The SuFEx (sulfonyl fluoride exchange reaction) mediated synthesis of BPA-polysulfate from bisphenol A-bis(fluorosulfate) ('AA') and bis(silylether) ('BB') monomers is a step-growth polymerization method capable of tolerating stoichiometric imbalance. In addition to the primary reaction of AA + BB, fluorosulfates were observed to undergo homocoupling thereby leading to additional reactivity of AA + AA. High molecular weight polysulfate can thus be obtained in three ways; A) 1:1 equivalents AA:BB, B) excess AA relative to BB, or C) solely from the AA monomer. Methods B) and C) thereby ensure the resulting polysulfate polymer is end-capped with reactive fluorosulfate groups. The ability to manipulate these functional handles is demonstrated through the attachment of a UV-traceable, OTBS-substituted nile red dye using post-polymerization SuFEx reactivity.

Synthesis of BPA-polysulfate: Tolerance toward stoichiometric imbalance leads to end-cap-functionalizable fluorosulfate groups

248th National Meeting (2014)

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