ENANTIOSELECTIVE ELECTROPOLYMERIZATION OF ANILINE IN THE PRESENCE OF (-CAMPHORSULFONATE OR (-)-CAMPHORSULFONATE ION - A FACILE ROUTE TO CONDUCTING POLYMERS WITH PREFERRED ONE-SCREW-SENSE HELICITY())

The first and remarkably facile synthesis of optically active polyanil ine has been achieved via the enantioselective electropolymerization o f aniline on indium-tin-oxide-coated glass electrodes in aqueous solut ion containing (1S)-(+)- or (1R)-(-)-10-camphorsulfonic acid (HCSA). T he dark green films of conducting polyemeraldine salt formed under ele ctrostatic conditions (+ 1.1 V versus Ag/AgCl) exhibited strong circul ar dichroism (c.d.) spectra typical of polymers possessing helical chi rality. The quantitative reversal of the c.d. spectrum of the salt gro wn in (+)-HCSA as opposed to (-)-HCSA suggests that electropolymerizat ion 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 pol yanilines should facilitate studies of their use in asymmetric synthes is and in chiral chromatography.