SYNTHESIS AND CHARACTERIZATION OF FLUORO-SUBSTITUTED POLYPHENYLTHIOPHENES FOR CHARGE STORAGE APPLICATIONS

A series of fluoro-substituted phenylthiophene monomers has been synth esized with high isolated yields (71-90%). Generalized coupling reacti ons have been developed for the series with a Pd(dppf)Cl-2 catalyst an d via Zn-complex mediated reactions. The controlled electropolymerizat ion of monomers yielded polymeric materials which, when cycled, exhibi ted reversible redox reactions in both the n- and p-doped states with high cycling efficiencies. The doping levels and polymerization potent ials were strongly correlated with the electronic character of the mon omers based on the Hammett model. This methodology suggests a theoreti cal scheme for the development of other high charge-capacity polymeric materials.