Electrochemical Synthesis of PEDOT Derivatives Bearing Imidazolium-Ionic Liquid Moieties

Novel poly(3,4-ethylenedioxythiophene) (PEDOT) polymers bearing imidazolium-ionic liquid moieties were synthesized by electrochemical polymerizations. For this purpose, new functional monomers were synthesized having an 3,4-ethylenedioxythiophene (EDOT) unit and an imidazolium-ionic liquid with different anions such as tetrafluoroborate (BF4-), bis(trifluoromethane)sulfonimide ((CF3SO2)(2)N-), and hexafluorophosphate (PF6-). Next, polymer films were obtained by electrochemical synthesis in dicholoromethane solutions. Obtained polymers were characterized, revealing the characteristics of PEDOT in terms of electrochemical and spectroelectrochemical properties, FTIR, H-1 NMR, and AFM microscopy. Interestingly, the hydrophobic character of electropolymerized films could be modified depending on the anion type. The hydrophobicity followed the trend PF6- > (CF3SO2)(2)N- > BF4- > pure PEDOT as determined by water contact angle measurements. Furthermore, the polymers could be dissolved in a range of polar organic solvents such as dimethylformamide, propylene carbonate, and dimethyl sulfoxide making these polymers interesting candidates for wet processing methods. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3010-3021, 2009