Regioselective chemical modification of fullerene by destructive electrophilic reaction in polyphosphoric acid/phosphorus pentoxide

Abstract

An adduct of electrophilic reaction between C 60 and 4-(2,4,6-trimethylphenoxy)benzamide was afforded in a polyphosphoric acid (PPA)/phosphorus pentoxide (P 2O 5) medium at 130 °C. The matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrum of the adduct showed that multiple destructive acylation reactions of 4-(2,4,6-trimethylphenoxy)benzamide on C 60 had occurred to give hexakis(4-(2,4,6-trimethylphenoxy)benzoyl)-substituted C 54. On the basis of the combined results of optical studies, it could be presumably concluded that the regioselective destruction and addition pathway on the C 60 framework might have predominantly occurred to six-membered rings.