SYNTHESIS OF HYDROAZAFULLERENE C59HN, THE PARENT HYDROHETEROFULLERENE

THE electronic and geometric properties of C-60 can be perturbed by re placing one or more carbon atoms of the fullerene skeleton with an ato m of a different element. Exchange of one carbon atom with nitrogen, a trivalent atom with a lone pair of electrons, produces the azafullere ne radical C59N; which is isoelectronic with the C-60 radical anion. T he process is slightly similar to doping silicon with phosphorus(1). W e have previously described the synthesis of the azafullerene dimer(2) ; here we report the bulk preparation of the simplest azafullerene, C5 9HN. The electronic, vibrational and C-13 NMR spectroscopic features o f C59HN are similar to those of the dimer(2), except for the signature of the sp(3) (C-H) carbon. C59HN should open the door to a new chemis try of heterofullerenes.