PHOTOCHEMICAL AND THERMAL-REACTIONS OF C-60 WITH N-SUCCINIMIDYL 4-AZIDO-2,3,5,6-TETRAFLUOROBENZOATE - A NEW METHOD FOR FUNCTIONALIZATION OF C-60

The first example of a photochemical reaction between C-60 and an N-hydroxysuccinimide (NHS) functionalized perfluorophenyl azide (PFPA) is reported. Photolysis of a chlorobenzene solution of C-60 and N-succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate (1) at 300 nm gave exclusively the monoadduct azamethanofullerene 2 in 10% yield (39% based on recovered C-60) The reaction is believed to take place via the addition of the photogenerated, highly reactive nitrene intermediate to a 6,6 double bond of C-60. The NHS active ester group present in 2 served as a site for attachment of other molecules by way of an acylation reaction. For example, 2 was allowed to react with L-glutamic acid diethyl ester or benzylamine to give the corresponding amides 3 or 4. Thermal reaction of C-60 and 1 in chlorobenzene at 105-108 degrees C gave the same adduct 2 in 25% yield (45% based on recovered C-60).