SYNTHESIS AND PROPERTIES OF POLY(3-HYDROQUINONYLPYRROLE)

Poly(3-hydroquinonylpyrrole) was synthesized by electrochemical polymerization and characterized by cyclic voltammetry and spectroelectrochemistry. The polymer was made by direct electropolymerization of the monomer and by demethylation of poly(3-(2,5-dimethoxyphenyl)pyrrole). The positive shift of over 60 mV in the oxidation potential of hydroquinone in poly(3-hydroquinonylpyrrole) compared to related substituted hydroquinones is evidence of electronic interaction between the substituent and the polypyrrole backbone. The spectroelectrochemistry revealed an absorption at 360 nm at the potential at which the hydroquinone was oxidized to quinone. For films with comparable charge storage, poly(3-quinonylpyrrole) absorbs only 15% as much light in the visible portion of the spectrum as oxidized polypyrrole. A convenient synthesis is given for a pyrrole monomer with a protected hydroquinone in the 3-position.