Preparation and photophysical studies of a fluorous phase-soluble fullerene derivative

We report the first synthesis of a well-characterized Teflon ponytail fullerene adduct (3) via the Hirsch-Bingel reaction with a malonate bearing two pefluorinated alkyl chains, This C tris-adduct shows excellent solubility in perfluorinated solvents, such as FC-72 and FC-75. Compound 3 was found to be an efficient sensitizer for singlet oxygen formation in fluorous media, which has potential in biphasic systems and in photobiology.