Two-fold addition reaction of silylene to C 60 : structural and electronic properties of a bis-adduct.

The addition reaction of C 60 with silylene 1 , a silicon analog of carbene, yielded the corresponding bis-adduct 3 . The structure of 3 was determined by single-crystal X-ray structure analysis, representing the first example of a crystal structure of a silirane (silacyclopropane) derivative of fullerenes. Electrochemical measurements confirmed that the redox potentials of 3 are shifted cathodically compared to those of the parent mono-adduct 2 . Density functional theory (DFT) calculations provided the basis for the electronic properties of compound 3 .