5 years ago

SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride-Amine Adducts

SuFEx-Based Polysulfonate Formation from Ethenesulfonyl Fluoride-Amine Adducts
Qinheng Zheng, Bing Gao, Peng Wu, Feng Zhou, Bin Wu, Jianmei Lu, Liana Klivansky, Yi Liu, Qingfeng Xu, Hua Wang, Hongli Chen, K. Barry Sharpless, Gerui Ren
The SuFEx-based polycondensation between bisalkylsulfonyl fluorides (AA monomers) and bisphenol bis(t-butyldimethylsilyl) ethers (BB monomers) using [Ph3P=N−PPh3]+[HF2]− 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. The sulfur(VI) fluoride exchange (SuFEx)-based polycondensation reaction between bisalkylsulfonyl fluorides and bisphenol bis(t-butyldimethylsilyl) ethers using [Ph3P=N−PPh3]+[HF2]− as the catalyst was developed. Polysulfonates synthesized via this method can be further functionalized using click chemistry based transformations orthogonal to SuFEx.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701160

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