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9. Photo-induced ring-opening polymerization of trimethylene carbonate-based liquid resins: Towards biodegradable patterned coatings

Author

Zivic, Nicolas, primary, Brossier, Thomas, additional, Crestey, Floriane, additional, Catrouillet, Sylvain, additional, Chemtob, Abraham, additional, Héroguez, Valérie, additional, Lacroix-Desmazes, Patrick, additional, Joly-Duhamel, Christine, additional, Blanquer, Sébastien, additional, and Pinaud, Julien, additional

Published
2022
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10. Thermal Degradation of Fluorosilicone Elastomers

Author

Richaud, Emmanuel, primary, Pires, Leticia, additional, Roland, Sébastien, additional, Truffault, Laurianne, additional, Laiarinandrasana, Lucien, additional, Corfa, Alice, additional, Pinaud, Julien, additional, Caillol, Sylvain, additional, Ladmiral, Vincent, additional, and Beauvais, Christophe, additional

Published
2022
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11. Lignin-based bisguaiacol diisocyanate: a green route for the synthesis of biobased polyurethanes.

Author

Lemouzy, Sébastien, Delavarde, Aliénor, Lamaty, Frédéric, Bantreil, Xavier, Pinaud, Julien, and Caillol, Sylvain

Subjects
ISOCYANATES, LIGNOCELLULOSE, POLYURETHANES, METHYLENE diphenyl diisocyanate, AROMATIC amines, POLYMERIZATION
Abstract

The synthesis of a new biobased aromatic diisocyanate derived from lignocellulosic raw material, namely guaiacol and vanillyl alcohol, through phosgene-free route offers the prospect of greener approaches for isocyanate production and the polyurethane industry. Indeed, bisguaiacol F diisocyanate (BGI) was obtained via a three-step process from readily available bisguaiacol F (BGF), involving conversion of aromatic amine into aromatic isocyanate. The unusual transition-metal-free conversion of BGF to bisguaiacol F diamine (BGA) was performed by a two-step approach: (a) the Williamson-type alkylation of BGF and then (b) the base-promoted Smiles rearrangement of bis O-alkylated BGF. In order to improve the sustainability of this process, the first step was realized under solvent-free mechanochemical conditions, and the second step was performed using two different activating methods: thermal and microwave. The thermal process provided an isolated BGA yield of ca. 70%. Microwave activation proved to be an interesting alternative, although a lower yield (32%) of the desired BGA was achieved. Finally, the diisocyanate synthesis was performed via a phosgene-free/room temperature protocol using di-tert-butyl dicarbonate in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP). Two polyurethane thermosets were designed and synthesized using the aromatic diisocyanates, biobased BGI and petrochemical-based methylene diphenyl diisocyanate (MDI), by a solvent-free two-step polymerization. Their thermo-chemical properties as well as their reactivities for polymer synthesis were evaluated. These preliminary results suggest that BGI could be potentially used as a nearly fully biobased surrogate for MDI. [ABSTRACT FROM AUTHOR]

Published
2023
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15. Non‐Covalent Polymer Surface Modification of Cellulose Nanocrystals Using Block Copolymers

Author

Torres-Rocha, Olga Lidia, Campbell, Sophie, Woodcock, Nicole, Pinaud, Julien, Lacroix-Desmazes, Patrick, Champagne, Pascale, Cunningham, Michael, 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), Department of Chemical Engineering, Queen's University, Queen's University, Queen's University [Kingston, Canada], and Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-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
Polymers and Plastics, nitroxide me-diated polymerization, General Chemical Engineering, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, block copolymers, graft modification, [CHIM]Chemical Sciences, 0210 nano-technology, cellulose nanocrystals, ComputingMilieux_MISCELLANEOUS
Abstract

International audience; Cellulose nanocrystals (CNC) possess desirable mechanical and opticalproperties that make them a candidate in the development of the nextgeneration of polymer-based composites. However, CNC also have a criticalissue associated with their use: their hydrophilicity and incompatibility withhydrophobic polymers. CNC surface properties must be modified for them tobe successfully implemented by the industrial sector. Grafting (co)polymerschains on the CNC surface can provide compatibility to CNC withhydrophobic matrices and expand their potential range of applications. In thiscommunication preliminary results of a simple method to functionalize CNCsurface are reported using block copolymers, where a cationic block anchorsvia complexation to the anionically charged CNC surface and the other blockacts as a stabilizing block, providing dispersibility in various solvents. This is amuch simpler and less expensive method than current routes based oncovalent modification. The block copolymers poly(polyethylene glycolmethacrylate)-b-poly(N-butyl-N′-vinyl imidazolium bromide)(PPEGMA-b-PBuVIm) and poly(styrene)-b-PBuVIm (PS-b-PBuVIm) are firstsynthesized via nitroxide-mediated polymerization and then non-covalentlyadsorbed on the CNC surface. The functionalization has been confirmed viaFT-IR and TGA. The dispersion of polymer-modified CNC materials in organicsolvents is evaluated via dynamic light scattering. Modified CNC yieldedstable dispersions in organic solvents.

Published
2021

17. Enhanced aminolysis of cyclic carbonates by β-hydroxyamines for fully biobased polyhydroxyurethanes

Author

Quienne, Baptiste, Poli, Rinaldo, Pinaud, Julien, Caillol, Sylvain, 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), Laboratoire de chimie de coordination (LCC), 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-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)-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 Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), 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), 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), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)

Subjects
reactivity, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, cyclic carbonate, [CHIM.POLY]Chemical Sciences/Polymers, polyhydroxyurethanes, β-hydroxyamines, DFT, biobased polymers
Abstract

International audience; The aminolysis of five-membered cyclic carbonates which results in polyhydroxyurethanes (PHUs) is one of the most promising synthetic pathway to achieve isocyanate-free polyurethanes (NIPUs), one of the main industrial challenges over the coming years. This study highlighted the higher reactivity of β-hydroxyamines toward cyclic carbonate in comparison to classical alkylamines through the determination of their reaction rate constants. The key role of the β-OH substituent in the aminolysis was enlighten by a DFT investigation. Polyfunctional alkylamine and β-hydroxyamine were then used for the synthesis of fully biobased PHU thermosets. The higher reactivity of β-hydroxyamines was confirmed by the gelation time gap between the two formulations studied. After curing, the thermal and thermo-mechanical properties of the thermosets were compared.

Published
2021

20. Non‐Covalent Polymer Surface Modification of Cellulose Nanocrystals Using Block Copolymers.

Author

Torres‐Rocha, Olga Lidia, Campbell, Sophie, Woodcock, Nicole, Pinaud, Julien, Lacroix‐Desmazes, Patrick, Champagne, Pascale, and Cunningham, Michael F.

Subjects
CELLULOSE nanocrystals, POLYMERS, POLYETHYLENE glycol, LIGHT scattering, SURFACE properties, ORGANIC solvents, BLOCK copolymers
Abstract

Cellulose nanocrystals (CNC) possess desirable mechanical and optical properties that make them a candidate in the development of the next generation of polymer‐based composites. However, CNC also have a critical issue associated with their use: their hydrophilicity and incompatibility with hydrophobic polymers. CNC surface properties must be modified for them to be successfully implemented by the industrial sector. Grafting (co)polymers chains on the CNC surface can provide compatibility to CNC with hydrophobic matrices and expand their potential range of applications. In this communication preliminary results of a simple method to functionalize CNC surface are reported using block copolymers, where a cationic block anchors via complexation to the anionically charged CNC surface and the other block acts as a stabilizing block, providing dispersibility in various solvents. This is a much simpler and less expensive method than current routes based on covalent modification. The block copolymers poly(polyethylene glycol methacrylate)‐b‐poly(N‐butyl‐N′‐vinyl imidazolium bromide) (PPEGMA‐b‐PBuVIm) and poly(styrene)‐b‐PBuVIm (PS‐b‐PBuVIm) are first synthesized via nitroxide‐mediated polymerization and then non‐covalently adsorbed on the CNC surface. The functionalization has been confirmed via FT‐IR and TGA. The dispersion of polymer‐modified CNC materials in organic solvents is evaluated via dynamic light scattering. Modified CNC yielded stable dispersions in organic solvents. [ABSTRACT FROM AUTHOR]

Published
2022
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28. Micellisation électrostatique de copolymères à blocs double-hydrophiles

Author

PHIMPHACHANH, Anthony, Lacroix-Desmazes, Patrick, Pinaud, Julien, harrisson, simon, Destarac, Mathias, IN, Martin, Gerardin, Corine, Laboratoire Charles Coulomb (L2C), Université de Montpellier (UM)-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 Galien Paris-Sud (IGPS), Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), 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
[CHIM.POLY]Chemical Sciences/Polymers, [PHYS.COND.CM-SCM]Physics [physics]/Condensed Matter [cond-mat]/Soft Condensed Matter [cond-mat.soft], ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

29. Mixture of Azolium Tetraphenylborate with Isopropylthioxanthone: A New Class of N‐Heterocyclic Carbene (NHC) Photogenerator for Polyurethane, Polyester, and ROMP Polymers Synthesis

Author

Trinh, Thi Kim Hoang, primary, Malval, Jean‐Pierre, additional, Morlet‐Savary, Fabrice, additional, Pinaud, Julien, additional, Lacroix‐Desmazes, Patrick, additional, Reibel, Corine, additional, Héroguez, Valérie, additional, and Chemtob, Abraham, additional

Published
2019
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31. Photoreduction of triplet thioxanthone derivative by azolium tetraphenylborate: a way to photogenerate N-heterocyclic carbenes

Author

Trinh, Thi Kim Hoang, primary, Morlet-Savary, Fabrice, additional, Pinaud, Julien, additional, Lacroix-Desmazes, Patrick, additional, Reibel, Corine, additional, Joyeux, Cécile, additional, Le Nouen, Didier, additional, Métivier, Rémi, additional, Brosseau, Arnaud, additional, Héroguez, Valérie, additional, and Chemtob, Abraham, additional

Published
2019
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32. Micellisation électrostatique de copolymères à blocs double-hydrophiles

Author

PHIMPHACHANH, Anthony, MATHONNAT, Mélody, Pinaud, Julien, Lacroix-Desmazes, Patrick, Destarac, Mathias, Cottet, Hervé, Chamieh, Joseph, Leclercq, Laurent, Marcotte, Nathalie, IN, Martin, Gerardin, Corine, Laboratoire Charles Coulomb (L2C), Université de Montpellier (UM)-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), Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), 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), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), 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
[CHIM.POLY]Chemical Sciences/Polymers, [CHIM]Chemical Sciences, [PHYS.COND.CM-SCM]Physics [physics]/Condensed Matter [cond-mat]/Soft Condensed Matter [cond-mat.soft], ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2017

34. Electrostatic micellization of double-hydrophilic block copolymers

Author

PHIMPHACHANH, Anthony, MATHONNAT, Mélody, Pinaud, Julien, Lacroix-Desmazes, Patrick, Destarac, Mathias, Cottet, Herve, Marcotte, Nathalie, Gerardin, Corine, IN, Martin, Laboratoire Charles Coulomb (L2C), Université de Montpellier (UM)-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), Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), 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), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), 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
[CHIM.POLY]Chemical Sciences/Polymers, [PHYS.COND.CM-MS]Physics [physics]/Condensed Matter [cond-mat]/Materials Science [cond-mat.mtrl-sci], [CHIM]Chemical Sciences, [PHYS.COND.CM-SCM]Physics [physics]/Condensed Matter [cond-mat]/Soft Condensed Matter [cond-mat.soft], ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2017

35. Polymer-assisted extraction of palladium from supported catalysts in supercritical carbon dioxide

Author

Li, W.S. Jennifer, Pinot, Jordanna, Causse, Jérémy, Poirot, Hélène, Pinaud, Julien, Bouilhac, Cécile, Negrell, Claire, Simonaire, Herve, Barth, Danielle, Lacroix-Desmazes, Patrick, 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), Laboratoire Réactions et Génie des Procédés (LRGP), Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Séparative de Marcoule (ICSM - UMR 5257), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), BARTH, Danielle, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), 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), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-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
[SPI]Engineering Sciences [physics], [SPI] Engineering Sciences [physics], [SPI.GPROC] Engineering Sciences [physics]/Chemical and Process Engineering, [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2017

39. In Situ Generated Ruthenium–Arene Catalyst for Photoactivated Ring‐Opening Metathesis Polymerization through Photolatent N‐Heterocyclic Carbene Ligand

Author

Pinaud, Julien, primary, Trinh, Thi Kim Hoang, additional, Sauvanier, David, additional, Placet, Emeline, additional, Songsee, Sriprapai, additional, Lacroix‐Desmazes, Patrick, additional, Becht, Jean‐Michel, additional, Tarablsi, Bassam, additional, Lalevée, Jacques, additional, Pichavant, Loïc, additional, Héroguez, Valérie, additional, and Chemtob, Abraham, additional

Published
2017
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40. Recyclage des métaux nobles/stratégiques par des copolymères complexants en voie CO2 supercritique

Author

Lacroix-Desmazes, Patrick, Gasc, Fabien, Causse, Jérémy, Li, W.S. Jennifer, Pinot, Jordanna, Simonaire, Herve, Negrell, Claire, Pinaud, Julien, Bouilhac, Cécile, Barth, Danielle, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-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), Institut de Chimie Séparative de Marcoule (ICSM - UMR 5257), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Laboratoire Réactions et Génie des Procédés (LRGP), Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), 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), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-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), and BARTH, Danielle

Subjects
[SPI]Engineering Sciences [physics], [SPI] Engineering Sciences [physics], [SPI.GPROC] Engineering Sciences [physics]/Chemical and Process Engineering, [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering
Abstract

communication orale O22; National audience

Published
2016

42. In Situ Generated Ruthenium–Arene Catalyst for Photoactivated Ring‐Opening Metathesis Polymerization through Photolatent N‐Heterocyclic Carbene Ligand.

Author

Pinaud, Julien, Trinh, Thi Kim Hoang, Sauvanier, David, Placet, Emeline, Songsee, Sriprapai, Lacroix‐Desmazes, Patrick, Becht, Jean‐Michel, Tarablsi, Bassam, Lalevée, Jacques, Pichavant, Loïc, Héroguez, Valérie, and Chemtob, Abraham

Subjects
*RUTHENIUM, *AROMATIC compounds, *PHOTOACTIVATION, *POLYMERIZATION, *CARBENE derivatives
Abstract

Abstract: 1,3‐Bis(mesityl)imidazolium tetraphenylborate (IMesH+ BPh4−) can be synthesized in one step by anion metathesis between the corresponding imidazolium chloride and sodium tetraphenylborate. In the presence of 2‐isopropylthioxanthone (sensitizer), an IMes N‐heterocyclic carbene (NHC) ligand can be photogenerated under irradiation at 365 nm through coupled electron/proton transfer reactions. By combining this tandem NHC photogenerator system with metathesis inactive [RuCl2(p‐cymene)]2 precatalyst, the highly active RuCl2(p‐cymene)(IMes) complex can be formed in situ, enabling a complete ring‐opening metathesis polymerization (ROMP) of norbornene in the matter of minutes at room temperature. To the best of our knowledge, this is the first example of a photogenerated NHC. Its exploitation in photoROMP has resulted in a simplified process compared to current photocatalysts, because only stable commercial or easily synthesized reagents are required. [ABSTRACT FROM AUTHOR]

Published
2018
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43. Sequential Functionalization of Janus-Type Dendrimer-Like Poly(ethylene oxide)s with Camptothecin and Folic Acid

Author

FENG, Xiaoshuang, PINAUD, Julien, CHAIKOF, Elliot L., TATON, Daniel, GNANOU, Yves, Laboratoire de Chimie des Polymères Organiques (LCPO), Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC), Lab Biomol Mat Res (LBMR), Emory University [Atlanta, GA], Team 1 LCPO : Polymerization Catalyses & Engineering, and Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)

Subjects
dendrimer-like, folic acid, [CHIM.POLY]Chemical Sciences/Polymers, WOS:000291363200010, camptothecin, poly(ethylene oxide), bioconjugates, dendrimer, conjugation
Abstract

ISSN: 0887-624X; International audience; Janus-type dendrimer-like poly(ethylene oxide)s (PEOs) of 1st, 2nd, and 3rd generation carrying terminal hydroxyl functions on one side and cleavable ketal groups on the other were used as substrates to conjugate folic acid as a folate receptor and camptothecin (CPT) as a therapeutic drug in a sequential fashion. The conjugation of both FA and CPT was accomplished by "click chemistry" based on the 1,3 dipolar cycloaddition coupling reaction. First, the hydroxyl functions present at one face of Janus-type dendrimer-like PEOs were transformed into alkyne groups through a simple Williamson-type etherification reaction. Next, the ketals carried by the other face of the dendrimer-like PEOs were hydrolyzed, yielding twice as many hydroxyls which were subsequently subjected to an esterification reaction using 2-bromopropionic bromide. Before substituting azides for the bromide of 2-bromopropionate esters just generated in the presence of NaN(3), an azido-containing amidified FA derivative was reacted through click chemistry with alkyne functions introduced on the other face of the dendrimer-like PEOs. A purposely designed alkyne-functionalized biomolecule derived from CPT was conjugated to the azido functions carried by the dendritic PEOs by a second "click reaction"' In this case, twice as many CPT as FA moieties were finally conjugated to the two faces of the Janus-type dendrimer-like PEOs, the numbers of folate and CPT introduced being 2 and 4, 4 and 8, and 8 and 16 for samples of 1st, 2nd, and 3rd generation, respectively (route A). An alternate route for functionalizing the dendrimer-like PEO of 1st generation consisted, first, in conjugating the azido-containing CPT onto the alkyne groups present on one face of the dendritic PEO scaffold. The alkyne-functionalized FA was further introduced by click chemistry after the bromides of 2-bromopropionate esters were chemically transformed into azido groups. The corresponding prodrug thus contains 2 CPT and 4 FA external moieties (route B). Every reaction step product was thoroughly characterized by (1)H NMR spectroscopy. A preliminary investigation into the water solution properties of these functionalized dendritic PEOs is also presented.

Published
2011

44. Sequential functionalization of janus-type dendrimer-like poly(ethylene oxide)s with camptothecin and folic acid

Author

Gnanou, Yves, Taton, Daniel, Feng, Xiao-Shuang, Pinaud, Julien, Laboratoire de Chimie des polymères organiques (LCPO), and Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.POLY]Chemical Sciences/Polymers
Abstract

International audience; Janus-type dendrimer-like poly(ethylene oxide)s (PEOs) of 1st, 2nd, and 3rd generation carrying terminal hydroxyl functions on one side and cleavable ketal groups on the other were used as substrates to conjugate folic acid as a folate receptor and camptothecin (CPT) as a therapeutic drug in a sequential fashion. The conjugation of both FA and CPT was accomplished by "click chemistry" based on the 1,3 dipolar cycloaddition coupling reaction. First, the hydroxyl functions present at one face of Janus-type dendrimer-like PEOs were transformed into alkyne groups through a simple Williamson-type etherification reaction. Next, the ketals carried by the other face of the dendrimer-like PEOs were hydrolyzed, yielding twice as many hydroxyls which were subsequently subjected to an esterification reaction using 2-bromopropionic bromide. Before substituting azides for the bromide of 2-bromopropionate esters just generated in the presence of NaN3, an azido-containing amidified FA derivative was reacted through click chemistry with alkyne functions introduced on the other face of the dendrimer-like PEOs. A purposely designed alkyne-functionalized biomolecule derived from CPT was conjugated to the azido functions carried by the dendritic PEOs by a second "click reaction." In this case, twice as many CPT as FA moieties were finally conjugated to the two faces of the Janus-type dendrimer-like PEOs, the numbers of folate and CPT introduced being 2 and 4, 4 and 8, and 8 and 16 for samples of 1st, 2nd, and 3rd generation, respectively (route A). An alternate route for functionalizing the dendrimer-like PEO of 1st generation consisted, first, in conjugating the azido-containing CPT onto the alkyne groups present on one face of the dendritic PEO scaffold. The alkyne-functionalized FA was further introduced by click chemistry after the bromides of 2-bromopropionate esters were chemically transformed into azido groups. The corresponding prodrug thus contains 2 CPT and 4 FA external moieties (route B). Every reaction step product was thoroughly characterized by 1H NMR spectroscopy. A preliminary investigation into the water solution properties of these functionalized dendritic PEOs is also presented.

Published
2011

45. Step-growth Polymerization of Terephtaldehyde Catalyzed by N-Heterocyclic Carbenes

Author

PINAUD, Julien, KARI, Vijayakrishna, TATON, Daniel, GNANOU, Yves, Laboratoire de Chimie des Polymères Organiques (LCPO), Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC), Team 1 LCPO : Polymerization Catalyses & Engineering, Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC), and RICHARD, Dominique

Subjects
[CHIM.POLY] Chemical Sciences/Polymers, step-growth polymerization, [CHIM.POLY]Chemical Sciences/Polymers, Breslow intermediate, N-heterocyclic carbine, organocatalysis, benzoin condensation
Abstract

International audience; Benzoin condensation consists in reacting two aldehyde functions through a resonance-stabilized enaminol-type intermediate called the Breslow intermediate. This communication describes for the first time the use of N-heterocyclic carbenes (NHCs) as organic catalysts for the step-growth polymerization of a bis-aldehyde monomer, namely terephtaldehyde, which leads to poly(l,4-phenylene-l-oxo-2-hydroxyethylene) referred to as polybenzoin. These NHC-catalyzed polymerizations presumably involve the formation of Breslow intermediates. The effect of the NHCs catalyst activity and of the solvent polarity on the kinetics of the polymerization and on the formation of linear and cyclic polybenzoins is discussed.

Published
2009

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