Afficher la notice abrégée

Polyaldol Synthesis by Direct Organocatalyzed Crossed Polymerization of Bis(ketones) and Bis(aldehydes)

dc.rights.licenseopen
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorLIU, Na
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorMARTIN, Anthony
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorROBERT, Frédéric
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorVINCENT, Jean-Marc
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorLANDAIS, Yannick
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]
hal.structure.identifierTeam 2 LCPO : Biopolymers & Bio-sourced Polymers
dc.contributor.authorCRAMAIL, Henri
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.issued2014
dc.identifier.issn0024-9297
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20243
dc.description.abstractEnSynthesis of polyaldols consisting of beta-keto alcohol monomer units is described. These polymers were obtained by direct step-growth polymerization of purposely designed bifunctional enolizable bis(ketone) monomers playing the role of nucleophilic donors, and activated nonenolizable bis(aldehyde)s serving as electrophilic acceptors. Monofunctional ketone and aldehyde homologues were first synthesized as models to establish the aldol reaction conditions using reaction partners at stoichiometry. A bifunctional organocatalytic system consisting of pyrrolidine in conjunction with acetic acid allowed performing polyaldolizations of stoichiometric amounts of the bis(aldehyde) and the bis(ketone) in solution in THF, DMSO, or DMF, at room temperature. However, polar solvents and/or prolonged reaction time induced further aldol reactions between aldol units of polymer chains, as indicated by the relatively broad molecular weight distribution of related polyaldols observed by size exclusion chromatography. Analysis by NMR spectroscopy confirmed the formation of beta-keto alcohol units, but also evidenced that the latter were also partly dehydrated into conjugated ketones via a crotonization reaction (from 20 to 33% depending on the structure of the initial monomers).
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.subject.enTISHCHENKO REACTION
dc.subject.enKETONIC RESINS
dc.subject.enSELF-POLYMERIZATION
dc.subject.enISOTETRONIC ACIDS
dc.subject.enASYMMETRIC ALLYLATION POLYMERIZATION
dc.subject.enCHIRAL (ACYLOXY)BORANE CATALYST
dc.subject.enBAYLIS-HILLMAN POLYMERIZATION
dc.subject.enCHAIN FUNCTIONAL POLYESTERS
dc.subject.enMUKAIYAMA ALDOL REACTION
dc.subject.enTRANSITION-METAL ALKYLS
dc.title.enPolyaldol Synthesis by Direct Organocatalyzed Crossed Polymerization of Bis(ketones) and Bis(aldehydes)
dc.typeArticle de revue
dc.identifier.doi10.1021/ma402108y
dc.subject.halChimie/Polymères
bordeaux.journalMacromolecules
bordeaux.page525-533
bordeaux.volume47
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue2
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-01366330
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-01366330v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Macromolecules&rft.date=2014&rft.volume=47&rft.issue=2&rft.spage=525-533&rft.epage=525-533&rft.eissn=0024-9297&rft.issn=0024-9297&rft.au=LIU,%20Na&MARTIN,%20Anthony&ROBERT,%20Fr%C3%A9d%C3%A9ric&VINCENT,%20Jean-Marc&LANDAIS,%20Yannick&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