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From the N-Heterocyclic Carbene-Catalyzed Conjugate Addition of Alcohols to the Controlled Polymerization of (Meth)acrylates

dc.rights.licenseopen
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorOTTOU, Winnie Nzahou
dc.contributor.authorBOURICHON, Damien
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorVIGNOLLE, Joan
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorWIROTIUS, Anne-Laure
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorROBERT, Frédéric
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorLANDAIS, Yannick
dc.contributor.authorSOTIROPOULOS, Jean-Marc
dc.contributor.authorMIQUEU, Karinne
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.issued2015
dc.identifier.issn0947-6539
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20238
dc.description.abstractEnAmong various N-heterocyclic carbenes (NHCs) tested, only 1,3-bis(tert-butyl)imidazol-2-ylidene (NHCtBu) proved to selectively promote the catalytic conjugate addition of alcohols onto (meth)acrylate substrates. This rather rare example of NHC-catalyzed 1,4-addition of alcohols was investigated as a simple means to trigger the polymerization of both methyl methacrylate and methyl acrylate (MMA and MA, respectively). Well-defined -alkoxy poly(methyl (meth)acrylate) (PM(M)A) chains, the molar masses of which could be controlled by the initial [(meth)acrylate](0)/[ROH](0) molar ratio, were ultimately obtained in N,N-dimethylformamide at 25 degrees C. A hydroxyl-terminated poly(ethylene oxide) (PEO-OH) macro-initiator was also employed to directly access PEO-b-PMMA amphiphilic block copolymers. Investigations into the reaction mechanism by DFT calculations revealed the occurrence of two competitive concerted pathways, involving either the activation of the alcohol or that of the monomer by NHCtBu.
dc.language.isoen
dc.publisherWiley-VCH Verlag
dc.subject.enTO-TAIL DIMERIZATION
dc.subject.enRING-OPENING POLYMERIZATION
dc.subject.enreaction mechanisms
dc.subject.enpolymerization
dc.subject.enorganocatalysis
dc.subject.enN-heterocyclic carbenes
dc.subject.endensity functional calculations
dc.subject.enGENERATION
dc.subject.enORGANOCATALYSTS
dc.subject.enUMPOLUNG
dc.subject.enREACTIVITY
dc.subject.enMETHYL-METHACRYLATE
dc.subject.enDOMINO REACTIONS
dc.subject.enACRYLATES
dc.subject.enMECHANISM
dc.title.enFrom the N-Heterocyclic Carbene-Catalyzed Conjugate Addition of Alcohols to the Controlled Polymerization of (Meth)acrylates
dc.typeArticle de revue
dc.identifier.doi10.1002/chem.201500594
dc.subject.halChimie/Polymères
bordeaux.journalChemistry - A European Journal
bordeaux.page9447-9453
bordeaux.volume21
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue26
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-01366544
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-01366544v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Chemistry%20-%20A%20European%20Journal&rft.date=2015&rft.volume=21&rft.issue=26&rft.spage=9447-9453&rft.epage=9447-9453&rft.eissn=0947-6539&rft.issn=0947-6539&rft.au=OTTOU,%20Winnie%20Nzahou&BOURICHON,%20Damien&VIGNOLLE,%20Joan&WIROTIUS,%20Anne-Laure&ROBERT,%20Fr%C3%A9d%C3%A9ric&rft.genre=article


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