Synthesis of hydroazafullerene C59HN, the parent hydroheterofuIlerene

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.

On-Ball Doping of Fullerenes: The Electronic Structure of C59N Dimers from Experiment and Theory

We present the first studies of the electronic structure of the heterofullerene (C59N)2 using electron energy-loss spectroscopy in transmission, photoemission spectroscopy, and density functional theory calculations. Both the C 1s excitation spectra and valence band photoemission show negligible occupation of the C-derived lowest unoccupied electronic states and indicate localization of the excess electrons at the N atoms. The experimental results, together with the detailed analysis of our theoretical data, provide compelling evidence for the chemical picture of a triply coordinated N atom with a lone pair in each heterofullerene unit, and confirm the theoretically predicted “6,6 closed” structure for the dimer

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