Computational evaluation of the sulfonyl radical as a universal leaving group for RAFT polymerisation

Ganna Gryn'ova, Tamaz Guliashvili, Krzysztof Matyjaszewski, Michelle L. Coote

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The present study investigates the performance of the sulfonyl radical, i.e. •SO2Ph, as a universal leaving group in reversible addition-fragmentation chain-transfer (RAFT) polymerisation. The sulfonyl radical is widely used as a radical initiator and has already been proved successful as a leaving group in an atom-transfer radical polymerisation. Our results, obtained using high-level ab initio computational methodology under relevant experimental conditions, indicate superior performance of the sulfonyl compared with a reference cyanoisopropyl group in controlling RAFT of a wide range of monomers. Importantly, the presence of sulfonyl chain ends in the polymers so formed opens attractive possibilities for further functionalisation. Potential synthetic routes to the R-sulfonyl RAFT agents are discussed.

Original languageEnglish
Pages (from-to)308-313
Number of pages6
JournalAustralian Journal of Chemistry
Volume66
Issue number3
DOIs
Publication statusPublished - 2013
Externally publishedYes

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