Heterofullerenes are classes of fullerenes, at least one carbon atom is replaced by another element.[1][2] Based on spectroscopy, substitutions have been reported with boron (borafullerenes),[3][4] nitrogen (azafullerenes),[5][6] oxygen,[7] arsenic, germanium,[8] phosphorus,[9] silicon,[10][11] iron, copper, nickel, rhodium[11][12] and iridium.[11]
Reports on isolated heterofullerenes are limited to those based on nitrogen [13][14][15][16][17] and oxygen.[18]
Hummelen, Jan C.; Bellavia-Lund, Cheryl; Wudl, Fred (1999). "Heterofullerenes. Fullerenes and Related Structures". Topics in Current Chemistry. 199: 93–134. doi:10.1007/3-540-68117-5_3. Chai, Y.; Guo, T.; Jin, C.; Haufler, R. E.; Chibante, L. P. F.; Fure, J.; Wang, L.; Alford, J. M.; Smalley, R. E. (1991). "Fullerenes with metals inside". The Journal of Physical Chemistry. 95 (20): 7564. doi:10.1021/j100173a002. Lamparth, I.; Nuber, B.; Schick, G.; Skiebe, A.; Grösser, T.; Hirsch, A. (1995). "C59N+ and C69N+: Isoelectronic Heteroanalogues of C60 and C70". Angewandte Chemie International Edition in English. 34 (20): 2257. doi:10.1002/anie.199522571. Pellarin, M.; Ray, C.; Lermé, J.; Vialle, J. L.; Broyer, M.; Blase, X.; Kéghélian, P.; Mélinon, P.; Perez, A. (1999). "Photolysis experiments on SiC mixed clusters: From silicon carbide clusters to silicon-doped fullerenes". The Journal of Chemical Physics. 110 (14): 6927–6938. Bibcode:1999JChPh.110.6927P. doi:10.1063/1.478598. Billas, I.M.L.; Branz, W.; Malinowski, N.; Tast, F.; Heinebrodt, M.; Martin, T.P.; Massobrio, C.; Boero, M.; Parrinello, M. (1999). "Experimental and computational studies of heterofullerenes". Nanostructured Materials. 12 (5–8): 1071–1076. doi:10.1016/S0965-9773(99)00301-3. Branz, W.; Billas, I. M. L.; Malinowski, N.; Tast, F.; Heinebrodt, M.; Martin, T. P. (1998). "Cage substitution in metal–fullerene clusters". The Journal of Chemical Physics. 109 (9): 3425. Bibcode:1998JChPh.109.3425B. doi:10.1063/1.477410. Keshavarz-K, M.; González, R.; Hicks, R. G.; Srdanov, G.; Srdanov, V. I.; Collins, T. G.; Hummelen, J. C.; Bellavia-Lund, C.; Pavlovich, J.; Wudl, F.; Holczer, K. (1996). "Synthesis of hydroazafullerene C59HN, the parent hydroheterofullerene". Nature. 383 (6596): 147. Bibcode:1996Natur.383..147K. doi:10.1038/383147a0. S2CID 4315682. Nuber, B.; Hirsch, A. (1996). "A new route to nitrogen heterofullerenes and the first synthesis of (C69N)2". Chemical Communications (12): 1421. doi:10.1039/CC9960001421. Zhang, G.; Huang, S.; Xiao, Z.; Chen, Q.; Gan, L.; Wang, Z. (2008). "Preparation of Azafullerene Derivatives from Fullerene-Mixed Peroxides and Single Crystal X-ray Structures of Azafulleroid and Azafullerene". Journal of the American Chemical Society. 130 (38): 12614–12615. doi:10.1021/ja805072h. PMID 18759401. Xin, N.; Huang, H.; Zhang, J.; Dai, Z.; Gan, L. (2012). "Fullerene Doping: Preparation of Azafullerene C59NH and Oxafulleroids C59O3 and C60O4". Angewandte Chemie International Edition. 51 (25): 6163–6166. doi:10.1002/anie.201202777. PMID 22573566.
