The pattern of additions to fullerenes

Abstract

Conjugation in C 60 is not as extensive as was originally anticipated because, for various reasons, the pentagon rings avoid containing double bonds. As a consequence, there is extensive bond localization and the molecule, which is quite reactive, and displays superalkene rather than superaromatic properties. C 70 behaves in a similar fashion; other fullerenes may follow suit. Additions predominate and C 60 is particularly susceptible to nucleophilic attack. Added groups may also be readily replaced by nucleophiles, although the reaction mechanism is uncertain at present: The functionalized molecule tends to revert to the parent fullerene at moderate temperatures, and characterization of reaction products by mass spectrometry is thus particularly difficult. This fact, coupled with the complexity of the addition products, makes work with fullerenes exacting. A selection of reactions studied to date and the progress made towards identifying various patterns of addition are described.