One-Pot RAFT/鈥淐lick鈥?Chemistry via Isocyanates: Efficient Synthesis of 伪-End-Functionalized Polymers

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• 作者：Guillaume Gody ; Christian Rossner ; John Moraes ; Philipp Vana ; Thomas Maschmeyer ; S茅bastien Perrier
• 刊名：The Journal of the American Chemical Society
• 出版年：2012
• 出版时间：August 1, 2012
• 年：2012
• 卷：134
• 期：30
• 页码：12596-12603
• 全文大小：378K
• 年卷期：v.134,no.30(August 1, 2012)
• ISSN：1520-5126

文摘

A new methodology has been developed for preparing 伪-functional polymers in a one-pot simultaneous polymerization/isocyanate 鈥渃lick鈥?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鈥揻ragmentation chain transfer (RAFT) polymerization yielding well-controlled 伪-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鈥?0 kDa; 膼 = 1.16鈥?.38). We also show that this carbonyl-azide CTA can be used as a universal platform for the synthesis of 伪-end-functionalized polymers in a one-pot RAFT polymerization/isocyanate 鈥渃lick鈥?procedure.