Nucleophilic addition of functionalized alcohols to perfluorinated olefins has been an intensely studied transformation in organofluorine chemistry. This strategy affords commercially important fluoroelastomers having low surface energy, exceptional thermal– chemical resistance, and behave as good electrical insulation. Despite these advances, many fluoropolymers such as Teflon~(TM) are highly crystalline and, as a consequence, are difficult to process. We have successfully demonstrated a new, facile step-growth polymerization of commercially available bisphenols (1) and bis(trifluorovinyloxy) biphenyls (2) affording fluorinated aromatic vinylene ether (FAVE) polymers for thermosets and proton exchange membranes (PEMs) for fuel cells (Scheme 1). The fluorinated aryl ether polymers possess primarily internal fluoroolefins (CF=CF) from the expulsion of fluorine during the polymerization process. The FAVE polymers exhibit high thermal stability and are solution processable producing optically transparent, flexible films. The fluroolefin is chemically inert to various radical initiators, oxidations, and Lewis acids.
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