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 (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.
Wadekar
Mohan N
MN
Laboratory of NanoStructured Materials, Department of Chemical Engineering DelftChemTech, Delft University of Technology, Julianalaan 136,2628BL Delft, The Netherlands.
Jager
Wolter F
WF
Sudhölter
Ernst J R
EJ
Picken
Stephen J
SJ
D000476:Alkanesulfonates / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D008567:Membranes, Artificial; D015394:Molecular Structure; D049329:Nanostructures / Q000737:chemistry*; D011522:Protons; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry
D000476:Alkanesulfonates; D005456:Fluorescent Dyes; D008567:Membranes, Artificial; D011522:Protons; D013501:Surface-Active Agents; C555277:sodium 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-(4-vinylphenyl)ethoxy)ethanesulfonate