OTTOU, Winnie Nzahou; BOURICHON, Damien; VIGNOLLE, Joan; WIROTIUS, Anne-Laure; ROBERT, Frédéric; LANDAIS, Yannick; SOTIROPOULOS, Jean-Marc; MIQUEU, Karinne; TATON, Daniel

doi:10.1002/chem.201500594

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OTTOU, Winnie Nzahou
Laboratoire de Chimie des Polymères Organiques [LCPO]

BOURICHON, Damien

VIGNOLLE, Joan

Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering

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Chemistry - A European Journal. 2015, vol. 21, n° 26, p. 9447-9453

Wiley-VCH Verlag

Résumé en anglais

Among 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.< Réduire

Mots clés en anglais

TO-TAIL DIMERIZATION

RING-OPENING POLYMERIZATION

reaction mechanisms

polymerization

organocatalysis

N-heterocyclic carbenes

density functional calculations

GENERATION

ORGANOCATALYSTS

UMPOLUNG

REACTIVITY

METHYL-METHACRYLATE

DOMINO REACTIONS

ACRYLATES

MECHANISM

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

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