The electronic and geometric properties of C60 can be perturbed by replacing one or more carbon atoms of the fullerene skeleton with an atom of a different element. Exchange of one carbon atom with nitrogen, a trivalent atom with a lone pair of electrons, produces the azafullerene radical C59N·, which is isoelectronic with the C60 radical anion. The process is slightly similar to doping silicon with phosphorus. We have previously described the synthesis of the azafullerene dimer; here we report the bulk preparation of the simplest azafullerene, C59HN. The electronic, vibrational and 13C NMR spectroscopic features of C59HN are similar to those of the dimer, except for the signature of the sp3 (C-H) carbon. C59HN should open the door to a new chemistry of heterofullerenes.
