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Ring-Opening Polymerization of L-Lactide Efficiently Triggered by an Amido-Indole. X-ray Structure of a Complex between L-Lactide and the Hydrogen-Bonding Organocatalyst

dc.rights.licenseopen
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.authorDEFFIEUX, Alain
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 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.issued2009
dc.identifier.issn0002-7863
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20586
dc.description.abstractEnN-(3,5-Bis(trifluoromethyl)phenyl)-1H-indole-2-carboxamide le is an efficient hydrogen-bonding organocatalyst for the ring-opening polymerization Of L-lactide. This new catalytic species does control the dispersity (1.08) and molecular weight (3460 g/mol vs 3064 in theory) of the poly(L-lactides) prepared in 2 h. H-1 NMR analysis showed that compound le complexes L-lactide in CDCl3 through the two available NH groups (amide and indole). In particular, the catalytic species appeared to be mainly the H-bonding donor amide (le in extended conformation, alone or dimer (1e)(2)) and, to a Lesser extend, the dual H-bonding amido-indole (1e in its the pinched conformation). The first X-ray structure of the complex between a H-bonding organocatalyst and L-lactide also revealed a tight H-bonded network between the dimer (1e)(2) and L-lactide.
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.subject.enLIVING POLYMERIZATION
dc.subject.enDONORS
dc.subject.enDERIVATIVES
dc.subject.enCATALYSTS
dc.subject.enRECOGNITION
dc.title.enRing-Opening Polymerization of L-Lactide Efficiently Triggered by an Amido-Indole. X-ray Structure of a Complex between L-Lactide and the Hydrogen-Bonding Organocatalyst
dc.typeArticle de revue
dc.identifier.doi10.1021/ja906119t
dc.subject.halChimie/Polymères
bordeaux.journalJournal of the American Chemical Society
bordeaux.page15088-15130
bordeaux.volume131
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue42
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-00503817
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-00503817v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.date=2009&rft.volume=131&rft.issue=42&rft.spage=15088-15130&rft.epage=15088-15130&rft.eissn=0002-7863&rft.issn=0002-7863&rft.au=KOELLER,%20Sylvain&KADOTA,%20Joji&DEFFIEUX,%20Alain&PERUCH,%20Fr%C3%A9d%C3%A9ric&MASSIP,%20St%C3%A9phane&rft.genre=article


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