Photophysical, Photochemical, and Chemical Reactions of Fullerenes and Dihydrofullerene Derivatives

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Abstract

The fullerenes C60 and C70 give high yields of their triplet states on irradiation with visible or near-UV light. The triplets transfer energy to oxygen, producing singlet molecular oxygen with near unit efficiency. Electron transfer to triplet C60 occurs readily from electron donors to produce the radical anion. C60 is readily oxidized by excited high-potential photosensitizers to the radical cation, and also reacts with dimethyl dioxirane to give a mixture of the epoxide and a novel dioxolane adduct, a dihydrofullerene ketal. Some novel dihydrofullerenes can be prepared. In two cases at least, they also give high yields of the triplet state and, subsequently, singlet oxygen on irradiation with visible or near UV light. Photoreaction of C60 triplet with electron-rich compounds appears to be an efficient route to monofunctionalized derivatives. A very reactive enamine can be prepared by photochemical [2+2] addition of an ynamine; self-sensitized photooxidation (which makes the enamine difficult to isolate) cleaves it to a ketoamide, in over 50% yield from C60.