SYNTHESIS, CHARACTERIZATION AND ELECTROPOLYMERIZATION OF FERROCENE MONOMERS WITH ANILINE AND PHENOL SUBSTITUENTS

The synthesis and electrochemical properties of the ferrocene compounds (C5H5)Fe(C5H4 CH2NHRn), where R(n)=C6H5 (1), C6H4-3-NH2 (2), C6H4-3-OH (3) and (CH2)2NHC6H5 (4), are described. All compounds polymerize upon electrochemical oxidation of the phenyl portion of the complex in a CH3CN solution containing Bu4NClO4 as supporting electrolyte. The phenol-substituted complex shows unique polymerization behavior: adding NEt3 to the electrolysis solution greatly enhances the rate of film deposition. Electrochemical characterization of the films shows well-defined couples for the terrocene but no indication that the polymer backbones are electroactive. Spectroelectrochemical measurements show changes in the visible region of the spectrum characteristic for formation of the ferricinium cation, lambda(max) = 620 nm, upon oxidation. In the case of the polymer from 2 a moderately intense absorption at 480 nm is also recorded, which suggests that the polymer backbone may be electrochemically active.