One-pot RAFT/"click" chemistry via isocyanates: efficient synthesis of α-end-functionalized polymers

Guillaume Gody, Christian Rossner, John Moraes, Philipp Vana, Thomas Maschmeyer, Sébastien Perrier

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83 Citations (Scopus)

Abstract

A new methodology has been developed for preparing α-functional polymers in a one-pot simultaneous polymerization/isocyanate "click" reaction. Our original synthetic strategy is based on the preparation of a carbonyl-azide chain transfer agent (CTA) precursor that undergoes the Curtius rearrangement in situ during reversible addition-fragmentation chain transfer (RAFT) polymerization yielding well-controlled α-isocyanate modified polymers. This strategy overcomes numerous difficulties associated with the synthesis of a polymerization mediator bearing an isocyanate at the R group and with the handling of such a reactive functionality. This new carbonyl-azide CTA can control the polymerization of a wide range of monomers, including (meth)acrylates, acrylamides, and styrenes (M n = 2-30 kDa; = 1.16-1.38). We also show that this carbonyl-azide CTA can be used as a universal platform for the synthesis of α-end-functionalized polymers in a one-pot RAFT polymerization/isocyanate "click" procedure.

Original languageEnglish
Pages (from-to)12596-12603
Number of pages8
JournalJournal of the American Chemical Society
Volume134
Issue number30
DOIs
Publication statusPublished - 1 Aug 2012
Externally publishedYes

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