Computational Evaluation of the Sulfonyl Radical as a Universal Leaving Group for RAFT Polymerisation

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.

SEEK ID: https://publications.h-its.org/publications/517

DOI: 10.1071/CH12452

Research Groups: Computational Carbon Chemistry

Publication type: Journal

Journal: Australian Journal of Chemistry

Citation: Aust. J. Chem. 66(3):308

Date Published: 2013

Registered Mode: by DOI

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

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Citation
Gryn'ova, G., Guliashvili, T., Matyjaszewski, K., & Coote, M. L. (2013). Computational Evaluation of the Sulfonyl Radical as a Universal Leaving Group for RAFT Polymerisation. In Australian Journal of Chemistry (Vol. 66, Issue 3, p. 308). CSIRO Publishing. https://doi.org/10.1071/ch12452
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Created: 5th Nov 2019 at 14:34

Last updated: 5th Mar 2024 at 21:23

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