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hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorKOELLER, Sylvain
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorKADOTA, Joji
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorPERUCH, Frédéric
IDREF: 152900748
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorDEFFIEUX, Alain
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorPINAUD, Noël
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorPIANET, Isabelle
hal.structure.identifierLaboratoire de Pharmacochimie
dc.contributor.authorMASSIP, Stéphane
hal.structure.identifierLaboratoire de Pharmacochimie
dc.contributor.authorLÉGER, Jean-Michel
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorDESVERGNE, Jean-Pierre
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorBIBAL, Brigitte
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2010
dc.identifier.issn0947-6539
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20589
dc.description.abstractEnThe mechanism of the ring-opening polymerization (ROP) of lactide catalyzed by two partner hydrogen-bonding organocatalysts was explored. New amidoindoles 4a,c, thioamidoindoles 4b,d, amidobenzimidazoles 5a,c, and thioamidobenzimidazoles 5b,c were synthesized and used as activators of the monomer. In the solid state and in solution, compounds 4 and 5 showed a propensity for self-association, which was evaluated. (Thio)Amides 4 and 5 do catalyze the ROP of lactide in the presence of a cocatalyst, tertiary amine 3a or 3b, which activates the growing polymer chain through hydrogen-bonding. Reactions were conducted in 2-24 h at 20 degrees C; conversion yields ranged between 22 and 100%. A detailed study of the intermolecular interactions undertaken between the participating species showed that, as expected, simultaneous weak hydrogen bonds do exist to activate the reagents. Moreover, interactions have been revealed between the partner catalysts 4/5+3. ROP catalyzed by these partner activators is thus governed by multiple dynamic equilibria. The latter should be judiciously adjusted to fine-tune the catalytic properties of (thio)amides and organocatalysts, more generally.
dc.language.isoen
dc.publisherWiley-VCH Verlag
dc.subject.enhydrogen bonds
dc.subject.enring-opening polymerization
dc.subject.enpartner catalysts
dc.subject.enorganocatalysis
dc.subject.enlactides
dc.title.en(Thio)Amidoindoles and (Thio)Amidobenzimidazoles: An Investigation of Their Hydrogen-Bonding and Organocatalytic Properties in the Ring-Opening Polymerization of Lactide
dc.typeArticle de revue
dc.identifier.doi10.1002/chem.200902912
dc.subject.halChimie/Polymères
bordeaux.journalChemistry - A European Journal
bordeaux.page4196-4205
bordeaux.volume16
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue14
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-00503141
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-00503141v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Chemistry%20-%20A%20European%20Journal&rft.date=2010&rft.volume=16&rft.issue=14&rft.spage=4196-4205&rft.epage=4196-4205&rft.eissn=0947-6539&rft.issn=0947-6539&rft.au=KOELLER,%20Sylvain&KADOTA,%20Joji&PERUCH,%20Fr%C3%A9d%C3%A9ric&DEFFIEUX,%20Alain&PINAUD,%20No%C3%ABl&rft.genre=article


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