The first and remarkably facile synthesis of optically active polyaniline has been achieved via the enantioselective electropolymerization of aniline on indium-tin-oxide-coated glass electrodes in aqueous solution containing (IS)-(+)- or (1R)-(-)-10-camphorsulfonic acid (HCSA). The dark green films of conducting polyemeraldine salt formed under electrostatic conditions (+ L1 V versus Ag/AgC1) exhibited strong circular dichroism (c.d.) spectra typical of polymers possessing helical chirality. The quantitative reversal of the c.d. spectrum of the salt grown in (+)-HCSA as opposed to (-)-HCSA suggests that electropolymerization is highly enantioselective, with one helical screw of the polymer chain being preferentially produced depending on the hand of the CSA- anion incorporated. The ready electrosynthesis of optically active polyanilines should facilitate studies of their use in asymmetric synthesis and in chiral chromatography.
Посилання на статтю:
Enantioselective electropolymerization of aniline in the presence of (+)- or (-)-camphorsulfonate ion: a facile route to conducting polymers with preferred one-screw-sense helicity / Mir Reza Majidi, Leon A. P. Kane-Maguire* and Gordon G. Wallace // Polymer. – 1994. – Vol 35. – P. 3113-3115.