Synthesis of a Polymerizable Fluorosurfactant for the Construction of Stable Nanostructured Proton-Conducting Membranes

The synthesis of the polymerizable fluorinated surfactant sodium 1,1,2 2-tetrafluoro-2-(1,1 2 2-tetrafluoro-2-(4-vinylphenyl)ethoxy)ethanesulfonate (I) and a number or dated fluorocarbon compounds is described Compound I is synthesized using a copper-mediated cross-coupling reaction of 4-bromobenzaldehyde and sodium 5-iodoctafluoro-3-oxapentanesulfonate The resulting benzalde-hyde is converted to a sty, cue unit using a Wittig reaction with methyltriphenylphosphonium bromide in accetonitrile. using DBU as a base This strategy for convening an iodo-functionalized fluorosurfactant to a styrene-containing fluorosurfactant is highly efficient because both reactions ale performed m polar solvents and ale compatible with the sulfonate moiety In addition the copper-mediated cross-coupling reaction is most efficient with electron-poor aryl biomides like 4-bromolienzaldehyde We wish to employ I for the construction of nanostructured memberanes by polymerization 0f I in a microemulsion or in lyotiopic liquid crystalline phases