Synthesis and characterization of fluoro-substituted polyphenylthiophenes for charge storage applications

A series of fluoro-substituted phenylthiophene monomers has been synthesized with high isolated yields (71–90%). Generalized coupling reactions have been developed for the series with a Pd(dppf)Cl2 catalyst and via Zn-complex mediated reactions. The controlled electropolymerization of monomers yielded polymeric materials which, when cycled, exhibited reversible redox reactions in both the n- and p-doped states with high cycling efficiencies. The doping levels and polymerization potentials were strongly correlated with the electronic character of the monomers based on the Hammett model. This methodology suggests a theoretical scheme for the development of other high charge-capacity polymeric materials.