SuFEx‐Based Polysulfonate Formation from Ethenesulfonyl Fluoride–Amine Adducts

Wang, Hua; Zhou, Feng; Ren, Gerui; Zheng, Qinheng; Chen, Hongli; Gao, Bing; Klivansky, Liana; Liu, Yi; Wu, Bin; Xu, Qingfeng; Lu, Jianmei; Sharpless, K. Barry; Wu, Peng

doi:10.1002/ange.201701160

Title: SuFEx‐Based Polysulfonate Formation from Ethenesulfonyl Fluoride–Amine Adducts

Journal Article · Thu May 18 00:00:00 EDT 2017 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.201701160· OSTI ID:1374471

Wang, Hua ^[1]; Zhou, Feng ^[2]; Ren, Gerui ^[3]; Zheng, Qinheng ^[4]; Chen, Hongli ^[4]; Gao, Bing ^[4]; Klivansky, Liana ^[5]; Liu, Yi ^[5]; Wu, Bin ^[6]; Xu, Qingfeng ^[6]; Lu, Jianmei ^[6]; Sharpless, K. Barry ^[4]; Wu, Peng ^[7]

Department of Chemical Physiology The Scripps Research Institute 10550 North Torrey Pines Road La Jolla CA 92037 USA, Department of Chemistry The Scripps Research Institute 10550 North Torrey Pines Road La Jolla CA 92037 USA
Department of Chemistry The Scripps Research Institute 10550 North Torrey Pines Road La Jolla CA 92037 USA, College of Chemistry, Chemical Engineering and Materials Science Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University Suzhou 215123 P.R. China
Department of Chemistry The Scripps Research Institute 10550 North Torrey Pines Road La Jolla CA 92037 USA, Department of Applied Chemistry School of Food Science and Biotechnology Zhejiang Gongshang University Hangzhou 310018 P.R. China
Department of Chemistry The Scripps Research Institute 10550 North Torrey Pines Road La Jolla CA 92037 USA
The Molecular Foundry Lawrence Berkeley National Laboratory Berkeley CA 94720 USA
College of Chemistry, Chemical Engineering and Materials Science Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University Suzhou 215123 P.R. China
Department of Chemical Physiology The Scripps Research Institute 10550 North Torrey Pines Road La Jolla CA 92037 USA

Abstract The SuFEx‐based polycondensation between bisalkylsulfonyl fluorides (AA monomers) and bisphenol bis( t ‐butyldimethylsilyl) ethers (BB monomers) using [Ph ₃ P=N−PPh ₃ ] ⁺ [HF ₂ ] ⁻ as the catalyst is described. The AA monomers were prepared via the highly reliable Michael addition of ethenesulfonyl fluoride and amines/anilines while the BB monomers were obtained from silylation of bisphenols by t ‐butyldimethylsilyl chloride. With these reactions, a remarkable diversity of monomeric building blocks was achieved by exploiting readily available amines, anilines, and bisphenols as starting materials. The SuFEx‐based polysulfonate formation reaction exhibited excellent efficiency and functional group tolerance, producing polysulfonates with a variety of side chain functionalities in >99 % conversion within 10 min to 1 h. When bearing an orthogonal group on the side chain, the polysulfonates can be further functionalized via click‐chemistry‐based post‐polymerization modification.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1374471

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Vol. 129 Journal Issue: 37; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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