universität Wien, University of Silesia in Katowice, Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), European Research Council (ERC StG-715757 MECHANO-FLUO), and Chinese Scholarship Council
Subjects: Photoluminescence, Luminescence, 010405 organic chemistry, Organic Chemistry, chemistry.chemical_element, Mechanochromism, General Chemistry, Rhenium, 010402 general chemistry, Photochemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, Amorphous solid, Density functional calculations, Microcrystalline, chemistry, Molecular vibration, Excited state, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Fourier transform infrared spectroscopy
Abstract: International audience; Mechanoresponsive luminescence (MRL) materials promise smart devices for sensing, optoelectronics and security. We present here the first report on the MRL activity of two ReI complexes, opening up new opportunities for applications in these fields. Both complexes exhibit marked solid‐state luminescence enhancement (SLE). Furthermore, the pristine microcrystalline powders emit in the yellow‐green region, and grinding led to an amorphous phase with concomitant emission redshift and shrinking of the photoluminescence (PL) quantum yields and lifetimes. Quantum chemical calculations revealed the existence of two low‐lying triplet excited states with very similar energy levels, that is, 3IL and 3MLCT, having, respectively, almost pure intraligand (IL) and metal‐to‐ligand charge‐transfer (MLCT) character. Transition between these states could be promoted by rotation around the pyridyltriazole−phenylbenzoxazole bond. In the microcrystals, in which rotations are hindered, the 3IL state induces the prominent PL emission at short wavelengths. Upon grinding, rotation is facilitated and the transition to the 3MLCT state results in a larger proportion of long‐wavelength PL. FTIR and variable‐temperature PL spectroscopy showed that the opening of the vibrational modes favours non‐radiative deactivation of the triplet states in the amorphous phase. In solution, PL only arises from the 3MLCT state. The same mechanism accounts for the spectroscopic differences observed when passing from crystals to amorphous powders, and then to solutions, thereby clarifying the link between SLE and MRL for these complexes.
Published: 2021

16. 2-phenylbenzoxazole derivatives as solid-state fluorescence emitters: Influence of steric hindrance and hydrogen bonding on the optical properties

Author: Nathalie Saffon-Merceron, Nadine Leygue, Emma Bremond, Suzanne Fery-Forgues, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), and Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)
Subjects: chemistry.chemical_classification, Steric effects, Hydrogen bond, Substituent, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, Analytical Chemistry, chemistry.chemical_compound, Crystallinity, chemistry, Polymer chemistry, Molecule, Phenyl group, [CHIM]Chemical Sciences, 0210 nano-technology, Instrumentation, Spectroscopy, Alkyl, ComputingMilieux_MISCELLANEOUS, Methyl group
Abstract: Six new 2-phenylbenzoxazole (PBO) derivatives, bearing either a methoxy or hydroxy group at position 5, were prepared via an efficient one-step synthesis that allowed both analogues to be obtained in equal proportions. These PBO derivatives also differed by the presence or absence of an alkyl substituent at the para-position of the phenyl group. In organic solutions, all six compounds were strongly fluorescent in the near-UV range. In the solid state, the 5-methoxy derivatives emitted bright light, ranging from violet to deep blue according to the substitution of the phenyl group. The presence of a bulky tert-butyl group indeed resulted in the separation of molecules, but also led to a deviation from molecular planarity. Remarkably, the introduction of a methyl group had a far more beneficial effect on the optical properties. With regard to the hydroxy derivatives, none of them was photoluminescent, probably due to strong intermolecular hydrogen bonding in the crystals. The 50:50 mixtures of methoxy and hydroxy analogues showed acceptable emission properties in the solid state. The substitution pattern also influenced the crystal habit of the pure compounds and the crystallinity of the mixtures. These cheap molecules could be adapted to suit a variety of applications in the field of photoluminescent materials.
Published: 2020

17. Process intensification for the synthesis of ultra-small organic nanoparticles with supercritical CO2 in a microfluidic system

Author: Thomas Jaouhari, Samuel Marre, Suzanne Fery-Forgues, Cyril Aymonier, Fan Zhang, Arnaud Erriguible, Thierry Tassaing, Institut de Chimie de la Matière Condensée de Bordeaux (ICMCB), Université de Bordeaux (UB)-Institut Polytechnique de Bordeaux-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Mécanique et d'Ingénierie (I2M), Université de Bordeaux (UB)-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Arts et Métiers Sciences et Technologies, HESAM Université (HESAM)-HESAM Université (HESAM), We acknowledge the French National Research Agency for its support (ANR-17-CE07-0029 - SUPERFON), the University of Bordeaux for the Ph.D. funding of the author Fan Zhang, the MCIA (Mésocentre de Calcul Intensif Aquitaine) and GENCI (DARI project number A0062A10815) for the HPC resources., ANR-17-CE07-0029,SUPERFON,Synthèse de nanocristaux organiques fluorescents en milieu fluide supercritique: une approche numérique et expérimentale complémentaire(2017), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and HESAM Université - Communauté d'universités et d'établissements Hautes écoles Sorbonne Arts et métiers université (HESAM)-HESAM Université - Communauté d'universités et d'établissements Hautes écoles Sorbonne Arts et métiers université (HESAM)
Subjects: Materials science, General Chemical Engineering, Microfluidics, Population balance equation, Nanoparticle, 02 engineering and technology, Numerical simulation, 010402 general chemistry, 01 natural sciences, Industrial and Manufacturing Engineering, chemistry.chemical_compound, Supercritical fluid, Environmental Chemistry, Solubility, Nanoparticle synthesis, Supercritical carbon dioxide, General Chemistry, Tetraphenylethylene, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, chemistry, Chemical engineering, Microfluidic, Mixing intensification, Microreactor, 0210 nano-technology
Abstract: International audience; Submicronization of organic compounds is a challenging requirement for applications in the imaging and pharmaceutical fields. A new Supercritical AntiSolvent process with microreactor (µSAS) was developed for nanoparticle (NP) synthesis. Tetrahydrofuran (THF) was used to solubilize a model organic molecule, tetraphenylethylene, and supercritical carbon dioxide (sc-CO2) was used as antisolvent. The solubility of TPE in the THF/CO2 system was first measured by in situ experiments. Then, NPs of TPE were prepared in various experimental conditions and characterized by transmission electron microscopy (TEM). Chosen experimental conditions led to NPs with a mean size of 9 ± 3 nm. Experimental µSAS results were compared with size distributions obtained by simulation, to obtain surface tension values, which are difficult to access by experiment alone. Simulations coupling Computational Fluid Dynamics (CFD) and Population Balance Equation (PBE) were performed under turbulent conditions in the high pressure microreactors. This coupled experimental and theoretical approach allowed a deep understanding of the µSAS process and underlined the superior value of this technique for the preparation of NPs.
Published: 2020

18. Investigating nucleation and growth phenomena in microfluidic supercritical antisolvent process by coupling in situ fluorescence spectroscopy and direct numerical simulation

Author: Thierry Tassaing, Thomas Jaouhari, Samuel Marre, Cyril Aymonier, Suzanne Fery-Forgues, Arnaud Erriguible, Institut de Chimie de la Matière Condensée de Bordeaux (ICMCB), Université de Bordeaux (UB)-Institut Polytechnique de Bordeaux-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Institut de Mécanique et d'Ingénierie (I2M), Université de Bordeaux (UB)-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Arts et Métiers Sciences et Technologies, HESAM Université - Communauté d'universités et d'établissements Hautes écoles Sorbonne Arts et métiers université (HESAM)-HESAM Université - Communauté d'universités et d'établissements Hautes écoles Sorbonne Arts et métiers université (HESAM), We acknowledge the French National Research Agency for its support (ANR-17-CE07-0029 - SUPERFON), and the MCIA (Mésocentre de Calcul Intensif Aquitaine) and GENCI (DARI project number A0062A10815) for their HPC resources., ANR-17-CE07-0029,SUPERFON,Synthèse de nanocristaux organiques fluorescents en milieu fluide supercritique: une approche numérique et expérimentale complémentaire(2017), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and HESAM Université (HESAM)-HESAM Université (HESAM)
Subjects: Work (thermodynamics), Materials science, General Chemical Engineering, Direct numerical simulation, Mixing (process engineering), Nucleation, Precipitation, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Industrial and Manufacturing Engineering, Fluorescence spectroscopy, Mixing, Supercritical fluids, Supersaturation, Applied Mathematics, [CHIM.MATE]Chemical Sciences/Material chemistry, General Chemistry, 021001 nanoscience & nanotechnology, Supercritical fluid, 0104 chemical sciences, Microfluidic, Chemical physics, Particle, CFD, 0210 nano-technology
Abstract: International audience; High-pressure microfluidic systems exhibit favorable capacity to enhance mixing quality compared to conventional macroscale liquid systems. These mixing conditions are very interesting for the preparation of fluorescent organic nanoparticles by supercritical antisolvent process. In this work, fundamental mechanisms of microfluidic supercritical antisolvent process (µSAS) including thermodynamics, hydrodynamics, nucleation/growth phenomena, are investigated using a coupled experimental/simulation approach. Specifically, we determined experimentally the particle precipitation field in a CO2 / solvent medium using a fluorescent organic dye molecule which presents an enhancement of fluorescence intensity in its aggregated state (AIE effect). The results of the direct numerical simulation considering all the physical phenomena are compared with the experimental data for validation and deep understanding of the mechanisms. It is shown that despite ultra-short mixing time, the supersaturation field showed some fluctuation leading to variation of the nucleation times.
Published: 2022

19. Synthetic talc as a new platform for producing fluorescent clay polyurethane nanocomposites

Author: Mathilde Poirier, Guilherme Dias, Manoela Prado, Sandra Einloft, François Martin, Christophe Le Roux, Rosane Angélica Ligabue, Suzanne Fery-Forgues, Faculdade de Química (FAQUI), Pontifícia Universidade Católica do Rio Grande do Sul [Porto Alegre] (PUCRS), Institut de Chimie Moléculaire de l'Université de Bourgogne [Dijon] (ICMUB), Centre National de la Recherche Scientifique (CNRS)-Université de Bourgogne (UB)-Institut de Chimie du CNRS (INC), Géosciences Environnement Toulouse (GET), Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Observatoire Midi-Pyrénées (OMP), Météo France-Centre National d'Études Spatiales [Toulouse] (CNES)-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Météo France-Centre National d'Études Spatiales [Toulouse] (CNES)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chemistry.chemical_classification, Filler (packaging), Nanocomposite, Molar mass, Materials science, Polymer nanocomposite, Geology, 02 engineering and technology, Polymer, 010402 general chemistry, 021001 nanoscience & nanotechnology, Talc, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Chemical engineering, chemistry, Geochemistry and Petrology, medicine, [CHIM]Chemical Sciences, Fourier transform infrared spectroscopy, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS, Polyurethane, medicine.drug
Abstract: As a non-swelling clay, talc generally interacts very weakly with organic molecules. However, two new nanometric synthetic talcs that incorporate berberine chloride were successfully used as fluorescent fillers in clay polyurethane nanocomposites obtained by the blending method. A micrometric natural talc filler was also used for comparison. The clay polymer nanocomposites (CPN) were characterized by FTIR, molar mass analysis and XRD. All talc fillers were well dispersed into the polyurethane matrix even at high filler content of 5 wt%, as supported by TEM and SEM analyses. Morphological changes were confirmed by AFM. The optical properties of the fluorescent talcs, dye-doped polymer and CPN were compared. While the dye-doped polymer suffered from conventional fluorescence quenching due to dye aggregation, the emission quantum yield of the CPN was increased with increasing the filler content. The best emission efficiency was observed for the CPN that contains the smallest talc-berberine hybrid particles. The use of fluorescent synthetic talc resulted in materials with good thermal and mechanical properties, and can be considered as a new method to produce fluorescent CPN in view of multiple applications.
Published: 2018

20. The unsuspected influence of the pyridyl-triazole ligand isomerism upon the electronic properties of tricarbonyl rhenium complexes: an experimental and theoretical insight

Author: Suzanne Fery-Forgues, Jinhui Wang, Mariusz Wolff, Rémi Métivier, Béatrice Delavaux-Nicot, Eric Benoist, Sonia Mallet-Ladeira, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut of Physics, University of Silesia, University of Silesia in Katowice, Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires (PPSM), and École normale supérieure - Cachan (ENS Cachan)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 010405 organic chemistry, Band gap, Ligand, Triazole, chemistry.chemical_element, Rhenium, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Inorganic Chemistry, Ligand isomerism, Crystallography, chemistry.chemical_compound, chemistry, Structural isomer, Moiety, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Phosphorescence
Abstract: International audience; Two isomeric tricarbonyl rhenium(i) complexes, ReL1 and ReL2, that possess a 2-pyridyl-1,2,n-triazole (pyta) ligand (n = 4 and 3, respectively) connected to a 2-phenylbenzoxazole (PBO) moiety, were synthesized in good yields. The X-ray structures showed that in ReL1 the PBO moiety and the pyta ligand almost form a right angle hindering electron delocalization, while in ReL2 their nearly planar arrangement favors the electron delocalization in the whole organic ligand. Therefore, the nature of the ligand significantly influences the electron distribution in the two complexes, as indicated by the results of TD-DFT calculations. An electrochemical study highlighted that, by comparison with ReL2, the smaller HOMO–LUMO energy gap of ReL1 is in line with its lower first reduction potential. From a spectroscopic viewpoint, both complexes emitted phosphorescence in organic solvents, with distinct color and intensity. They also emitted in the solid state, but only ReL1 showed significant aggregation-induced phosphorescence emission (AIPE). This complete study sheds light on the crucial role of structural isomerism of the triazole group, which has been unsuspected for a long time although it can govern the geometry and electronic properties of rhenium complexes. It is shown for the first time that grafting a non-coordinated π-conjugated fragment on the N(4) atom of a 1,2,4-triazole group can be of high value for the design of efficient light-emitting materials based on rhenium complexes.
Published: 2018

21. Free-standing microcrystals of a fluorescent organic dye: Preparation and spectroscopic study

Author: Mouhammad Abyan, Liliana Bîrlă, Franck Bertorelle, Fernanda Rodrigues, and Suzanne Fery-Forgues
Subjects: Renewable energy sources, TJ807-830
Abstract: Suspensions of microcrystals were obtained from an organic fluorescent dye, 4-n-octylamino-7-nitrobenz-2-oxa-1,3-diazole, by reprecipitation in water in the presence of various macromolecules: anionic or cationic PAMAM dendrimer, poly(acrylic acid, sodium salt), poly(acrylamide), and calf thymus DNA. The use of these additives allowed the size and shape of the microcrystals to be controlled. A study by UV/vis absorption and fluorescence spectroscopy revealed some common points, but also some interesting differences, in the optical behaviour of the five samples.
Published: 2006
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22. Optimization of aggregation-induced phosphorescence enhancement in mononuclear tricarbonyl rhenium(I) complexes: the influence of steric hindrance and isomerism

Author: Jinhui Wang, Sonia Mallet-Ladeira, Suzanne Fery-Forgues, Jan Patrick Calupitan, Béatrice Delavaux-Nicot, Clémence Allain, Mariusz Wolff, Alexandre Poirot, Eric Benoist, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Institute of Drug Discovery Technology, Ningbo University, Ningbo University (NBU), State Key Laboratory of Chemical Oncogenomics, Tsinghua University, Laboratoire de chimie de coordination (LCC), Institute of Chemistry, Department of Crystallography, University of Silesia in Katowice, Université de Toulouse (UT), Laboratoire de Photophysique et Photochimie Supramoléculaires et Macromoléculaires (PPSM), École normale supérieure - Cachan (ENS Cachan)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ERC StG-715757 MECHANO-FLUO, Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)
Subjects: Steric effects, Quenching (fluorescence), 010405 organic chemistry, Ligand, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Substituent, chemistry.chemical_element, Rhenium, [CHIM.INOR]Chemical Sciences/Inorganic chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Inorganic Chemistry, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, chemistry.chemical_compound, Crystallography, chemistry, Moiety, Phenyl group, Phosphorescence
Abstract: International audience; In order to improve the remarkable performance of a mononuclear tricarbonyl rhenium(I) complex (ReL1) that exhibits rare aggregation-induced phosphorescence enhancement (AIPE) behavior, two new complexes (ReL3 and ReL4) were prepared and investigated. They incorporate a 2-pyridyl-1,2,4-triazole (pyta) ligand connected to a 2-phenylbenzoxazole (PBO) moiety. Complex ReL3 differs from ReL1 by the presence of a bulky tert-butyl substituent, and ReL4 is an isomer where the PBO group is linked to the pyta ligand by its phenyl group. Theoretical calculations were in congruence with electrochemical and spectroscopic properties in solutions. Both new compounds exhibited strong AIPE and much better solid-state emission efficiency than ReL1, with photoluminescence quantum yields up to 55% for ReL4. Crystallographic data indicate that this increase in emission efficiency is due to optimum packing that prevents quenching. This work shows that minor structural changes may have major effects upon the solid-state spectroscopic properties and it provides a rational basis for accessing AIPE-active strongly emissive rhenium(I) complexes.
Published: 2019

23. A review of Ni and Co incorporation during talc synthesis: Applications to crystal chemistry, industrial compounds and natural Ni- and Co-rich ore

Author: Mathilde Poirier, Pierre Micoud, Christophe Le Roux, Christel Carême, Manoela Prado, Sandra Einloft, Cyril Aymonier, Guillaume Aubert, Guilherme Dias, Cyril Quilfen, Marie Claverie, Angela Dumas, Suzanne Fery-Forgues, François Martin, Stefano Salvi, Géosciences Environnement Toulouse (GET), Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Observatoire Midi-Pyrénées (OMP), Météo France-Centre National d'Études Spatiales [Toulouse] (CNES)-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Météo France-Centre National d'Études Spatiales [Toulouse] (CNES)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Institut de Chimie de la Matière Condensée de Bordeaux (ICMCB), Université de Bordeaux (UB)-Institut Polytechnique de Bordeaux-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Faculdade de Química (FAQUI), Pontifícia Universidade Católica do Rio Grande do Sul [Porto Alegre] (PUCRS), IMERYS, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), the financial support from IMERYS Company, CAPES (Brazil government) and CNPq for DT grant (number 303467/2015-0)., Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut national des sciences de l'Univers (INSU - CNRS)-Observatoire Midi-Pyrénées (OMP), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National d'Études Spatiales [Toulouse] (CNES)-Centre National de la Recherche Scientifique (CNRS)-Météo-France -Institut de Recherche pour le Développement (IRD)-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National d'Études Spatiales [Toulouse] (CNES)-Centre National de la Recherche Scientifique (CNRS)-Météo-France -Centre National de la Recherche Scientifique (CNRS), Pontifical Catholic University of Rio Grande do Sul (PUC-RS), Imerys Aluminates, Institut de Chimie de Toulouse (ICT), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Ni, Mineral, Materials science, Crystal chemistry, Chemical fractionation, crystal growth, 02 engineering and technology, [CHIM.MATE]Chemical Sciences/Material chemistry, 010502 geochemistry & geophysics, 021001 nanoscience & nanotechnology, Talc, 01 natural sciences, Natural (archaeology), Synthesis, Chemical engineering, Geochemistry and Petrology, medicine, Economic Geology, 0210 nano-technology, Materials, 0105 earth and related environmental sciences, medicine.drug
Abstract: International audience; This article reviews the current knowledge on the incorporation of Ni and Co cations in mineral synthesis. In addition, it overviews the interest in developing such materials, and discusses a number applications in which these materials are used as mineral fillers. A reflection is then conducted showing that synthetic minerals rich in Ni and Co compare closely to those occurring in Ni- and Co-rich natural lateritic environment, which can thus be considered as mutual proxies. It follows that studies of lateritic environments can provide valuable information on formation processes of synthetic minerals, and vice versa. An example of cross-checking data between these two thematic fields is presented, which allows solving chemical fractionation problems encountered in lateritic environments.
Published: 2019

24. Mechanofluorochromic Properties of an AIEE-Active 2-Phenylbenzoxazole Derivative: More than Meets the Eye?

Author: Chantal Carayon, Ross Brown, Nathalie Saffon-Merceron, Nadine Leygue, Abdelhamid Ghodbane, Suzanne Fery-Forgues, Jinhui Wang, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux (IPREM), Université de Pau et des Pays de l'Adour (UPPA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-17-CE07-0029,SUPERFON,Synthèse de nanocristaux organiques fluorescents en milieu fluide supercritique: une approche numérique et expérimentale complémentaire(2017), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and Université de Toulouse (UT)
Subjects: Materials science, Photoluminescence, aggregation-induced emission, Exciton, 02 engineering and technology, 010402 general chemistry, Photochemistry, 01 natural sciences, waveguiding, Analytical Chemistry, chemistry.chemical_compound, mechanofluorochromism, Physical and Theoretical Chemistry, Aggregation-induced emission, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, 021001 nanoscience & nanotechnology, Fluorescence, 0104 chemical sciences, Amorphous solid, Solvent, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, benzoxazole, chemistry, 13. Climate action, Crystallite, fluorescence, 0210 nano-technology, Derivative (chemistry)
Abstract: International audience; The presence of a dicyanovinyl group on the robust 2‐phenylbenzoxazole framework led to the emergence of aggregation‐induced emission enhancement (AIEE) characteristics. A mechanofluorochromic (MFC) behaviour was observed. The pristine microcrystals emitted yellow‐green light, which became golden yellow upon grinding, with the reverse process observed upon heating or solvent fuming. This phenomenon was accompanied by a reversible evolution of the photoluminescence quantum yields and lifetimes. These variations were attributed to the formation of different types of emissive species in the crystalline phases and in the ground material, which is a mixture of very small microcrystals and amorphous matter. Remarkably, evidence was also given for other spectroscopic effects, which depend on the size, compactness and heterogeneity of the solid samples. These effects are presumably linked to the generation of regions rich in low‐energy exciton traps in polycrystalline and pressed samples, and to light reabsorption. They are enhanced by the fact that the pristine platelets exhibit self‐waveguided edge emission, and they are all the more significant as the MFC effect is rather weak.
Published: 2019

25. Conjugates of Benzoxazole and GFP Chromophore with Aggregation-Induced Enhanced Emission: Influence of the Chain Length on the Formation of Particles and on the Dye Uptake by Living Cells

Author: Chantal Carayon, Suzanne Fery-Forgues, Abdelhamid Ghodbane, Laure Gibot, Kyril M. Solntsev, Nathalie Saffon, Rémy Dumur, Jinhui Wang, Marie-Pierre Rols, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de pharmacologie et de biologie structurale (IPBS), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Structure Fédérative Toulousaine en Chimie Moléculaire (SFTCM), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)
Subjects: Chemical structure, Green Fluorescent Proteins, Nanoparticle, 02 engineering and technology, 010402 general chemistry, Photochemistry, 01 natural sciences, Biomaterials, chemistry.chemical_compound, [CHIM]Chemical Sciences, Organic chemistry, Molecule, General Materials Science, ComputingMilieux_MISCELLANEOUS, Alkyl, Fluorescent Dyes, chemistry.chemical_classification, Benzoxazoles, General Chemistry, Benzoxazole, Chromophore, 021001 nanoscience & nanotechnology, Fluorescence, 0104 chemical sciences, Solvent, chemistry, Nanoparticles, Microscopy, Electrochemical, Scanning, 0210 nano-technology, Biotechnology
Abstract: Six conjugates of benzoxazole and green fluorescent protein chromophore that differ by the length of their alkyl chain (from C1 to C16) are investigated. They exhibit rigidofluorochromism and clear aggregation-induced emission enhancement (AIEE) behavior with emission in the orange-red that is specific to the solid state. A preparation method based on solvent exchange is used to prepare particles. The self-association properties of these molecules depend on the length of the alkyl chain. Microfibers, platelets, and rounded microparticles are successively obtained by increasing the chain length. The same method is used to prepare nanoparticles (NPs) that are fully characterized. In particular, homogeneous populations of stable NPs measuring around 70 nm are obtained with the analogs whose chains contain four to eight carbon atoms. The behavior with respect to living cells is also influenced by the nature of the compounds. Only the dyes with intermediate hydrophobicity are efficiently uptaken by both normal and tumor cells, and fluorescence only originates from dispersed dye molecules. There is no evidence for incorporation of NPs into cells. This work shows that small variations of the chemical structure must be taken into account for making the best use of AIEE compounds in view of precise applications.
Published: 2016

26. From 2-phenylbenzoxazole to diphenyl-bibenzoxazole derivatives: Comparative advantages of mono- and bis-chromophores for solution and solid-state fluorescence

Author: Patrice Bordat, Sylvie Blanc, Suzanne Fery-Forgues, Nathalie Saffon, Abdelhamid Ghodbane, Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux (IPREM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Pau et des Pays de l'Adour (UPPA), Structure Fédérative Toulousaine en Chimie Moléculaire (SFTCM), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Photoluminescence, Optical properties, Chemistry, Process Chemistry and Technology, General Chemical Engineering, Solid-state, 02 engineering and technology, Conjugated system, Chromophore, Crystal structure determination, DFT calculations, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, Fluorescence, Non-doped emitter, 0104 chemical sciences, Para position, Fluorescent probes, [CHIM]Chemical Sciences, Molecule, Absorption (chemistry), 0210 nano-technology
Abstract: cited By 1; International audience; The optical properties of three bis-benzoxazole derivatives, namely 2,2’-diphenyl-6,6’-bibenzoxazole and its derivatives bearing methyl and tert-butyl groups at the para position, were investigated and compared to those of the corresponding subunits. As expected from the increase of the π-electron conjugated system, the absorption and fluorescence spectra were red-shifted when passing from mono-to bis-chromophores. The three bis-benzoxazoles showed superior fluorescence quantum yields in solution, but they were only weakly emissive in the solid state, the unsubstituted derivative even being virtually not photoluminescent. The solid-state behaviour was explained by the fact that bis-chromophoric molecules were locked in a non-planar conformation, as discussed on the basis of DFT calculations and X-ray data.
Published: 2016

27. Effects of the benzoxazole group on green fluorescent protein chromophore crystal structure and solid state photophysics

Author: Laren M. Tolbert, Kyril M. Solntsev, John R. Bright, Debashree Ghosh, W. Brett Fellows, Nathalie Saffon, Suzanne Fery-Forgues, and Abdelhamid Ghodbane
Subjects: chemistry.chemical_classification, Chemistry, Quantum yield, 02 engineering and technology, General Chemistry, Crystal structure, Chromophore, Benzoxazole, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, Excimer, 01 natural sciences, 0104 chemical sciences, Green fluorescent protein, chemistry.chemical_compound, Group (periodic table), Materials Chemistry, 0210 nano-technology, Alkyl
Abstract: Four benzoxazole-substituted GFP chromophores that differ by the length of their alkyl chain (from C1 to C12) were synthesized. In solution, the four compounds showed identical spectroscopic behavior, emitting blue light with moderate quantum yield. In the solid state, the butyl, pentyl and dodecyl derivatives strongly emitted orange light, while the methyl derivative was only weakly emissive. Based on the X-ray data and DFT calculations, emission in the solid state was explained by the formation of excimers. A very unusual “hot-dog”-type excimer was found for the dodecyl derivative, in which two overlapping chromophores are separated by an alkyl chain.
Published: 2016

28. Fluorescent organic ion pairs based on berberine: counter-ion effect on the formation of particles and on the uptake by colon cancer cells

Author: Céline Frongia, Marine Soulié, Valérie Lobjois, Suzanne Fery-Forgues, Institut des Technologies Avancées en sciences du Vivant (ITAV), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Laboratoire de Biologie Cellulaire et Moléculaire du Contrôle de la Prolifération (LBCMCP), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre de Biologie Intégrative (CBI), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chemistry.chemical_classification, Tetraphenylborate, Aqueous solution, General Chemical Engineering, Salt (chemistry), Nanoparticle, General Chemistry, Fluorescence, chemistry.chemical_compound, Berberine, chemistry, Dynamic light scattering, [CHIM]Chemical Sciences, Organic chemistry, Counterion, ComputingMilieux_MISCELLANEOUS, Nuclear chemistry
Abstract: Four organic salts of berberine, a natural alkaloid, were prepared, characterized and studied for their fluorescence properties in solution and in the solid state. Aqueous suspensions of salt-based nanoparticles (NPs) were generated using the ion association technique. The amount and size of the formed NPs were examined by UV-vis absorption spectroscopy, dynamic light scattering and transmission electron microscopy. They were closely dependent upon the nature of the salt and the experimental conditions of preparation. For instance, the four organic salts formed NPs in water, while only the tetraphenylborate salt (Ber+TPB−) was shown to give stable particles in the cell culture medium, i.e. Opti-MEM supplemented by fetal calf serum. The behaviour of these salts placed in contact with cells was investigated. All berberine salts entered the cells and were detected in the reticulum and mitochondria. However, the cell fluorescence was much stronger for Ber+TPB− than for the other salts. It could not be ascertained whether this effect was attributable to the intrinsic chemical properties of the Ber+TPB− salt or to the presence of nanoparticles. The nature of the anion also influenced the dye diffusion within the cells under illumination. A strong phototoxic effect was observed. This study showed the interest of using organic salts for improved uptake of active compounds, and underlined the potential of carrier-free nano- and submicrometric particles for therapy, phototherapy and diagnosis.
Published: 2015

29. 2-Phenylbenzoxazole derivatives: a family of robust emitters of solid-state fluorescence

Author: Suzanne Fery-Forgues, Chantal Carayon, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Photoluminescence, 02 engineering and technology, Benzoxazole, Conjugated system, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, 0104 chemical sciences, Crystal, chemistry.chemical_compound, chemistry, Intramolecular force, Molecule, [CHIM]Chemical Sciences, Thermal stability, Physical and Theoretical Chemistry, 0210 nano-technology, Dispersion (chemistry), ComputingMilieux_MISCELLANEOUS
Abstract: The derivatives of 2-phenylbenzoxazole (PBO) are popular fluorescent organic dyes for use in solution or after dispersion in an appropriate matrix. Their spectroscopic behavior in the solid state is, unjustly, not so well known. Many of them are strongly emissive as pure solid dyes, due to a favorable crystal packing mode. The PBO fragment lends itself well to relatively simple modifications of its chemical structure, aimed at enlarging the conjugated π-electron system. Many molecules thus designed show aggregation-induced emission (AIE). Furthermore, the derivatives of 2-(2'-hydroxyphenyl)benzoxazole (HBO) are familiar excited-state intramolecular proton transfer (ESIPT) dyes. They are particularly well suited for solid-state sensing. Mechanofluorochromism is also observed in complexes and closely-related compounds. Regarding their self-association properties, the general tendency of many PBO derivatives is to give elongated nano and microparticles. Very small chemical changes are enough to tune the shape and size of these particles. Nanofibers may be obtained by simple preparation methods and are of great value for wave-guiding. For all these reasons, as well as for its robustness and high photo- and thermal stability, the PBO fragment is an attractive building block to access new molecules that will be particularly well adapted for developments in the field of photoluminescent materials.
Published: 2017

30. Investigations in the methoxy-iminocoumarin series: Highly efficient photoluminescent dyes and easy preparation of green-emitting crystalline microfibers

Author: Nihel Abid-Jarraya, Nathalie Saffon, Suzanne Fery-Forgues, Souhir Abid, Kacem Khemakhem, and Hamida Turki-Guermazi
Subjects: Materials science, business.product_category, Photoluminescence, High interest, Process Chemistry and Technology, General Chemical Engineering, Solid-state, Photochemistry, Fluorescence, Solvent, Microfiber, Fluorescent materials, Luminescence, business
Abstract: The fluorescence properties of four methoxy derivatives of 3-cyano-2-(N-ethoxycarbonyl)iminocoumarin, differing by the position and number of the methoxy substituents, were investigated. The 8-methoxy-iminocoumarin derivative was virtually non-fluorescent. The 7-methoxy-iminocoumarin derivative was only weakly fluorescent both in solution and in the solid state. The 6-methoxy-iminocoumarin derivative was poorly fluorescent in every solvent investigated, but it showed high photoluminescence in the solid state. To our knowledge, this is the first example of crystallization-enhanced emission (CEE) in the iminocoumarin series. The mechanism probably encompasses restricted rotation and favorable molecular packing. Moreover, this compound spontaneously crystallized as long microfibers. The 5,7-dimethoxy-iminocoumarin derivative exhibited good fluorescence in very polar solvents and was intensely luminescent in the crystalline state. The last two substitution patterns, 6-methoxy and 5,7-dimethoxy, could be of high interest for the design of new fluorescent materials.
Published: 2014

31. Spectroscopic study of 3-aryl-7-methoxy-coumarin, iminocoumarin and bis-iminocoumarin derivatives in solution

Author: Rachid El Gharbi, Suzanne Fery-Forgues, Houcine Ammar, Souhir Abid, and Kacem Khemakhem
Subjects: chemistry.chemical_compound, chemistry, Emission efficiency, Process Chemistry and Technology, General Chemical Engineering, Aryl, Dimer, Photochemistry, Coumarin, Fluorescence
Abstract: 3-Phenyl-5,7-dimethoxycoumarin and 3-(2-thienyl)-7-methoxycoumarin were strongly fluorescent in organic solution, with quantum yields reaching 0.84. In contrast, the iminocoumarin analogs of these dyes were poorly emissive. This shows that the behaviour of coumarins cannot be systematically transposed to their iminocoumarin analogs. The spectroscopic properties of iminocoumarin dimers were also examined. These dimers present little spectroscopic interest in comparison with the parent compounds. Above all, this study indicates the untapped potential of fluorescent 3-aryl-7-methoxycoumarins, which have scarcely been studied. In particular, 3-(2-thienyl)-7-methoxycoumarin exhibited good emission efficiency in a wide range of solvents, and could be very useful as a fluorescent label including in protic media.
Published: 2013

32. Blue-Emitting Nanocrystals, Microcrystals, and Highly Oriented Nanofibers Prepared by Reprecipitation and Solvent Drop-Casting of 2-Phenyl-naphthoxazoles

Author: Rachid Mahiou, Nathalie Saffon, J.P. Galaup, Suzanne Fery-Forgues, Abdelhamid Ghodbane, and Jérémy Colléaux
Subjects: Materials science, Photoluminescence, Substituent, Nanoparticle, Quantum yield, Crystal growth, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Nanocrystal, Chemical engineering, Nanofiber, Organic chemistry, 0210 nano-technology, Tetrahydrofuran
Abstract: Three 2-phenyl-naphth[2,3-d]oxazole derivatives, one of them being unsubstituted (1) and the two others bearing a methyl (2) and a tert-butyl group (3) in the para position of the phenyl ring, were prepared. In the crystalline state, all compounds adopted a crossed-stacking mode that favors fluorescence emission. They emitted in the blue region and their photoluminescence quantum yield ranged between 25 and 59 %. The preparation of micro/nanoparticles by simple methods was optimized. By using a solvent-exchange method, the compounds readily gave microcrystals, the size and shape of which closely depend on the nature of the substituent, as well as nanocrystals that measured around 200 nm. The proportion of micro- and nanocrystals was modulated by the experimental conditions and the two populations could be separated by filtration for subsequent use. For unsubstituted compound 1, drop-casting from a solution in tetrahydrofuran spontaneously generated an array of parallel and almost perpendicularly oriented nanofibers that exhibited efficient waveguiding properties. Owing to their robustness, good solid-state optical properties, and to the simplicity of particle preparation, these naphthoxazole derivatives appear as promising candidates for the fabrication of blue-emitting tracers and nanofibers.
Published: 2012

33. A comparative study of nine berberine salts in the solid state: optimization of the photoluminescence and self-association properties through the choice of the anion

Author: Suzanne Fery-Forgues, Sylvie Blanc, Chantal Carayon, Nathalie Saffon, Marine Soulié, Institut des Technologies Avancées en sciences du Vivant (ITAV), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Structure Fédérative Toulousaine en Chimie Moléculaire (SFTCM), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT), Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux (IPREM), Université de Pau et des Pays de l'Adour (UPPA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)
Subjects: Photoluminescence, Fluorophore, biology, Chemistry, Inorganic chemistry, General Physics and Astronomy, Ionic bonding, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Fluorescence, 0104 chemical sciences, Ion, chemistry.chemical_compound, Berberine, Berberine Chloride, biology.protein, [CHIM]Chemical Sciences, Physical and Theoretical Chemistry, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS, Organic anion
Abstract: The arrangement of an ionic fluorophore in the crystalline state was regulated by the presence of various counter-ions and the effect on spectroscopic and self-association properties was studied. To do so, nine salts of berberine (i.e. a fluorescent natural alkaloid) were investigated. Most of them contained organic anions and were prepared using an ion-exchange process. Berberine chloride and hemisulfate were also used for the sake of comparison. The diffuse reflectance and photoluminescence spectra were recorded on powder compounds. All salts were emissive in the solid state and the emission efficiency was increased seven-fold with the nature of the anion. The optical properties were tentatively discussed on the basis of the crystal-packing mode. The possibility of implementing a bottom-up approach to generate microparticles was investigated using the reprecipitation method. Salts that contain the most hydrophobic anions gave a large number of homogeneous, elongated microparticles. This study showed that most of the berberine salts could be used as fluorescent materials, but proper choice of the anion allows using the self-association properties to best advantage.
Published: 2016

34. Fluorescent nanofibers and microcrystals obtained by reprecipitation of a long-chain iminocoumarin derivative

Author: Nathalie Saffon, Souhir Abid, Hamida Turki, and Suzanne Fery-Forgues
Subjects: Materials science, Process Chemistry and Technology, General Chemical Engineering, Crystal structure, Fluorescence, Nanomaterials, Crystal, Solvent, chemistry.chemical_compound, chemistry, Chemical engineering, Nanofiber, Organic chemistry, Acetonitrile, Derivative (chemistry)
Abstract: An iminocoumarin derivative bearing a fatty chain, specifically N-palmitoyl-3-cyano-7-diethylamino-2-iminocoumarin, was synthesized and used to prepare particles owing to a solvent exchange process (reprecipitation method). The composition of the reprecipitation medium was allowed to vary. In all cases, very thin particles that emitted yellow–orange light were obtained. In water alone, they looked like nanofibers or nanoribbons. Addition of surfactants at concentrations lower than the CMC favored the formation of bladed microcrystals. In the presence of acetonitrile, elongated microcrystals with good wave-guiding properties were obtained. The fluorescence properties were discussed on the basis of the crystal packing mode. It appears that the flexibility of the imino function leads to an original crystal structure, which is compatible with solid-state fluorescence. This property, together with the ease of synthesis, makes this family of compounds interesting for subsequent use as optically-active nanomaterials.
Published: 2012

35. Facile Access to Highly Fluorescent Nanofibers and Microcrystals via Reprecipitation of 2-Phenyl-benzoxazole Derivatives

Author: Luca Scarpantonio, Pascale Jolinat, Abdelhamid Ghodbane, Sébastien D’Altério, Nathalie Saffon, Nathan D. McClenaghan, and Suzanne Fery-Forgues
Subjects: chemistry.chemical_classification, Benzoxazoles, Aqueous solution, Photoluminescence, Nanofibers, Substituent, Surfaces and Interfaces, Benzoxazole, Crystallography, X-Ray, Condensed Matter Physics, Photochemistry, Fluorescence, Nanomaterials, chemistry.chemical_compound, chemistry, Electrochemistry, Alkoxy group, Organic chemistry, General Materials Science, Crystallization, Spectroscopy, Alkyl, Fluorescent Dyes
Abstract: 2-Phenyl-benzoxazole and five derivatives bearing an alkyl or alkoxy substituent on the phenyl ring were used to prepare aqueous suspensions of particles via a solvent-exchange method. In these conditions, the methyl and methoxy derivatives spontaneously gave nanofibers, while the other compounds led to microcrystals. This shows that minor chemical changes are enough to direct the formation of a given type of particle. From a spectroscopic viewpoint, all compounds strongly emit blue light in the solid state, with spectra much broader than those registered in n-heptane and ethanol solutions. The photoluminescence quantum yields reached 38% and were slightly affected in aqueous suspension by the polarity of the environment. The molecular arrangement, deduced from X-ray analysis for the methyl and methoxy derivatives, was used to explain the fluorescence properties in the solid state. This work shows that 2-phenyl-benzoxazole derivatives are interesting candidates for applications as fluorescent nanomaterials, including in aqueous and biological media.
Published: 2011

36. Dipolar versus Octupolar Triphenylamine-Based Fluorescent Organic Nanoparticles as Brilliant One- and Two-Photon Emitters for (Bio)imaging

Author: Suzanne Fery-Forgues, Gaëlle Recher, Mireille Blanchard-Desce, Venkatakrishnan Parthasarathy, Francesca Terenziani, and Elisa Campioli
Subjects: Diagnostic Imaging, Materials science, Analytical chemistry, Quantum yield, Nanoparticle, Photochemistry, Triphenylamine, Absorption, Biomaterials, Xenopus laevis, chemistry.chemical_compound, Suspensions, X-Ray Diffraction, Animals, General Materials Science, Amines, Fluorescent Dyes, Photons, Aqueous solution, Diphenylamine, Absorption cross section, General Chemistry, Chromophore, Fluorescence, Spectrometry, Fluorescence, chemistry, Quantum dot, Solvents, Nanoparticles, Spectrophotometry, Ultraviolet, Biotechnology
Abstract: Two related triphenylamine-based dipolar and octupolar fluorophores are used to prepare aqueous suspensions of fluorescent organic nanoparticles (FONs) via the reprecipitation method. The obtained spherical nanoparticles (30-40 nm in diameter) are fluorescent in aqueous solution (up to 15% fluorescence quantum yield) and exhibit extremely high one- and two-photon brightness, superior to those obtained for quantum dots. Despite the two chromophores showing similar fluorescence in solution, the fluorescence of FONs made from the octupolar derivative is significantly red-shifted compared to that generated by the dipolar FONs. In addition, the maximum two-photon absorption cross section of the FONs made from the octupolar derivative is 55% larger than that of the dipolar derivative FONs. The experimental observations provide evidence that the different molecular shape (rodlike versus three-branched) and charge distribution (dipolar versus octupolar) of the two chromophores strongly affect the packing inside the nanoparticles as well as their spectroscopic properties and colloidal stability in pure water. The use of these FONs as probes for biphotonic in-vivo imaging is investigated on Xenopus laevis tadpoles to test their utilization for angiography. When using FONs made from the octupolar dye, the formation of microagglomerates (2-5 μm scale) is observed in vivo, with subsequent lethal occlusion of the blood vessels. Conversely, the nanoparticles of the dipolar dye allow acute imaging of blood vessels thanks to their suitable size and brightness, while no toxic effect is observed. Such a goal cannot be achieved with the dissolved dye, which permeates the vessel walls.
Published: 2011

37. Spontaneous Formation of Fluorescent Nanofibers and Reticulated Solid from Berberine Palmitate: A New Example of Aggregation-Induced Emission Enhancement in Organic Ion Pairs

Author: Nathalie Saffon, Joe Chahine, Suzanne Fery-Forgues, and Martine Cantuel
Subjects: chemistry.chemical_classification, Quenching (fluorescence), Aqueous solution, Analytical chemistry, Salt (chemistry), Surfaces and Interfaces, Condensed Matter Physics, Photochemistry, Fluorescence, Suspension (chemistry), chemistry, Nanofiber, Electrochemistry, Fluorescence microscope, Particle, General Materials Science, Spectroscopy
Abstract: The salt formed between the large aromatic berberine cation and the long-chain palmitate anion was synthesized and used to prepare aqueous suspensions of particles owing to a solvent-exchange method. Under these conditions, elongated particles were readily obtained. They were studied by transmission microscopy with polarized light, as well as by fluorescence and electron microscopy. They were shown to be probably crystallized nanofibers, which were stable in suspension. Unexpectedly, upon filtration and drying, these fibers evolved to give a reticulated solid. The fluorescence properties of the compound were analyzed in solution, in aqueous suspension and in the powder crystalline state. Interestingly, berberine palmitate is virtually not fluorescent in aqueous solution because of the quenching effect of water, but transition to the solid state was accompanied by a strong increase in fluorescence intensity. This phenomenon was explained by the original molecular arrangement in the solid state. Actually, in the crystal, the anions form a distinct layer, which limits parallel-stacking of the fluorescent cations. Moreover, the berberine cations are protected from the access of water molecules, and so no quenching effect can take place. This example confirms that the newly introduced concept of ion-pair aggregation-induced fluorescence enhancement can be extended to a variety of structures. It also shows the interest of ion pairs for preparing fluorescent nanofibers and reticulated solids using a solvent-exchange method that is particularly easy to implement.
Published: 2011

38. Searching for fluorescent nanocrystals in aqueous solutions of 7-methoxycoumarin

Author: Clara Fournier-Noël, Martine Cantuel, and Suzanne Fery-Forgues
Subjects: Absorbance, Aqueous solution, Nanocrystal, Dynamic light scattering, Chemistry, Process Chemistry and Technology, General Chemical Engineering, Nanoparticle, Quantum yield, Photochemistry, Fluorescence, Fluorescence spectroscopy
Abstract: The unexpected formation of nanocrystals in dilute dye solutions was revealed using the hydrophobic dye, 7-methoxycoumarin, the spectroscopic behavior of which has been frequently studied in water; comparison was made with the water-soluble, sulfonated analogue. A solution of the dye at 10 −5 M concentration range was found to be a suspension of nanocrystals; at concentrations of 1 × 10 −4 M, > 70% dye was in the form of nanocrystals. Surprisingly, the presence of these nanocrystals was difficult to detect by routine absorbance and fluorescence spectroscopy and was mainly noticeable by measurement of fluorescence quantum yield, as the nanocrystals were poorly emissive compared to dissolved dye molecules; electron microscopy and dynamic light scattering gave clear evidence for the presence of nanocrystals. This article illustrates the fact that the formation of nanocrystals, although abundant, may easily go unnoticed.
Published: 2010

39. Convenient Synthesis of a New Series of 3-Triazolonyl Iminocoumarins

Author: Rachid El Gharbi, Hamida Turki, Suzanne Fery-Forgues, and Myriam Kammoun
Subjects: chemistry.chemical_compound, Series (mathematics), Infrared, Elemental analysis, Chemistry, Organic Chemistry, Proton NMR, Organic chemistry, One-Step, Carbon-13 NMR, Dichloromethane
Abstract: 3-Cyano-7-diethylamino-N-ethoxycarbonyl-iminocoumarin reacted with different hydrazines as N-nucleophiles to afford, in one step, a new series of 2-N-substituted 3-triazolonyl-iminocoumarins in good yields. In two cases, N-unsubstituted derivatives were also obtained. The structures of all the products obtained were confirmed by infrared, 1H NMR, 13C NMR, and elemental analysis. The optical properties of three of these compounds in dichloromethane and ethanol were reported.
Published: 2010

40. Aggregation-Induced Emission Enhancement in Organic Ion Pairs

Author: Jean-François Lamère, Nathalie Saffon, Suzanne Fery-Forgues, and Isabelle Dos Santos
Subjects: chemistry.chemical_classification, Chemistry, Inorganic chemistry, Nanoparticle, Salt (chemistry), Surfaces and Interfaces, Condensed Matter Physics, Fluorescence, Ion, chemistry.chemical_compound, Electrochemistry, Molecule, Phenol, General Materials Science, Ammonium, Phenols, Spectroscopy
Abstract: We present here a new example of aggregation-induced emission enhancement (AIEE), which involves an original mechanism based on the formation of organic ion pairs. The phenol 4-hydroxy-7-nitrobenzoxadiazole (NBDOH) is dissociated in water at pH 5.0 to give the corresponding phenolate, which is poorly fluorescent in this medium. We bring evidence that fluorescence quenching is due to an interaction with water molecules. In the presence of a relatively bulky ammonium salt, specifically tetrabutylammonium bromide (TBAB), NBDOH forms a hydrophobic salt, TBA(+)NBDO(-). This has no influence on the fluorescence of the anion as long as the salt is dissolved. However, the salt readily crystallizes in the medium and transition to the solid state is accompanied by a strong increase in fluorescence intensity. This effect can be explained by two reasons. The anions are protected from water molecules, and above all, the presence of the bulky cations prevents parallel-stacking of the anions, thus leading to an original molecular arrangement that is favorable to fluorescence. As the nature of the organic cation may be easily changed, the versatility of the system is very interesting for the design of new organic micro- and nanoparticles that must be fluorescent in the solid state, possibly in an aqueous environment.
Published: 2010

41. The synthesis and optical properties of novel fluorescent iminocoumarins and bis-iminocoumarins: Investigations in the series of urea derivatives

Author: Suzanne Fery-Forgues, Mehdi Fakhfakh, Rachid El Gharbi, and Hamida Turki
Subjects: chemistry.chemical_compound, chemistry, Elemental analysis, Process Chemistry and Technology, General Chemical Engineering, Proton NMR, Substituent, Carbon-13 NMR, Mass spectrometry, Photochemistry, Fluorescence, Fluorescence spectroscopy, Dichloromethane
Abstract: The condensation of 3-cyano-7-diethylamino-iminocoumarin with various isocyanates and diisocyanates as C-electrophiles gave a new series of N-substituted iminocoumarins and bis-iminocoumarins. The ten compounds obtained were characterized using IR, 1 H NMR, 13 C NMR, elemental analysis and mass spectrometry. Their optical properties, studied in dichloromethane by UV/vis absorption and fluorescence spectroscopy, were found to depend strongly upon the nature of the substituent borne by the imino group. For the sake of comparison, the optical properties of selected compounds were also analyzed in ethanol. Of the iminocoumarins studied, the alkylurea derivatives displayed the most interesting spectroscopic characteristics and may be of potential use as novel fluorescent probes in media of various polarity.
Published: 2010

42. Suspensions of Organic Microcrystals Produced in the Presence of Polymers: Diversity of UV/Vis Absorption and Fluorescence Properties According to the Preparation Conditions

Author: Mouhammad Abyan, Dominique de Caro, and Suzanne Fery-Forgues
Subjects: Absorption spectroscopy, Polymers, Scanning electron microscope, Analytical chemistry, law.invention, Microscopy, Electron, Transmission, X-Ray Diffraction, law, Spectrophotometry, Microscopy, Electrochemistry, medicine, General Materials Science, Organic Chemicals, Crystallization, Spectroscopy, chemistry.chemical_classification, Molecular Structure, medicine.diagnostic_test, Chemistry, Surfaces and Interfaces, Polymer, Condensed Matter Physics, Fluorescence, Transmission electron microscopy, Microscopy, Electron, Scanning
Abstract: Free-standing microcrystals of an organic fluorescent dye, specifically, 4-n-octylamino-7-nitrobenz-2-oxa-1,3-diazole, were prepared using a solvent-exchange process at room temperature, in the presence of polymers used as additives. Parameters such as the dye concentration, the nature and concentration of the polymer, and the pH of the solution were varied. Six samples of microcrystals were therefore obtained and characterized by fluorescence microscopy and by electron microscopy (TEM and SEM). They differed by their content in microcrystals, the shape and size of which depends strongly on experimental conditions. Curiously, the UV/vis absorption spectra of the microcrystal suspensions were very different from one sample to another. As a result the emission spectra were also varied. The diversity of the optical response obtained was attributed to the presence of several dye populations in the microcrystal suspensions. A distinction was made between the intrinsic spectral properties of the microcrystals and artifacts due to the presence of the additives.
Published: 2009

43. Reactivity of 3-cyano-N-ethoxycarbonyl-iminocoumarin with hydrazides as N-nucleophiles

Author: Hamida Turki, Suzanne Fery-Forgues, Myriam Kammoun, and Rachid El Gharbi
Subjects: Nucleophile, Chemistry, Organic Chemistry, Organic chemistry, Reactivity (chemistry)
Published: 2009

44. Nano- and Microparticles of Organic Fluorescent Dyes

Author: Mouhammad Abyan, Jean-François Lamère, and Suzanne Fery-Forgues
Subjects: Aqueous solution, Materials science, General Neuroscience, Nanoparticle, Nanotechnology, Fluorescence, General Biochemistry, Genetics and Molecular Biology, Suspension (chemistry), History and Philosophy of Science, Chemical engineering, Nano, Photocatalysis, Crystal habit, Absorption (chemistry)
Abstract: Organic nanostructured materials are of increasing interest for applications in the fields of bioanalysis, photocatalysis, photonics, and organic light-emitting diodes. However, their preparation is still difficult to control and their optical properties are inadequately known. A solvent-exchange process called the "reprecipitation method" was used here to prepare nano- and microcrystals from fluorescent dyes belonging, for example, to the coumarin and nitrobenzoxadiazole (NBD) series. Typically, the dyes were dissolved in a hydrophilic organic solvent and then suddenly placed in an aqueous environment, where they spontaneously produce molecular assemblies. According to the self-association properties of the dyes and to the experimental conditions used, the nano- and microcrystals obtained exhibited different sizes and shapes, as observed by fluorescence and electron microscopy. In some cases, the crystal habit was controlled by adding some additives to the reprecipitation medium. The overall optical properties of the free-standing particles in suspension were generally quite close to those of the dissolved dyes. However, strong distortions of the absorption and emission spectra were observed for crystals grown in the presence of ionic additives. Under the fluorescence microscope, individual microcrystals may show peculiar emission characteristics, displaying bright and dark zones, or behaving like tiny optical fibers.
Published: 2008

45. Self-assembly properties of some chiral N-palmitoyl amino acid surfactants in aqueous solution

Author: Jean-François Lamère, Fernanda Rodrigues, Mariana Gerova, Suzanne Fery-Forgues, and A. Dobrev
Subjects: chemistry.chemical_classification, Circular dichroism, Aqueous solution, Chemistry, Circular Dichroism, Palmitic Acid, Stereoisomerism, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Amino acid, Solutions, Biomaterials, Surface-Active Agents, Colloid and Surface Chemistry, Microscopy, Electron, Transmission, Dynamic light scattering, Polymer chemistry, Scattering, Radiation, Organic chemistry, Racemic mixture, Amino Acids, Threonine, Enantiomer, Chirality (chemistry), Nuclear Magnetic Resonance, Biomolecular
Abstract: Various chiral N-palmitoyl amino acid surfactants (AAS) derived from methionine, proline, leucine, threonine, phenylalanine and phenylglycine were prepared and converted to their sodium salt. The properties of the aggregates formed in aqueous solution were studied for both the optically-active compounds and their racemic mixture. Characterization was made by surface tensiometry, fluorimetry, dynamic light scattering, circular dichroism (CD) and transmission electron microscopy. It appeared that most of the AAS studied in this work spontaneously formed different types of aggregates, including micrometer-sized aggregates. No significant difference could be found between the critical aggregation concentration (cac) value of pure enantiomers and that of the racemic forms. CD spectra did not reveal any aggregation-induced chirality.
Published: 2008

46. Fluorescent Microcrystals Obtained from Coumarin 6 Using the Reprecipitation Method

Author: Suzanne Fery-Forgues, Rami El-Ayoubi, and Jean-François Lamère
Subjects: Sociology and Political Science, Chemistry, Clinical Biochemistry, Solid-state, Photochemistry, Coumarin, Biochemistry, Fluorescence, Clinical Psychology, chemistry.chemical_compound, Transmission electron microscopy, Acetone, Fluorescence microscope, Absorption (chemistry), Law, Spectroscopy, Social Sciences (miscellaneous)
Abstract: The reprecipitation method was applied to Coumarin 6. A concentrated solution of the dye in acetone was mixed at room temperature with a large volume of water, and microcrystals rapidly appeared in the medium. Their size and shape were visualized by fluorescence microscopy, as well as by transmission electron microscopy. The absorption and fluorescence properties were studied on the suspensions and compared with those of the dissolved dye. This study is aimed at clarifying the influence of the reprecipitation process upon the fluorescence properties of the dye in the solid state.
Published: 2008

47. Spontaneous Formation of Fluorescent Nanofibers from Self-Assembly of Low-Molecular-Weight Coumarin Derivatives in Water

Author: Suzanne Fery-Forgues, Jean-François Lamère, Fernanda Rodrigues, and Marion Mille
Subjects: Surface Properties, Scanning electron microscope, Stereochemistry, Crystal structure, Photochemistry, Microscopy, Electron, Transmission, Coumarins, Electrochemistry, General Materials Science, Fiber, Particle Size, Spectroscopy, Fluorescent Dyes, Aqueous solution, Molecular Structure, Chemistry, Water, Surfaces and Interfaces, Condensed Matter Physics, Fluorescence, Molecular Weight, Spectrometry, Fluorescence, Transmission electron microscopy, Nanofiber, Nanoparticles, Spectrophotometry, Ultraviolet, Self-assembly
Abstract: A solvent-exchange process was applied to three fluorescent dyes belonging to the 2-benzimidazolyl-7-diethylaminocoumarin series (namely Coumarin 7 (1), Coumarin 30 (2), and one of their derivatives bearing a butyl chain (3)). The three compounds only differ by the substitution of the nitrogen atom of the benzimidazolyl group. They were first dissolved in acetone and then suddenly placed in an aqueous environment where they generated molecular assemblies. The size and shape of the latter were studied by fluorescence microscopy and transmission and scanning electron microscopy. It appeared that 1 gave aggregates and flat microcrystals that evolved toward elongated structures. 2 formed straight nanofibers that are 10-20 microm long and exhibit a crystal structure. 3 gave short fibers (1 micromx25 nm), which finally arrange into entangled solid nanofibers. The formation of fibers arising from low-molecular-weight molecules was particularly interesting. The optical properties of the free-standing particles in suspension were analyzed and compared to those of highly dilute dyes, with the aim to get additional information about the dye arrangement in the nanostructures.
Published: 2008

48. Synthesis and spectroscopic study of new biscoumarin dyes based on 7-(4-methylcoumarinyl) diesters

Author: Suzanne Fery-Forgues, Souhir Abid, and Houcine Ammar
Subjects: Chloroform, Absorption spectroscopy, Chemistry, Process Chemistry and Technology, General Chemical Engineering, Chromophore, Photochemistry, Fluorescence, Chloride, Catalysis, chemistry.chemical_compound, Yield (chemistry), medicine, Absorption (chemistry), medicine.drug
Abstract: A liquid/liquid interfacial technique was used to prepare biscoumarin dyes by condensing 7-hydroxy-4-methylcoumarin with various diacyl chlorides in the presence of a phase-transfer catalyst such as triethylbenzylammonium chloride. The reaction conditions were optimized. Six new biscoumarin derivatives were thus prepared in high yield. Their optical properties were studied in chloroform by UV/vis absorption and fluorescence spectroscopies. It appeared that the shape of the absorption spectra varies with the nature of the tether between both chromophores. In contrast, the excitation and emission spectra were almost unchanged, although the compounds exhibited drastic differences in their fluorescence efficiency.
Published: 2008

49. Preparation and optical properties of new fluorescent iminocoumarins: Study of N-acyl-derivatives

Author: Souhir Abid, Mehdi Fakhfakh, Suzanne Fery-Forgues, Rachid El Gharbi, and Hamida Turki
Subjects: Ethanol, Chemistry, General Chemical Engineering, Chemical structure, Substituent, General Physics and Astronomy, General Chemistry, Photochemistry, Medicinal chemistry, Fluorescence, Fluorescence spectroscopy, chemistry.chemical_compound, Group (periodic table), heterocyclic compounds, Absorption (chemistry)
Abstract: Six new iminocoumarin dyes, bearing a cyano group at the 3-position and a diethylamino group at the 7-position, were synthesized. These compounds differ by the nature of the acyl substituent borne by the imino group. They were studied in CH 2 Cl 2 and ethanol by UV/vis absorption and fluorescence spectroscopy. This work shows that the optical properties strongly depend on the nature of the substituent borne by the imino group, and indicates which type of substituent is favourable for a given application. It confirms that iminocoumarin derivatives could lead to a new generation of fluorescent probes, prone to easy modification of their chemical structure.
Published: 2007

50. Optical properties of new fluorescent iminocoumarins: Part 1

Author: Souhir Abid, Suzanne Fery-Forgues, Hamida Turki, and Rachid El Gharbi
Subjects: Group (periodic table), Chemistry, Process Chemistry and Technology, General Chemical Engineering, Quantum yield, Charge (physics), Emission spectrum, Absorption (chemistry), Photochemistry, Fluorescence, Fluorescence spectroscopy
Abstract: The optical properties of 10 new iminocoumarin dyes, bearing a cyano group at the 3-position, were studied in CH2Cl2 by UV/vis absorption and fluorescence spectroscopy. Five of the dyes bear a free imino group, and differ by the nature and position of their electron-donor group. Among them, the dye bearing a diethylamino group at the 7-position displayed the most interesting optical properties. All the compounds were compared to analogues containing an ethoxycarbonyl group on the imino function. The presence of the ethoxycarbonyl group systematically induced a shift of the absorption and emission spectra towards long wavelengths. For the three dyes where charge transfer is weak, substitution reduced fluorescence efficiency. In contrast, the fluorescence quantum yield and lifetime were slightly increased for the compounds with strong charge transfer, and especially for that bearing a diethylamino group at the 7-position. This shows that substitution on the imino group can be a convenient way to obtain good fluorescent probes designed for various purposes.
Published: 2007

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