Synthesis of hydroazafullerene C59HN, the parent hydroheterofullerene

THE electronic and geometric properties of C-60 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 C-60 radical anion. The process is slightly similar to doping silicon with phosphorus(1). We have previously described the synthesis of the azafullerene dimer(2); here we report the bulk preparation of the simplest azafullerene, C59HN. The electronic, vibrational and C-13 NMR spectroscopic features of 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 chemistry of heterofullerenes.