Derivatization of fullerenes by electrosynthesis

In this paper the electrochemical derivatization of fullerenes in the case of C60 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 1H NMR spectroscopy and mass spectrometry.