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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
Publication Date
Sep 01, 2017
eScholarship - University of California
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The SuFEx-based polycondensation between bisalkylsulfonyl fluorides (AA monomers) and bisphenol bis(t-butyldimethylsilyl) ethers (BB monomers) using [Ph3 P=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.

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