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1. Luminescent imidazolium–naphthalene salts in liquid and solid states

Author

Emilie Bordes, Julien Fouchet, Nicolas Del-Giudice, Matthieu L’Her, Laurent Douce, Youssef Atoini, Lydia Karmazin, Loïc Charbonière, Benoît Heinrich, Luisa De Cola, Emma Scrafton, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace, Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Université de Strasbourg (UNISTRA), Institut de Science et d'ingénierie supramoléculaires (ISIS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace, Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Université de Strasbourg (UNISTRA)-Réseau nanophotonique et optique, Institut de Chimie de Clermont-Ferrand (ICCF), Centre National de la Recherche Scientifique (CNRS)-Université Clermont Auvergne [2017-2020] (UCA [2017-2020])-SIGMA Clermont (SIGMA Clermont), Institut Pluridisciplinaire Hubert Curien (IPHC), Université de Strasbourg (UNISTRA)-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Ionic bonding, 02 engineering and technology, Conjugated system, 010402 general chemistry, Photochemistry, 01 natural sciences, Catalysis, symbols.namesake, chemistry.chemical_compound, Materials Chemistry, [CHIM]Chemical Sciences, Moiety, ComputingMilieux_MISCELLANEOUS, Alkyl, Naphthalene, chemistry.chemical_classification, [CHIM.ORGA]Chemical Sciences/Organic chemistry, General Chemistry, Chromophore, 021001 nanoscience & nanotechnology, 0104 chemical sciences, chemistry, symbols, van der Waals force, 0210 nano-technology, Luminescence
Abstract

International audience; This article describes highly luminescent ionic compounds in liquid and crystalline states, where a naphthalene moiety is conjugated to an imidazolium center decorated with alkyl chains of different lengths. We have characterized, by X-ray diffraction of a single crystal and the liquid, that these compounds are organized in rod-shaped assemblies. The formation of this molecular architecture is governed by ionic interactions that dominate those of the lesser π–π and van der Waals interactions. Consequently, aromatic naphthalene rings are confined to the environment of alkyl chains (diluted in an apolar solvent), thus avoiding the extinction of luminescence by the formation of chromophore excimers, as shown in photophysical data.

Published
2019
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2. Heterogeneous microwave-assisted Ullmann type methodology for synthesis of rigid-core ionic liquid crystals

Author

Lydia Karmazin, Richard Welter, Arsalan Mirjafari, Emilie Voirin, Julien Fouchet, Laurent Douce, Corinne Bailly, Benoît Heinrich, Matthieu L’Her, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de biologie moléculaire des plantes (IBMP), Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), and Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
010405 organic chemistry, Small-angle X-ray scattering, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, 010402 general chemistry, 01 natural sciences, Catalysis, Coupling reaction, 0104 chemical sciences, chemistry.chemical_compound, Differential scanning calorimetry, chemistry, Bromide, Yield (chemistry), Ionic liquid, Materials Chemistry, Physical chemistry, Lamellar structure, Methyl group
Abstract

We present an efficient Ullmann-type synthesis methodology enabling the preparation of imidazolium compounds with an extended aromatic core in three steps. This procedure begins with a microwave-assisted, heterogeneously catalysed cross-coupling reaction in the presence of Cu(II)-doped NaY zeolite to obtain imidazole-aromatic derivatives directly in good yield. The innovation is that this reaction does not require solvent, ligand or an inert atmosphere. Subsequently, these derivatives have been alkylated with bromoalkanes and the bromide of the imidazolium products exchanged for [BF4]− or [PF6]− anions. We have studied the influence of the methyl group (inductive effect) on the aromatic unit during the coupling reaction as well as its impact on different arrangements in the crystalline state. We have been able to extend this synthesis to ionic liquid crystal compounds which display lamellar self-organization (smectic A). The mesomorphic behavior and phase transition temperatures were investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and small-angle X-ray scattering (SAXS).

Published
2018
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3. Correction: Luminescent imidazolium–naphthalene salts in liquid and solid states

Author

Youssef Atoini, Loïc J. Charbonnière, Emilie Bordes, Benoît Heinrich, Luisa De Cola, Matthieu L’Her, Emma Scrafton, Lydia Karmazin, Nicolas Del-Giudice, Laurent Douce, and Julien Fouchet

Subjects
Chemistry, Inorganic chemistry, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, Materials Chemistry, 0210 nano-technology, Luminescence, Naphthalene
Abstract

Correction for ‘Luminescent imidazolium–naphthalene salts in liquid and solid states’ by Matthieu L’Her et al., New J. Chem., 2019, 43, 12529–12532.

Published
2020
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4. Liquid Crystal Imidazolium Salts: Towards Materials for Catalysis and Molecular Electronics

Author

Laurent Douce, Richard Welter, Miyake Yasuo, Jean-Moïse Suisse, Aline Maisse-François, Yo Shimizu, and Stéphane Bellemin-Laponnaz

Subjects
chemistry.chemical_classification, Inorganic chemistry, Mesophase, 02 engineering and technology, Crystal structure, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, Catalysis, Inorganic Chemistry, chemistry.chemical_compound, Crystallography, Differential scanning calorimetry, chemistry, Liquid crystal, Lamellar structure, 0210 nano-technology, Carbene, Alkyl
Abstract

1,3-Bis(4-alkyloxyphenyl)-3H-imidazol-1-ium trifluoromethanesulfonates, alkyl = CH3(CH2)n–1, n = 8, 10, 12, 14 and 16, can be derived from the analogous 4-alkyloxyphenylamines. These imidazolium salts exhibit a lamellar liquid-crystal mesophase between 99 °C and 191 °C. The smectic-A phase was fully characterised by polarising optical microscopy, differential scanning calorimetry and X-ray diffraction. We report also the synthesis, lamellar crystal structure and catalytic activity of the PdII complex of the (deprotonated) carbene form of one of these salts. In addition, we measured the charged carrier mobilities in the mesophase.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Published
2007
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5. Phosphine oxide functionalised with two bipyridine subunits: a novel ligand for the engineering of sterically hindered complexes

Author

Michèle Cesario, Loïc J. Charbonnière, Raymond Ziessel, and Laurent Douce

Subjects
Steric effects, Phosphine oxide, Chemistry, Stereochemistry, Ligand, chemistry.chemical_element, General Chemistry, Copper, Catalysis, Crystallography, chemistry.chemical_compound, Bipyridine, Absorption band, Materials Chemistry, Molecule, Titration
Abstract

Ligand L, containing two 6-methyl-6′-methyl-yl-2,2′-bipyridine moieties linked by a “PhPO” spacer, has been prepared. Subsequent complexation with [Cu(CH3CN)4](BF4) led to a unique complex of formula [CuL](BF4). The molecular structure has been determined by X-ray crystallography in the solid state and NMR studies in solution. The complex displays an intense absorption band in the visible wavelength range with maxima at 418 and 509 nm, and is oxidised reversibly at +0.66 V (ΔEp = 80 mV) to the corresponding Cu(II) species, while two successive reductions of the coordinated bipyridine fragments occur at −1.60 (ΔEp = 66) and −1.84 V (ΔEp = 70 mV) s. SCE. Direct spectrophotometric titrations with global analysis allowed us to elicit stability constants for the emergent complex and to highlight the formation of a dinuclear complex in the presence of excess copper.

Published
2001
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7. First assembly of copper(I) naphthyridine-based helicates

Author

Laurent Douce, Alain Van Dorsselaer, He´lène Nierengarten, Raymond Ziessel, Abdelkrim El-Ghayoury, Anthony Harriman, and Emmanuelle Leize

Subjects
Chemistry, Stereochemistry, Polymer chemistry, Materials Chemistry, chemistry.chemical_element, Titration, General Chemistry, Electrospray ms, Copper, Catalysis
Abstract

Copper(I) binds to 2,7-diimino-1,8-naphthyridine in solution to form a mixture of equilibrating mono- and polynuclear complexes, as identified by electrospray MS and monitored by UV-visible spectrophotometric titrations, including a binuclear metallo-helicate for which X-ray data are available but whose formation does not require cooperative associations.

Published
2000
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8. π-Stackedortho-Palladated Bipyridine Complexes Exhibiting Unusual Liquid Crystalline Behavior

Author

Abdelkrim El-Ghayoury, Raymond Ziessel, Laurent Douce, and Antoine Skoulios

Subjects
chemistry.chemical_classification, Materials science, Morphology (linguistics), Liquid crystalline, Salt (chemistry), chemistry.chemical_element, General Chemistry, Photochemistry, Catalysis, Bipyridine, chemistry.chemical_compound, Crystallography, chemistry, Lamellar structure, Palladium
Abstract

A columnar structure with lamellar morphology in the liquid crystalline state is displayed by the palladium complex salt 1, which is synthesized from nonmesogenic ligands.

Published
1998
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9. Electrodeposition of silver particles and gold nanoparticles from ionic liquid-crystal precursors

Author

Jean-Moïse Suisse, William Dobbs, Richard Welter, Laurent Douce, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), and Masson, Beatrice

Subjects
Electrolysis, Materials science, Aqueous solution, 010405 organic chemistry, Inorganic chemistry, General Medicine, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Catalysis, 0104 chemical sciences, law.invention, Crystal, chemistry.chemical_compound, chemistry, law, Liquid crystal, Colloidal gold, Yield (chemistry), Ionic liquid, Particle size, 0210 nano-technology
Abstract

Wenowpresentastrategyforamoreversatileexploita-tionofliquid-crystaltemplateeffects,whichisillustratedbythe electrolysis of imidazolium liquid crystals containingdicyanoargentate(I)anddicyanoaurate(I)anionstoproducesilverandgoldnanoparticles.Thekeytothisapproachisthecouplingoftheself-organizationoftheimidazoliummetallatetotheuseofelectrochemicalreduction,thelatterprovidingthe means to control the particle size and form of theelectrodeposited metals by variation of parameters such asthepotentialandthecurrentdensity.Many mesomorphic imidazolium salts can be readilypreparedbysimplemetathesisreactionsinvolvingprecipita-tion from aqueous solutions containing the appropriateanions. In investigating this chemistry, we sought to useanionsincorporatingtransitionmetalstoendowtheproductswith properties such as redox activity and variable conduc-tivity.Thus,wehavesynthesizeddicyanoargentate(I)(1)anddicyanoaurate(I)(2)derivativesof3-(4-dodecyloxybenzyl)-1-methyl-1H-imidazolium in good yield(over 80%) from thebromidestartingmaterial(Scheme1).

Published
2006

10. New ionic liquid crystals based on imidazolium salts

Author

Alain Louati, William Dobbs, Laurent Douce, Lionel Allouche, François Malbosc, Richard Welter, Institut de Physique et Chimie des Matériaux de Strasbourg (IPCMS), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Strasbourg, Centre National de la Recherche Scientifique (CNRS)-Université Louis Pasteur - Strasbourg I-Institut de Chimie du CNRS (INC), Laboratoire de Chimie Quantique, Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de biologie moléculaire des plantes (IBMP), Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), and Masson, Beatrice

Subjects
Inorganic chemistry, 02 engineering and technology, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, Electrochemistry, Metathesis, 01 natural sciences, Catalysis, 0104 chemical sciences, Ion, Crystal, chemistry.chemical_compound, chemistry, Bromide, Ionic liquid, Materials Chemistry, 0210 nano-technology
Abstract

The new ionic liquid crystal 1-(4-dodecyloxybenzyl)-3-methyl-1H-imidazol-3-ium bromide has been synthesized and its X-ray structure obtained; various salts containing BF4−, SCN−, PF6−, CF3SO3−, (CF3SO2)2N− have been prepared by anion metathesis in water from bromide species as starting materials, and finally, the mesomorphism and electrochemical behavior have been investigated.

Published
2006
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11. A luminescent anion sensor based on a europium hybrid complex

Author

Luca Prodi, Raymond Ziessel, Loïc J. Charbonnière, Marco Montalti, Laurent Douce, and Nelsi Zaccheroni

Subjects
Anions, Luminescent Measurements, Spectrophotometry, Infrared, Kinetics, Inorganic chemistry, chemistry.chemical_element, General Chemistry, Biochemistry, Catalysis, Ion, Colloid and Surface Chemistry, chemistry, Europium, Organometallic Compounds, Spectrophotometry, Ultraviolet, Luminescence, Group 2 organometallic chemistry
Published
2001

12. Mesomorphic phenanthroline derivatives: novel architectures based on hydrogen bondingElectronic supplementary information (ESI) available: FT-IR spectra of compounds L12 and 1′16 and X-ray diffraction pattern of the palladium complex of L16. See http://www.rsc.org/suppdata/cc/b1/b110239g

Author

Laurent Douce, Guillaume Pickaert, Daniel Guillon, and Raymond Ziessel

Subjects
Chemistry, Hydrogen bond, Phenanthroline, Metals and Alloys, chemistry.chemical_element, General Chemistry, Photochemistry, Catalysis, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, chemistry.chemical_compound, Polymer chemistry, Materials Chemistry, Ceramics and Composites, Palladium
Abstract

Strong hydrogen bonding has been observed in mesomorphic phenanthroline compounds engineered from diacylaminobenzene platforms: a columnar organization is found in the free ligands (n = 12 or 16) whereas a smectic arrangement is evidenced in a palladium complex (n = 16).

Published
2002
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13. Synthesis and coordinative properties of a hybrid bis(diphenylphosphino)methane–terpyridine

Author

Michèle Cesario, Laurent Douce, Guillaume Pickaert, and Raymond Ziessel

Subjects
Stereochemistry, Ligand, Metals and Alloys, General Chemistry, Catalysis, Methane, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, chemistry.chemical_compound, Deprotonation, chemistry, Polymer chemistry, Materials Chemistry, Ceramics and Composites, Terpyridine
Abstract

A newly-synthesized 4′-[bis(diphenylphosphino)methane]–2,2′∶6′,2 ″-terpyridine-based (dppm–terpy) ligand forms complexes by selective complexation of the terpy or diphos segment, respectively, with Fe(II) or Pd(II) salts; in the latter case, an X-ray structural analysis reveals the formation of a neutral square-planar complex assembled from the deprotonated ligands.

Published
2000
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14. Columnar mesophases from tetrahedral copper(I) cores and Schiff-base derived polycatenar ligands

Author

Laurent Douce, Abdelkrim El-Ghayoury, Raymond Ziessel, and Antoine Skoulios

Subjects
Schiff base, Inorganic chemistry, Metals and Alloys, chemistry.chemical_element, General Chemistry, Metallomesogen, Copper, Catalysis, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Metal, chemistry.chemical_compound, chemistry, visual_art, Polymer chemistry, Materials Chemistry, Ceramics and Composites, visual_art.visual_art_medium, Tetrahedron
Abstract

In the presence of copper(I), certain di- and tri-topic ligands derived from reaction of substituted anilines with 2-pyridinecarbaldehyde or 2,6-pyridinedicarbaldehyde form a new type of polycatenar metallomesogen around the tetrahedral metallic centre.

Published
1999
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