389873-34-1Relevant articles and documents
Synthesis of a polymerizable fluorosurfactant for the construction of stable nanostructured proton-conducting membranes
Wadekar, Mohan N.,Jager, Wolter F.,Sudhoelter, Ernst J. R.,Picken, Stephen J.
experimental part, p. 6814 - 6819 (2010/11/24)
The synthesis of the polymerizable fluorinated surfactant sodium 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-(4-vinylphenyl)ethoxy) ethanesulfonate (1) and a number of related fluorocarbon compounds is described. Compound 1 is synthesized using a copper-mediated cross-coupling reaction of 4-bromobenzaldehyde and sodium 5-iodooctafluoro-3-oxapentanesulfonate. The resulting benzaldehyde is converted to a styrene unit using a Wittig reaction with methyltriphenylphosphonium bromide in acetonitrile, using DBU as a base. This strategy for converting an iodo-functionalized fluorosurfactant to a styrene-containing fluorosurfactant is highly efficient because both reactions are performed in polar solvents and are compatible with the sulfonate moiety. In addition, the copper-mediated cross-coupling reaction is most efficient with electron-poor aryl bromides like 4-bromobenzaldehyde. We wish to employ 1 for the construction of nanostructured membranes by polymerization of 1 in a microemulsion or in lyotropic liquid crystalline phases.
