Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 30, Pages 12596-12603Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja3030643
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Funding
- Ignite Energy Resources Ltd
- Licella Pty Ltd
- Australian Research Council [LP100200339, FT0990485]
- Gritton Scholarship
- Studienstiftung des deutschen Volkes
- Australian Research Council [FT0990485, LP100200339] Funding Source: Australian Research Council
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A new methodology has been developed for preparing alpha-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 alpha-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; D = 1.16-1.38). We also show that this carbonyl-azide CTA can be used as a universal platform for the synthesis of alpha-end-functionalized polymers in a one-pot RAFT polymerization/isocyanate click procedure.
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