Synthesis of hydroazafullerene C59HN, the parent hydroheterofullerene

• Published in: Nature (London) 1996-09, Vol.383 (6596), p.147-150
• Main Authors: Keshavarz-K, Majid, González, Rosario, Hicks, Robin G., Srdanov, Gordana, Srdanov, Vojislav I., Collins, Tasha G., Hummelen, Jan Cornelis, Bellavia-Lund, Cheryl, Pavlovich, James, Wudl, Fred, Holczer, Karoly
• Format: Article
• Language: English
• Subjects: Chemistry; Elements and non-metal compounds (oxides, hydroxides, hydrides, sulfides, carbides, ...); Exact sciences and technology; Fullerenes; Humanities and Social Sciences; Inorganic chemistry and origins of life; letter; multidisciplinary; Organic chemistry; Preparations and properties; Science; Science (multidisciplinary)
• ISSN: 0028-0836; 1476-4687
• DOI: 10.1038/383147a0

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 C 59 N, 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, C 59 HN. The electronic, vibrational and 13 C NMR spectroscopic features of C 59 HN are similar to those of the dimer 2 , except for the signature of the sp 3 (C–H) carbon. C 59 HN should open the door to a new chemistry of heterofullerenes.