Para-Fluoro Postpolymerization Chemistry of Poly(pentafluorobenzyl

Sep 7, 2017 - Department of Chemistry, University of Surrey - Guildford, Surrey GU2 7XH, United Kingdom. ∥ Department of Chemistry, University Colle...
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Article pubs.acs.org/Macromolecules

Para-Fluoro Postpolymerization Chemistry of Poly(pentafluorobenzyl methacrylate): Modification with Amines, Thiols, and Carbonylthiolates Janina-Miriam Noy,† Ann-Katrin Friedrich,† Kyle Batten,‡ Mathamsanqa N. Bhebhe,‡ Nicolas Busatto,§ Rhiannon R. Batchelor,† Ariella Kristanti,† Yiwen Pei,†,‡,∥ and Peter J. Roth*,†,‡,§ †

Centre for Advanced Macromolecular Design (CAMD), University of New South Wales, Kensington, Sydney, NSW 2052, Australia Nanochemistry Research Institute (NRI) and Department of Chemistry, Curtin University, Bentley, Perth, WA 6102, Australia § Department of Chemistry, University of Surrey - Guildford, Surrey GU2 7XH, United Kingdom ∥ Department of Chemistry, University College London, London WC1E 6BT, United Kingdom ‡

S Supporting Information *

ABSTRACT: A methacrylic polymer undergoing highly efficient para-fluoro substitution reactions is presented. A series of well-defined poly(2,3,4,5,6-pentafluorobenzyl methacrylate) (pPFBMA) homopolymers with degrees of polymerization from 28 to 132 and Đ ≤ 1.29 was prepared by the RAFT process. pPFBMA samples were atactic (with triad tacticity apparent in 1H and 19F NMR spectra) and soluble in most organic solvents. pPFBMA reacted quantitatively through para-fluoro substitution with a range of thiols (typically 1.1 equiv of thiol, base, RT,