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1. Engineering of ion permeable planar membranes and polymersomes based on β-cyclodextrin-cored star copolymers

Author

Haiqin Du, Sandra Kalem, Cécile Huin, Nicolas Illy, Guillaume Tresset, Fernando Carlos Giacomelli, and Philippe Guégan

Subjects
Biomaterials, Colloid and Surface Chemistry, Polymers, beta-Cyclodextrins, Molecular Conformation, Hydrophobic and Hydrophilic Interactions, Micelles, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials
Abstract

For polymersome-based nanoreactor purposes, we herein present the synthesis and characterization of well-defined star amphiphilic copolymers composed of a beta-cyclodextrin (βCD) core and seven poly(butylene oxide)-block-polyglycidol (PBO-PGL) arms per side (βCD-(PBO-PGL)

Published
2022

2. Bio-based poly(ester- alt -thioether)s synthesized by organo-catalyzed ring-opening copolymerizations of eugenol-based epoxides and N -acetyl homocysteine thiolactone

Author

Sylvain Caillol, Nicolas Illy, Philippe Guégan, Matthieu Bouzaid, Baptiste Quienne, Simon Le Luyer, Chimie des polymères (LCP), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)

Subjects
chemistry.chemical_classification, Vanillin, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Pollution, Aldehyde, 0104 chemical sciences, biobased polymers, chemistry.chemical_compound, Monomer, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Thioether, Polymerization, Benzyl alcohol, Polymer chemistry, Copolymer, Thiolactone, Environmental Chemistry, [CHIM]Chemical Sciences, 0210 nano-technology
Abstract

International audience; The anionic alternating ring-opening copolymerizations of three bio-based aromatic monomers, eugenol glycidyl ether (EGE), dihydroeugenol glycidyl ether (DEGE) and vanilin glycidyl ether (VGE), were carried out with renewable N-acetyl homocysteine thiolactone (NHTL) using benzyl alcohol and 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) as initiating system. This polymerization is a rare example of eugenol-based monomers used to synthesize linear polyesters. Alternating poly(ester-alt-thioether)s are obtained with number-average molar masses M n ranging from 1.1 to 10.8 kg mol-1 and dispersities as low as 1.20. The copolymer structures were carefully characterized by 1 H, 13 C, COSY, HSQC, 1 H-15 N NMR. It was found that the alternate copolymers were obtained selectively under different monomer feed ratios. In addition, the use of EGE and VGE monomers allows the preparation of multi-functional poly(ester-alt-thioether) respectively bearing allyl or aldehyde groups in each repeating unit. The copolymers display only clear glass transition temperatures higher than ambient temperature. This alternating copolymerization method offers a new chemical pathway for the valorization of bio-based aromatic compounds and expand the scope of renewable polyesters.

Published
2021

3. An alternative approach to create N-substituted cyclic dipeptides

Author

Nicolas Illy, Özgül Tezgel, Philippe Guégan, Sylvie Noinville, Véronique Bennevault, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), De la Molécule aux Nanos-objets : Réactivité, Interactions et Spectroscopies (MONARIS), Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Université d'Évry-Val-d'Essonne (UEVE), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), and ANR-17-CE18-0015,VINP,monopDNA-Nanoparticules Virus-Inspirées pour transfert de gènes.(2017)

Subjects
chemistry.chemical_classification, Polymers and Plastics, Peptidomimetic, Organic Chemistry, Bioengineering, Peptide, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, chemistry.chemical_compound, Monomer, chemistry, Polymerization, Nucleophile, [CHIM]Chemical Sciences, Lewis acids and bases, 0210 nano-technology, Isomerization, Phosphazene
Abstract

International audience; N-Modified peptide backbones are promising peptidomimetics which offer several advantages in terms of improved biological activity and stability. They further allow the development of novel functional materials. However, the synthesis of N-substituted peptides is very challenging with the existing methods, particularly the synthesis of peptides with larger N-substituents. In this work, we are introducing a new method to create N-polyether substituted cyclic dipeptides via anionic ring-opening polymerization (AROP). Four different cyclic dipeptides with different hydrophobic functional groups were selected to create N-substituted cyclic dipeptides. Backbone amides –NH– were deprotonated with phosphazene bases to form nucleophilic initiators. Furthermore, the effect of different phosphazene bases (tBuP4 and tBuP2) and of the addition of a Lewis acid (i-Bu3Al) was studied in detail towards creating N-polyether-cyclic dipeptides bearing either hydrophobic poly(butylene oxide) chains, or hydrophilic linear polyglycidol chains, thanks to the polymerization of 1,2-epoxybutane and the polymerization followed by the deprotection of t-butyl glycidyl ether monomers, respectively. Moreover, we have demonstrated the possibility of avoiding the isomerization of cyclic dipeptides during the synthesis of N-substituted analogues depending on the synthetic approach.

Published
2019

4. Alternating copolymerization of bio-based N-acetylhomocysteine thiolactone and epoxides

Author

Valentin Puchelle, Simon Le Luyer, Philippe Guégan, Nicolas Illy, Chimie des polymères (LCP), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Polymers and Plastics, Anionic ring-opening polymerization, General Physics and Astronomy, Epoxide, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Thioether, Polythioether, Alternating copolymerization, Polymer chemistry, Materials Chemistry, Copolymer, Moiety, Molar mass, Organic Chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Bio-based γ-thiolactone, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Polymerization, Benzyl alcohol, 0210 nano-technology, Glass transition
Abstract

International audience; The anionic ring-opening polymerizations (AROP) of bio-based N-acetyl homocysteine thiolactone (NHTL) and different epoxides were carried out using benzyl alcohol and 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) as initiating system. This polymerization is a rare example of AROP in the presence of an acidic moiety (acetamido group). Well-defined alternating poly(ester-alt-sulfide)s are obtained with number-average molar masses Mn ranging from 1.7 to 13.0 kg mol−1 and dispersities as low as 1.14. The presence of one acetamido function in the lateral group on each repeating unit of the copolymers derived from NHTL results in very significant increases (up to 94 °C) of the glass transition temperature Tg compared to similar poly(ester-alt-sulfide) derived from petro-based γ-butyrothiolactone (BTL). These functional poly(NHTL-alt-epoxide)s are valuable structures with numerous potential applications due to the presence in each repeating unit of one cleavable ester group and one redox-sensitive thioether group.

Published
2021

5. Functional Poly(ester- alt -sulfide)s Synthesized by Organo-Catalyzed Anionic Ring-Opening Alternating Copolymerization of Oxiranes and γ-Thiobutyrolactones

Author

Philippe Guégan, Laura Garnotel, Mathias Destarac, Mélanie Girardot, Léa Levesque, Valentin Puchelle, Yannick Latreyte, Olivier Coutelier, Nicolas Illy, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées, École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-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)-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), P3R - Polymères de Précision par Procédés Radicalaires (P3R), 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), Chimie des polymères (LCP), École normale supérieure - Paris (ENS Paris)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL (ENSCP)-ESPCI ParisTech-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS Paris)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL (ENSCP)-ESPCI ParisTech-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS Paris)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL (ENSCP)-ESPCI ParisTech-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS Paris)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL (ENSCP)-ESPCI ParisTech-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-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 National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Laboratoire Matériaux Polymères aux Interfaces (MPI), Université d'Évry-Val-d'Essonne (UEVE), Institut de Chimie et des Matériaux Paris-Est (ICMPE), Centre National de la Recherche Scientifique (CNRS)-Université Paris-Est Créteil Val-de-Marne - Paris 12 (UPEC UP12), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-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), 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-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)

Subjects
Polymers and Plastics, Sulfide, γthiobutyrolactone, Allyl glycidyl ether, polysulfide, 02 engineering and technology, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Catalysis, Inorganic Chemistry, epoxides, Reaction temperature, alternating copolymerization, Polymer chemistry, Materials Chemistry, Copolymer, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, Organic Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, Glycidyl ether, 0104 chemical sciences, chemistry, anionic ring-opening polymerization, 0210 nano-technology, Transesterification reaction
Abstract

The copolymerization of tert-butyl glycidyl ether (tBuGE), allyl glycidyl ether (AGE), ethoxyethyl glycidyl ether (EEGE) and 1,2-epoxybutane (BO) with γ-thiobutyrolactone was investigated using ben...

Published
2020

6. Temperature‐Sensitive Amphiphilic Non‐Ionic Triblock Copolymers for Enhanced In Vivo Skeletal Muscle Transfection

Author

Pierre Lehn, Philippe Guégan, Tristan Montier, Jérôme Mathe, Nicolas Illy, Bazoly Rasolonjatovo, Cécile Huin, Patrick Midoux, Bruno Pitard, Véronique Bennevault, Thomas Haudebourg, Tony Le Gall, Hervé Cheradame, Laboratoire Analyse, Modélisation et Matériaux pour la Biologie et l'Environnement (LAMBE - UMR 8587), Université d'Évry-Val-d'Essonne (UEVE)-Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-CY Cergy Paris Université (CY), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre de biophysique moléculaire (CBM), Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Génétique, génomique fonctionnelle et biotechnologies (UMR 1078) (GGB), EFS-Université de Brest (UBO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO), Host-Pathogen Interactions in the Regulation of Immune Responses (CRCINA-ÉQUIPE 5), Centre de Recherche en Cancérologie et Immunologie Nantes-Angers (CRCINA), Université d'Angers (UA)-Université de Nantes (UN)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre hospitalier universitaire de Nantes (CHU Nantes)-Université d'Angers (UA)-Université de Nantes (UN)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre hospitalier universitaire de Nantes (CHU Nantes), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO)-Université de Brest (UBO)-EFS-Institut National de la Santé et de la Recherche Médicale (INSERM), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Nantes - UFR de Médecine et des Techniques Médicales (UFR MEDECINE), Université de Nantes (UN)-Université de Nantes (UN)-Centre hospitalier universitaire de Nantes (CHU Nantes)-Centre National de la Recherche Scientifique (CNRS)-Université d'Angers (UA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Nantes - UFR de Médecine et des Techniques Médicales (UFR MEDECINE), Université de Nantes (UN)-Université de Nantes (UN)-Centre hospitalier universitaire de Nantes (CHU Nantes)-Centre National de la Recherche Scientifique (CNRS)-Université d'Angers (UA), and HAL-SU, Gestionnaire

Subjects
[CHIM.POLY] Chemical Sciences/Polymers, Phase transition, Polymers and Plastics, poly(2‐methyl‐2‐oxazoline), in vivo transfection, Bioengineering, 02 engineering and technology, Transfection, 010402 general chemistry, 01 natural sciences, Lower critical solution temperature, Biomaterials, Mice, In vivo, LCST, Amphiphile, Materials Chemistry, Copolymer, medicine, Animals, skeletal muscle, Muscle, Skeletal, Lipid bilayer, Chemistry, Skeletal muscle, DNA, 021001 nanoscience & nanotechnology, 0104 chemical sciences, medicine.anatomical_structure, [CHIM.POLY]Chemical Sciences/Polymers, Biophysics, amphiphilic copolymers, Female, 0210 nano-technology, Plasmids, Biotechnology
Abstract

International audience; It is reported that low concentration of amphiphilic triblock copolymers of pMeOx‐b‐pTHF‐b‐pMeOx structure (TBCPs) improves gene expression in skeletal muscle upon intramuscular co‐injection with plasmid DNA. Physicochemical studies carried out to understand the involved mechanism show that a phase transition of TBCPs under their unimer state is induced when the temperature is elevated from 25 to 37 °C, the body temperature. Several lines of evidences suggest that TBCP insertion in a lipid bilayer causes enough lipid bilayer destabilization and even pore formation, a phenomenon heightened during the phase transition of TBCPs. Interestingly, this property allows DNA translocation across the lipid bilayer model. Overall, the results indicate that TBCPs exhibiting a phase transition at the body temperature is promising to favor in vivo pDNA translocation in skeletal muscle cells for gene therapy applications.

Published
2020

7. Polymérisation de monomères époxide promue par la base phosphazène tBuP4 : une étude cinétique comparative

Author

Philippe Guégan, Nicolas Illy, Haiqin Du, Valentin Puchelle, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Polymers and Plastics, Allyl glycidyl ether, Organic Chemistry, Kinetics, Epoxide, Bioengineering, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Biochemistry, 0104 chemical sciences, chemistry.chemical_compound, Monomer, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Polymerization, Benzyl alcohol, Polymer chemistry, Reactivity (chemistry), Lewis acids and bases, 0210 nano-technology
Abstract

The kinetics of the anionic ring-opening polymerizations (AROP) of epoxide monomers, 1,2-epoxybutane (BO), 1,2-epoxypropane (PO), tert-butyl glycidyl ether (tBuGE), allyl glycidyl ether (AGE), benzyl glycidyl ether (BnGE), and ethoxyethyl glycidyl ether (EEGE), was investigated using benzyl alcohol/tBuP4 as the initiating system. All the polymerizations proceed in a controlled manner following a first order kinetics with respect to the monomer. The influence of the side chains borne by the oxirane ring was evidenced. Propagating centers derived from epoxide bearing heretoatom-containing side chains display higher reactivities and propagation rates. A reactivity scale has been established and is as follows, kp,BnGE > kp,AGE > kp,EEGE ≫ kp,tBuGE ≈ kp,PO > kp,BO. Using BO as the model monomer and different initiator concentrations, the nature of the propagating species has been identified as ion pairs. The influence of a Lewis acid addition on the monomer reactivities and on the control of the polymerization was also investigated. In the presence of triisobutylaluminum (iBu3Al), polymerization kinetics was faster but led to a broadening of the molar mass distributions. The monomer reactivity scale was also strongly modified with kp,PO > kp,BO > kp,EEGE ≈ kp,AGE > kp,BnGE ≈ kp,tBuGE. The polymerizations of PO, BO and tBuGE follow zero order kinetics which is not the case for the other oxirane monomers.

Published
2020

8. Phosphazene/triisobutylaluminum-promoted anionic ring-opening polymerization of 1,2-epoxybutane initiated by secondary carbamates

Author

Philippe Guégan, Nicolas Illy, L Hassouna, Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Polymers and Plastics, Bulk polymerization, Chemistry, Organic Chemistry, Bioengineering, Chain transfer, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Biochemistry, Ring-opening polymerization, 0104 chemical sciences, Deprotonation, Chain-growth polymerization, Polymerization, Polymer chemistry, [CHIM]Chemical Sciences, Molar mass distribution, 0210 nano-technology, Ionic polymerization
Abstract

International audience; Attempts to use a carbamate-phosphazene base as the initiating system for the polymerization of 1,2-epoxybutane was unsuccessful. As a matter of fact, carbamate deprotonation by phosphazene bases led to their fast decomposition generating alkoxide anions which initiate the polymerization rather than carbamate anions. Conversely, in the presence of triisobutylaluminum – a Lewis acid – the in situ generation of an anionic initiator X− obtained by the deprotonation of the tBuP4 phosphazene base was tested as a possible way to initiate the polymerization of 1,2-epoxybutane. Particular attention was given to the detection of eventual transfer or side-reactions according to the carbamate : triisobutylaluminum : phosphazene base ratio, to the solvent dielectric constant and to the number of P[double bond, length as m-dash]N– units in the phosphazene base. The reaction was performed with a stoichiometric ratio (1 : 1 : 1) of carbamate : triisobutylaluminum : tBuP2, which gave the best results. Under these conditions, the initiation of the polymerization by the carbamate anion was quantitative; no transfer reactions have been observed and the polymerization proceeded in a controlled manner to afford amide end-capped poly(butylene oxide) with a narrow molar mass distribution and expected molar masses.

Published
2017

9. pH‐Sensitive Poly(ethylene glycol)/Poly(ethoxyethyl glycidyl ether) Block Copolymers: Synthesis, Characterization, Encapsulation, and Delivery of a Hydrophobic Drug

Author

Michèle Salmain, Nicolas Illy, Philippe Guégan, Vincent Corcé, Vincent Molinié, Jéril Degrouard, Mélanie Labourel, Guillaume Tresset, Jeremy M. Zimbron, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Physique des Solides (LPS), and Centre National de la Recherche Scientifique (CNRS)-Université Paris-Sud - Paris 11 (UP11)

Subjects
Polymers and Plastics, curcumin encapsulation, 02 engineering and technology, amphiphilic polyether, 010402 general chemistry, 01 natural sciences, Micelle, chemistry.chemical_compound, Amphiphile, Polymer chemistry, Materials Chemistry, Copolymer, Physical and Theoretical Chemistry, Solubility, anionic-ring opening polymerization, Aqueous solution, Organic Chemistry, self-assembly, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 0104 chemical sciences, 3. Good health, [CHIM.POLY]Chemical Sciences/Polymers, [SDV.SP.PG]Life Sciences [q-bio]/Pharmaceutical sciences/Galenic pharmacology, chemistry, Polymerization, pH-sensitive copolymer, Curcumin, 0210 nano-technology, Ethylene glycol
Abstract

International audience; Curcumin is a natural polyphenolic compound known for its numerous pharmacological properties. However, its low water solubility and instability at neutral pH are serious drawbacks preventing its use as an oral drug. Well‐defined amphiphilic poly(ethylene glycol)‐block‐poly(ethoxyethyl glycidyl ether) (PEG‐b‐PEEGE) block copolymers carrying acid‐labile acetal groups are synthesized by anionic ring‐opening polymerization and investigated as potential pH‐sensitive nano‐carriers for delivery of curcumin to cancer cells. The nanoparticles, resulting from copolymer self‐assembly in aqueous media, are characterized by dynamic light scattering and cryo‐transmission electron microscopy. The nanoparticles’ stabilities are evaluated in three different phosphate buffers (pH = 7.2, 6.4, and 5.3). The stability decreases at lower pH and a complete disappearance of the nanoparticles is noticed after 4 days at pH 5.3. Curcumin is encapsulated in hydrophobic core of mPEG40‐b‐PEEGE25 nanoparticles allowing significant enhancements of curcumin solubility in water and lifetime at neutral pH. In vitro curcumin release is studied at different pH by UV‐spectroscopy and high‐performance liquid chromatography (HPLC). The cytotoxicity of curcumin and curcumin encapsulated in micelles is evaluated by cell viability 3‐(4,5‐Dimethyl‐2‐thiazolyl)‐2,5‐diphenyl‐2H‐tetrazolium bromide (MTT) assay on MDA‐MB‐231 human breast cancer cells

Published
2019

10. β-Cyclodextrin-Based Star Amphiphilic Copolymers: Synthesis, Characterization, and Evaluation as Artificial Channels

Author

Cécile Huin, Véronique Bennevault, Philippe Guégan, Nicolas Illy, Ibrahima Faye, Chimie des polymères (LCP), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Analyse et Modélisation pour la Biologie et l'Environnement (LAMBE), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université d'Évry-Val-d'Essonne (UEVE)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Saclay (COmUE), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, [PHYS]Physics [physics], Polymers and Plastics, Cyclodextrin, Organic Chemistry, 02 engineering and technology, Star (graph theory), 010402 general chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 01 natural sciences, 0104 chemical sciences, Characterization (materials science), Anionic addition polymerization, chemistry, Polymer chemistry, Materials Chemistry, [CHIM]Chemical Sciences, Physical and Theoretical Chemistry, 0210 nano-technology, Amphiphilic copolymer
Abstract

International audience; 14‐arm amphiphilic star copolymers are synthesized according to different strategies. First, the anionic ring polymerization of 1,2‐butylene oxide (BO) initiated by per(2‐O‐methyl‐3,6‐di‐O‐(3‐hydroxypropyl))‐β‐CD (β‐CD’OH14) and catalyzed by t‐BuP4 in DMF is investigated. Analyses by NMR and SEC show the well‐defined structure of the star β‐CD’‐PBO14. To obtain a 14‐arm poly(butylene oxide‐b‐ethylene oxide) star, a Huisgen cycloaddition between an α‐methoxy‐ω‐azidopoly(ethylene oxide) and the β‐CD’‐PBO14,whose end‐chains are beforehand alkyne‐functionalized, is performed. In parallel, 14‐arm star copolymers composed of butylene oxide‐b‐glycidol arms are successfully synthesized by the anionic polymerization of ethoxyethylglycidyl ether (EEGE) initiated by β‐CD’‐PBO14 with t‐BuP4. The deprotection of EEGE units is then performed to provide the polyglycidol blocks. These amphiphilic star polymers are evaluated as artificial channels in lipid bilayers. The effect of changing a PEO block by a polyglycidol block on the insertion properties of these artificial channels is discussed.

Published
2019

11. Synthesis and Solid-State Properties of PolyC3 (Co)polymers Containing (CH2−CH2−C(COOR)2) Repeat Units with Densely Packed Fluorocarbon Lateral Chains

Author

Sylvie Boileau, Alina V. Maryasevskaya, Denis V. Anokhin, Deogratias Urayeneza, Dimitri A. Ivanov, Blandine Brissault, Laurent Michely, Jacques Penelle, Nicolas Illy, Egor A. Bersenev, Penelle, Jacques, Chimie des polymères (LCP), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie et des Matériaux Paris-Est (ICMPE), Institut de Chimie du CNRS (INC)-Université Paris-Est Créteil Val-de-Marne - Paris 12 (UPEC UP12)-Centre National de la Recherche Scientifique (CNRS), Moscow Institute of Physics and Technology [Moscow] (MIPT), Lomonosov Moscow State University (MSU), Institut de Science des Matériaux de Mulhouse (IS2M), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), 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)-Institut de Chimie du CNRS (INC)-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)-Réseau nanophotonique et optique, 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)-Centre National de la Recherche Scientifique (CNRS), Kolmogorov, Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-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)-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 Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE)

Subjects
[CHIM.POLY] Chemical Sciences/Polymers, Materials science, Polymers and Plastics, chemistry.chemical_element, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Inorganic Chemistry, Differential scanning calorimetry, Materials Chemistry, Copolymer, Side chain, Fluorocarbon, semicrystalline and liquid crystalline polymers, chemistry.chemical_classification, Organic Chemistry, polymer synthesis, Fluorinated polymers, Polymer, 021001 nanoscience & nanotechnology, 3. Good health, 0104 chemical sciences, X-ray diffraction, self-associating side-chains in polymers, Crystallography, [CHIM.POLY]Chemical Sciences/Polymers, Polymerization, chemistry, X-ray crystallography, structure-property relationships in the solid-state, 0210 nano-technology, Carbon
Abstract

International audience; The synthesis and structural characterization of linear PolyC3 polymers containing trimethylene-1,1-dicarboxylate structural repeat units with C6F13 and C8F17 fluorinated side chains is described for the first time, and their properties were compared with the traditional polyvinyl structures thatdisplay the fluorinated chain on every second rather than on every third carbon alongside the backbone. Homopolymers as well as statistical and block copolymers with n-propyl and/or allyl trimethylene-1,1-dicarboxylate blocks have been obtained from PolyC3 precursors containing diallyl trimethylene-1,1-dicarboxylate units, by reacting C6F13−C2H4−SH and C8F17−C2H4−SH thiols with the allyl groups using a thiol−ene post- polymerization modification reaction. Solid-state properties have been investigated by differential scanning calorimetry for all of the (co)polymers and by small-angle X-ray scattering/wide-angle X-ray scattering for the C8F17 homopolymer at several temperatures. The structure of the homopolymer consistently shows a coexistence of two smectic phases at room temperature, which can be identified as SmB and SmC. This coexistence is assumed to arise from the fact that the distances between carboxylic oxygens bonded to the same carbon are very close to the ones between the neighboring carboxylic oxygens alongside the backbone, resulting in two possible ways of packing the pendant fluoroalkyl chains arranged in a hexatic order.

Published
2019

12. Modification of proline‐based 2,5‐diketopiperazines by anionic ring‐opening polymerization

Author

Philippe Guégan, Nicolas Illy, Haiqin Du, Özgül Tezgel, Valentin Puchelle, Chimie des polymères (LCP), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Polymers and Plastics, Chemistry, polyethers, Organic Chemistry, 02 engineering and technology, ring‐opening polymerization, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Ring-opening polymerization, 0104 chemical sciences, anionic polymerization, Anionic addition polymerization, [CHIM.POLY]Chemical Sciences/Polymers, Polymer chemistry, Materials Chemistry, peptides, Proline, 0210 nano-technology, Diketopiperazines
Abstract

International audience; 2,5‐Diketopiperazines (DKPs) are the smallest cyclic dipeptides found in nature with various attractive properties. In this study, we have demonstrated the successful modification of proline‐based DKPs using anionic ring‐opening polymerization (AROP) as a direct approach. Four different proline‐based DKPs with various side chains and increasing steric hindrance were used as initiating species for the polymerization of 1,2‐epoxybutane or ethoxyethyl glycidyl ether in the presence of t‐BuP4 phosphazene base. The addition of a Lewis acid, tri‐isobutyl aluminum, to the reaction mixture strongly decreased the occurrence of side reactions. Impact of the DKP side‐chain functionalities on molar mass control and dispersity was successfully evidenced.

Published
2019

13. Anionic ring-opening polymerization of N -glycidylphthalimide: Combination of phosphazene base and activated monomer mechanism

Author

Özgül Tezgel, Nicolas Illy, Philippe Guégan, Somasoudrame Rassou, Chimie des polymères (LCP), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut Parisien de Chimie Moléculaire (IPCM), and Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Polymers and Plastics, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Ring-opening polymerization, epoxy, Phthalimide, chemistry.chemical_compound, Polymer chemistry, Materials Chemistry, Lewis acids and bases, Ring Opening Polymerization, Molar mass, Anionic polymerization, living polymerization, Organic Chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Monomer, Anionic addition polymerization, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Polymerization, Living polymerization, 0210 nano-technology, Phosphazene bases
Abstract

International audience; Anionic ring‐opening polymerization of glycidyl phthalimide, initiated with alcohol–phosphazene base systems and based on monomer activation with a Lewis acid (iBu3Al), has been studied. No propagation occurred for initiator: iBu3Al ratios less or equal to 1:3. For larger Lewis acid amounts, the first anionic ring‐opening polymerizations of glycidyl phthalimide were observed. Polymers were carefully characterized by NMR, MALDI‐TOF mass spectrometry, and size exclusion chromatography and particular attention was given to the detection of eventual transfer or side‐reactions. However, polymer precipitation and transfer reaction to aluminum derivative were detrimental to monomer conversion, polymerization control, and limited polymer chain molar masses. The influence of reaction temperature and solvent on polymer precipitation and transfer reactions was studied and reaction conditions have been optimized leading to afford end‐capped poly(glycidyl phthalimide) with narrow molar mass distributions.

Published
2018

14. New prospects for the synthesis of N-alkyl phosphonate/phosphonic acid-bearing oligo-chitosan

Author

Ghislain David, Rémi Auvergne, Nicolas Illy, Bernard Boutevin, Guillaume Couture, Sylvain Caillol, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)

Subjects
Reaction conditions, chemistry.chemical_classification, General Chemical Engineering, technology, industry, and agriculture, macromolecular substances, General Chemistry, equipment and supplies, Phosphonate, carbohydrates (lipids), Chitosan, Hydrolysis, chemistry.chemical_compound, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Organic chemistry, ComputingMilieux_MISCELLANEOUS, Alkyl
Abstract

N-phosphonomethylation reactions of oligo-chitosan were performed according to Moedritzer and Kabachnik–Fields conditions. The different Moedritzer reaction conditions used did not allow the phosphonomethylation. On the contrary, the Kabachnik–Fields reactions led to oligo-chitosan methyl phosphonated derivatives. In addition, novel dialkyl phosphoryl oligo-chitosan was synthesized in water at room temperature via epoxy–amine reactions of oligo-chitosan with dialkyl (3-(oxiran-2-ylmethoxy)propyl) phosphonates. This simple and efficient synthetic method provides a new approach for the preparation of phosphonated oligo-chitosan derivatives. Then, the hydrolysis of the phosphonated compounds to generate the phosphonic acid moieties was investigated. The mildest conditions were determined in order to avoid the chitosan backbone degradation. All the products were characterized by 1H and 31P NMR analyses.

Published
2014

15. Correction: A polymeric membrane permeabilizer displaying densely packed arrays of crown ether lateral substituents

Author

Valessa Barbier, Karol Ondrias, Blandine Brissault, Nicolas Illy, Anna Bertova, Ming Liu, Jacques Penelle, Institut de Chimie et des Matériaux Paris-Est (ICMPE), Institut de Chimie du CNRS (INC)-Université Paris-Est Créteil Val-de-Marne - Paris 12 (UPEC UP12)-Centre National de la Recherche Scientifique (CNRS), and Institute of Molecular Physiology and Genetics, Slovak Academy of Sciences

Subjects
chemistry.chemical_classification, General Chemical Engineering, Potassium, chemistry.chemical_element, 02 engineering and technology, General Chemistry, Polymer, [CHIM.MATE]Chemical Sciences/Material chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, [SDV.BBM.BP]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biophysics, stomatognathic diseases, Membrane, [CHIM.POLY]Chemical Sciences/Polymers, stomatognathic system, chemistry, Polymer chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Polymeric membrane, 0210 nano-technology, Carbon, Crown ether, Macromolecule
Abstract

We report the design, synthesis and evaluation of a novel macromolecular membrane permeabilizer displaying geminally substituted crown-ethers (18-crown-6) on every third carbon alongside the backbone. The polymer has a rather high affinity with potassium as well as permeabilization properties towards K+, Na+ and Ca2+, including single-channel behavior.

Published
2016

16. A polymeric membrane permeabilizer displaying densely packed arrays of crown ether lateral substituents

Author

Ming Liu, Anna Bertova, Nicolas Illy, Blandine Brissault, Jacques Penelle, Karol Ondrias, Valessa Barbier, Institute of Molecular Physiology and Genetics, Slovak Academy of Sciences, Institut de Chimie et des Matériaux Paris-Est (ICMPE), and Université Paris-Est Créteil Val-de-Marne - Paris 12 (UPEC UP12)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[SDV.BBM.BP]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biophysics, [CHIM.POLY]Chemical Sciences/Polymers, 010405 organic chemistry, General Chemical Engineering, [CHIM.COOR]Chemical Sciences/Coordination chemistry, General Chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences
Abstract

Correction available: Liu, M.; Bertova, A.; Illy, N.; Brissault, B.; Penelle, J.; Ondrias, K.; Barbier, V. “Correction - A Polymeric Membrane Permeabilizer Displaying Densely Packed Arrays of Crown Ether Lateral Substituents”, RSC Advances, 2016, 6, 14222 (DOI: 10.1039/C6RA90009g).; International audience; We report the design, synthesis and evaluation of a novel macromolecular membrane permeabilizer displaying geminally substituted crown-ethers (18-crown-6) on every third carbon alongside the backbone. The polymer has a rather high affinity with potassium as well as permeabilization properties towards K+, Na+ and Ca2+, including single-channel behavior.

Published
2012

17. Phosphorylation of bio-based compounds: the state of the art

Author

Maxence Fache, Raphaël Ménard, Claire Negrell, Sylvain Caillol, Ghislain David, Nicolas Illy, Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Green chemistry, chemistry.chemical_classification, Cardanol, Polymers and Plastics, business.industry, Organic Chemistry, Bio based, chemistry.chemical_element, Bioengineering, Polymer, 7. Clean energy, Biochemistry, 12. Responsible consumption, Renewable energy, chemistry.chemical_compound, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, 13. Climate action, Organic chemistry, Cellulose, business, Carbon, Renewable resource
Abstract

International audience; Over the last few years, more and more papers have been devoted to phosphorus-containing polymers, mainly due to their fire resistance, excellent chelating and metal-adhesion properties. Nevertheless, sustainability, reduction of environmental impacts and green chemistry are increasingly guiding the development of the next generation of materials. The use of bio-based polymer matrices might allow the reduction of environmental impacts by using renewable carbon and by achieving more easily biodegradable or reusable materials. The aim of this review is to present both fundamental and applied research on the phosphorylation of renewable resources, through reactions on naturally occurring functions, and their use in biobased polymer chemistry and applications. In the first section, different strategies for the introduction of phosphorus-containing functions on organic backbones are described. In the following sections, the main families of chemicals based on renewable resources are covered: namely polysaccharides (cellulose, chitosan, starch, dextran etc.), biophenols (lignins, biobased phenolic compounds, cardanol etc.), triglycerides (oils, glycerol) and hydroxy acid compounds.

Published
2015

18. Synthesis and anionic ring-opening polymerization of crown-ether-like macrocyclic dilactones: An alternative route to PEG-containing polyesters and related networks

Author

Ediz Taylan, Jacques Penelle, Valessa Barbier, Sylvie Boileau, Blandine Brissault, Justyna Wojno, Nicolas Illy, Institut de Chimie et des Matériaux Paris-Est (ICMPE), Institut de Chimie du CNRS (INC)-Université Paris-Est Créteil Val-de-Marne - Paris 12 (UPEC UP12)-Centre National de la Recherche Scientifique (CNRS), Boğaziçi University [Istanbul], Université Paris-Est Créteil Val-de-Marne - Paris 12 (UPEC UP12)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Boǧaziçi üniversitesi = Boğaziçi University [Istanbul]

Subjects
Materials science, Polymers and Plastics, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, General Physics and Astronomy, Solution polymerization, 02 engineering and technology, Polyethylene glycol, [CHIM.MATE]Chemical Sciences/Material chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Ring-opening polymerization, 0104 chemical sciences, Polyester, chemistry.chemical_compound, Anionic addition polymerization, Chain-growth polymerization, [CHIM.POLY]Chemical Sciences/Polymers, Polymerization, chemistry, Polymer chemistry, Materials Chemistry, 0210 nano-technology, Ionic polymerization
Abstract

International audience; Linear aliphatic polyesters whose structure is made of short polyethylene glycol (PEG) segments connected along the chain by malonate units were synthesized from two PEG- containing macrolactones: 15,15-dimethyl-1,4,7,10,13-pentaoxacyclohexadecane-14, 16-dione (1) and 5,8,11,14,17-pentaoxaspiro[2,15]octadecane-4,18-dione (2). Anionic ring-opening polymerization conditions using either thiophenolates or a p-nitrophenolate as initiators yielded poly(ether-ester)s of low to moderate molecular weights, with broad molecular weight distributions. When the monomer also contains an activated cyclopro- pane unit of the cyclopropane-1,1-dicarboxylate type (such as in 2) and harsher polymer- ization conditions are used (higher temperatures and bulkier counterions), opening of the cyclopropyl ring can compete with the dilactone polymerization, providing access to cross- linked materials.

Published
2013

19. Correction: Phosphorylation of bio-based compounds: the state of the art

Author

Sylvain Caillol, Claire Negrell, Raphaël Ménard, Maxence Fache, Ghislain David, and Nicolas Illy

Subjects
Polymers and Plastics, Polymer science, Computational chemistry, Chemistry, Organic Chemistry, Phosphorylation, Bio based, Bioengineering, Biochemistry
Abstract

Correction for ‘Phosphorylation of bio-based compounds: the state of the art’ by Nicolas Illy, et al., Polym. Chem., 2015, 6, 6257–6291.

Published
2016

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