Afficher la notice abrégée

Facile Synthesis of Reversibly Crosslinked Poly(ionic liquid)-type Gels: Recyclable Supports for Organocatalysis by N-Heterocyclic Carbenes

dc.rights.licenseopen
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierDepartment of Chemistry [University of Warwick]
hal.structure.identifierSchool of Chemistry University of Birmingham
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorGARMENDIA, Sofiem
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorLAMBERT, Romain
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorWIROTIUS, Anne-Laure
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorVIGNOLLE, Joan
hal.structure.identifierSchool of Chemistry University of Birmingham
dc.contributor.authorDOVE, Andrew P.
hal.structure.identifierSchool of Chemistry University of Birmingham
dc.contributor.authorO’REILLY, Rachel K.
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorTATON, Daniel
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2018
dc.identifier.issn0014-3057
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20023
dc.description.abstractEnOwing to their broad modularity, polymeric versions of ionic liquids, referred to as poly(ionic liquids) (PILs), have attracted increasing attention as recyclable polymer-supported (pre)catalysts for various chemical transformations. Herein, an imidazolium-based statistical copolymer based on PIL (=coPIL) is specifically designed by free-radical copolymerization of styrene and 4-vinylbenzylethyl(benz)imidazolium chloride. A selective ion-exchange reaction can be subsequently achieved to incorporate bio-sourced difunctional sebacate-type counter-anions, causing the physical crosslinking of the coPIL precursor via electrostatic interactions between pendant imidazolium moieties and sebacate dianions. The as-obtained gel-type precursor exhibits a thermally latent behavior in THF, proving advantageous for a facile manipulation and practical use for organocatalysis. Upon heating, typically at 80 °C, interaction between the sebacate dianion and the proton in C2-position of the imidazolium moieties generates polymer-supported N-heterocyclic carbene units that act as catalytic active species towards NHC-organocatalyzed reactions, namely, benzoin condensation, transesterification and cyanosilylation. The PIL-based gel precursors can be restored, recycled and reused by simply cooling down, i.e. with no need of an external chemical reagent, due to the shift of the intramolecular equilibrium towards the formation of imidazolium sebacate-type units. Overall, this novel gel-type copolymeric platform shows a thermo-responsive behaviour, and proves particularly versatile for heterogeneous organocatalysis.
dc.language.isoen
dc.publisherElsevier
dc.subject.enN-Heterocyclic carbene
dc.subject.enOrganocatalysis
dc.subject.enPoly(ionic liquid)
dc.subject.enMasked-carbene
dc.title.enFacile Synthesis of Reversibly Crosslinked Poly(ionic liquid)-type Gels: Recyclable Supports for Organocatalysis by N-Heterocyclic Carbenes
dc.typeArticle de revue
dc.identifier.doi10.1016/j.eurpolymj.2018.07.031
dc.subject.halChimie/Polymères
dc.description.sponsorshipEuropeEuropean Joint Doctorate in Organocatalysis and Sustainable Polymers
bordeaux.journalEuropean Polymer Journal
bordeaux.page82-88
bordeaux.volume107
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-01863790
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-01863790v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=European%20Polymer%20Journal&rft.date=2018&rft.volume=107&rft.spage=82-88&rft.epage=82-88&rft.eissn=0014-3057&rft.issn=0014-3057&rft.au=GARMENDIA,%20Sofiem&LAMBERT,%20Romain&WIROTIUS,%20Anne-Laure&VIGNOLLE,%20Joan&DOVE,%20Andrew%20P.&rft.genre=article


Fichier(s) constituant ce document

FichiersTailleFormatVue

Il n'y a pas de fichiers associés à ce document.

Ce document figure dans la(les) collection(s) suivante(s)

Afficher la notice abrégée