Dithiolation of [60]fullerene with aliphatic primary thiols initiated by n-butylamine via aerobic oxidation reaction

A facile aerobic oxidation reaction of [60]fullerene with aliphatic primary thiols initiated by n-butylamine was studied. Interestingly, the reaction yielded liquid mixtures upon solvent evaporation, contrary to the typical formation of solid mixtures. The reaction products were purified using HPLC to isolate the fullerene dithiol epoxide compound (2), which was extensively characterized by ¹H NMR, ¹³C NMR, HRMS, and UV–Vis spectra. Plausible reaction mechanisms leading to the formation of the observed products were proposed. Computational simulations and control experiment were conducted to elucidate the proposed reaction mechanisms. The electrochemical behavior of 1,2-O-4,15-(n-C₅H₁₁S)₂C₆₀ (2) was investigated, revealing its instability upon gradual reduction.