Derivatization of fullerenes by electrosynthesis

In this paper the electrochemical derivatization of fullerenes in the case of C-60 is described. The property of fullerenes to form di- or tri- anions by electrochemical reduction at less cathodic potentials is used for chemical derivatization. These anions react with alkyl or aryl halides, e.g. iodomethane, iodobenzene, 1-iodonaphthalene and 1,2-diiodobenzene in benzonitrile solution. Depending on the electrochemical conditions and the chemical structure, di- or tetra-alkyl and aryl fullerenes, respectively, are formed. The electrosynthesis is followed by cyclic voltammetry. The reaction products are isolated by high performance liquid chromatography (HPLC) and characterized by H-1 NMR spectroscopy and mass spectrometry.