Electropolymerization of anilines linked with triarylamines as a redox-active function

Electropolymerization of aniline derivatives linked with a triarylamine moiety (TAA) as a redox-active function was investigated in various supporting electrolyte-solvent-electrode systems. A firmly adhering and conductive polyaniline film carrying TAA could be formed on a glassy carbon electrode by a cyclic potential sweep electrolysis of 4-{4-[N,N,-bis(4-bromophenyl)amino]phenyl}propyl (2-aminophenyl)acetate in dichloromethane containing n-Bu₄NClO₄ in the range from -0.5 to 1.80 V vs Ag/AgCl. The polymer-coated carbon electrode thus formed exhibits stable and broad redox peaks in the cyclic voltammograms even after 20 cycles. Similar cyclic potential sweep electrolysis of the related TAA-functionalized aniline derivatives was also carried out but redox-active conductive films were not formed. The effects of solvent, supporting electrolyte, electrode material are discussed.