Electrochemical properties of soluble fullerene derivatives

The Family of fullerene derivatives obtained by 1,3-dipolar cycloaddition of azomethine ylides to C-60 is colloquially termed fulleropyrrolidines. In this payer, we report the synthesis and the electrochemical properties of a series of fulleropyrrolidine derivatives. All compounds are characterized by the presence of a solubilizing mTEG group. In addition, a derivative containing a thiophene moiety, covalently attached to the pyrrolidine ring has been studied. Cyclic voltammetry measurements, performed also at low temperatures, allowed the observation of five fullerene-centered reductions for all the species. Adsorption phenomena, however, were found associated to the last reduction processes in the thiophene-fulleropyrrolidine conjugate. Moreover, thanks to the increased solubility of the latter species in polar solvents (acetonitrile-dichloromethane mixtures) its anodic polymerization was carried out, leading to a conducting film still retaining the redox properties of the fullerene derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.