In the presence of manganese(III) acetate dihydrate [Mn(OAc)₃•2H₂O], the reaction of [60]fullerene with tetraethyl methylenediphosphonate, diethyl cyanomethylphosphonate or diethylphosphonoacetic acid ethyl ester in refluxing chlorobenzene afforded the corresponding methano[60]fullerene organophosphonates C₆₀C(R)PO(OEt)₂ [1, R＝PO(OEt)₂; 2, R＝COOEt; 3, R＝CN], respectively. This reaction produced fewer by-products and needed less reaction time. Therefore it is superior to the Bingel reaction for the preparation of compounds 1, 2 and 3. In addition, compared with C₆₀, compounds 1 and 2 had negative shifts but 3 had a posive shift of 40 mV in reduction half-wave potentials (E_1/2) determined by cyclic voltammetry. These data indicate that the introduction of electro-attracting groups such as cyano-group to fullerene ball might improve the electrochemical properties and synthesize fullerene derivatives with strong electron-accepting ability.

Key words: synthesis, electrochemical property, cyclic voltammetry, mono-methano[60]fullerene organophosphonate