Heterofullerene
Heterofullerenes are classes of fullerenes, at least one carbon atom is replaced by another element.{{Cite journal | last1 = Vostrowsky | first1 = O. | last2 = Hirsch | first2 = A. | doi = 10.1021/cr050561e | title = Heterofullerenes | journal = Chemical Reviews | volume = 106 | issue = 12 | pages = 5191–5207 | year = 2006 | pmid = 17165685}}{{cite journal | last1 = Hummelen | first1 = Jan C. | last2 = Bellavia-Lund | first2 = Cheryl | last3 = Wudl | first3 = Fred | year = 1999 | title = Heterofullerenes. Fullerenes and Related Structures | journal = Topics in Current Chemistry | volume = 199 | pages = 93–134 | doi = 10.1007/3-540-68117-5_3}} Based on spectroscopy, substitutions have been reported with boron (borafullerenes),{{Cite journal |author1=Chai, Y. |author2=Guo, T. |author3=Jin, C. |author4=Haufler, R. E. |author5=Chibante, L. P. F. |author6=Fure, J. |author7=Wang, L. |author8=Alford, J. M. |author9=Smalley, R. E. | doi = 10.1021/j100173a002 | title = Fullerenes with metals inside | journal = The Journal of Physical Chemistry | volume = 95 | issue = 20 | pages = 7564 | year = 1991}}{{Cite journal | last1 = Muhr | first1 = H. -J. | last2 = Nesper | first2 = R. | last3 = Schnyder | first3 = B. | last4 = Kötz | first4 = R. | title = The boron heterofullerenes C59B and C69B: Generation, extraction, mass spectrometric and XPS characterization | doi = 10.1016/0009-2614(95)01451-9 | journal = Chemical Physics Letters | volume = 249 | issue = 5–6 | pages = 399 | year = 1996 | bibcode=1996CPL...249..399M}} nitrogen (azafullerenes),{{Cite journal | last1 = Averdung | first1 = J. | last2 = Luftmann | first2 = H. | last3 = Schlachter | first3 = I. | last4 = Mattay | first4 = J. | title = Aza-dihydro[60]fullerene in the gas phase. A mass-spectrometric and quantumchemical study | doi = 10.1016/0040-4020(95)00361-B | journal = Tetrahedron | volume = 51 | issue = 25 | pages = 6977 | year = 1995 | doi-access = free}}{{Cite journal | last1 = Lamparth | first1 = I. | last2 = Nuber | first2 = B. | last3 = Schick | first3 = G. | last4 = Skiebe | first4 = A. | last5 = Grösser | first5 = T. | last6 = Hirsch | first6 = A. | doi = 10.1002/anie.199522571 | title = C59N+ and C69N+: Isoelectronic Heteroanalogues of C60 and C70 | journal = Angewandte Chemie International Edition in English | volume = 34 | issue = 20 | pages = 2257 | year = 1995}} oxygen (oxafullerenes),{{Cite journal | last1 = Christian | first1 = J. F. | last2 = Wan | first2 = Z. | last3 = Anderson | first3 = S. L. | doi = 10.1016/0009-2614(92)80134-W | title = O++C60•C60O+ production and decomposition, charge transfer, and formation of C59O+. Dopeyball or [CO@C58]+ | journal = Chemical Physics Letters | volume = 199 | issue = 3–4 | pages = 373 | year = 1992 |bibcode = 1992CPL...199..373C}} arsenic (arsafullerenes), germanium (germafullerenes),{{Cite journal | last1 = Ohtsuki | first1 = T. | last2 = Ohno | first2 = K. | last3 = Shiga | first3 = K. | last4 = Kawazoe | first4 = Y. | last5 = Maruyama | first5 = Y. | last6 = Masumoto | first6 = K. | doi = 10.1103/PhysRevB.60.1531 | title = Formation of As- and Ge-doped heterofullerenes | journal = Physical Review B | volume = 60 | issue = 3 | pages = 1531 | year = 1999 |bibcode = 1999PhRvB..60.1531O}} phosphorus (phosphafullerenes),{{cite journal|doi=10.1002/(SICI)1521-3749(199902)625:2<175::AID-ZAAC175>3.0.CO;2-2|author1=Möschel, C. |author2=Jansen, M. |year=1999|title= Darstellung stabiler Phosphor-Heterofullerene im Hochfrequenzofen|journal= Z. Anorg. Allg. Chem.|volume= 625|pages= 175–177|issue=2}} silicon (silafullerenes),{{Cite journal| doi = 10.1063/1.478598 | title = Photolysis experiments on SiC mixed clusters: From silicon carbide clusters to silicon-doped fullerenes | journal = The Journal of Chemical Physics | volume = 110 | issue = 14 | pages = 6927–6938 | year = 1999 |bibcode = 1999JChPh.110.6927P | last1 = Pellarin | first1 = M. | last2 = Ray | first2 = C. | last3 = Lermé | first3 = J. | last4 = Vialle | first4 = J. L. | last5 = Broyer | first5 = M. | last6 = Blase | first6 = X. | last7 = Kéghélian | first7 = P. | last8 = Mélinon | first8 = P. | last9 = Perez | first9 = A.}} iron (ferrafullerenes), copper (cuprafullerenes), nickel (nickelafullerenes), rhodium (rhodafullerenes){{Cite journal | last1 = Branz | first1 = W. | last2 = Billas | first2 = I. M. L. | last3 = Malinowski | first3 = N. | last4 = Tast | first4 = F. | last5 = Heinebrodt | first5 = M. | last6 = Martin | first6 = T. P. | doi = 10.1063/1.477410 | title = Cage substitution in metal–fullerene clusters | journal = The Journal of Chemical Physics | volume = 109 | issue = 9 | pages = 3425 | year = 1998 |bibcode = 1998JChPh.109.3425B}} and iridium (iridafullerenes).{{Cite journal| doi = 10.1016/S0965-9773(99)00301-3 | title = Experimental and computational studies of heterofullerenes | journal = Nanostructured Materials | volume = 12 | issue = 5–8 | pages = 1071–1076 | year = 1999 | last1 = Billas | first1 = I.M.L. | last2 = Branz | first2 = W. | last3 = Malinowski | first3 = N. | last4 = Tast | first4 = F. | last5 = Heinebrodt | first5 = M. | last6 = Martin | first6 = T.P. | last7 = Massobrio | first7 = C. | last8 = Boero | first8 = M. | last9 = Parrinello | first9 = M.}}
Reports on isolated heterofullerenes are limited to those based on nitrogen Harris, D.J. (1993) "Discovery of Nitroballs: Research in Fullerene Chemistry" http://www.usc.edu/CSSF/History/1993/CatWin_S05.html {{Webarchive|url=https://web.archive.org/web/20151129202804/http://www.usc.edu/CSSF/History/1993/CatWin_S05.html |date=2015-11-29}}{{Cite journal | last1 = Hummelen | first1 = J. C. | last2 = Knight | first2 = B. | last3 = Pavlovich | first3 = J. | last4 = Gonzalez | first4 = R. | last5 = Wudl | first5 = F. | title = Isolation of the Heterofullerene C59N as Its Dimer (C59N)2 | doi = 10.1126/science.269.5230.1554 | journal = Science | volume = 269 | issue = 5230 | pages = 1554–1556 | year = 1995 | pmid = 17789446|bibcode = 1995Sci...269.1554H | url = https://pure.rug.nl/ws/files/3620734/1995HummelenScience.pdf | hdl = 11370/ffe5ba8c-5336-4aed-9c78-0a26f31d459d | s2cid = 31270587 | hdl-access = free}}{{Cite journal | last1 = Keshavarz-K | first1 = M. | last2 = González | first2 = R. | last3 = Hicks | first3 = R. G. | last4 = Srdanov | first4 = G. | last5 = Srdanov | first5 = V. I. | last6 = Collins | first6 = T. G. | last7 = Hummelen | first7 = J. C. | last8 = Bellavia-Lund | first8 = C. | last9 = Pavlovich | first9 = J. | last10 = Wudl | doi = 10.1038/383147a0 | first10 = F. | last11 = Holczer | first11 = K. | title = Synthesis of hydroazafullerene C59HN, the parent hydroheterofullerene | journal = Nature | volume = 383 | issue = 6596 | pages = 147 | year = 1996 |bibcode = 1996Natur.383..147K | s2cid = 4315682}}{{Cite journal | last1 = Nuber | first1 = B. | last2 = Hirsch | first2 = A. | doi = 10.1039/CC9960001421 | title = A new route to nitrogen heterofullerenes and the first synthesis of (C69N)2 | journal = Chemical Communications | issue = 12 | pages = 1421 | year = 1996}}{{Cite journal | last1 = Zhang | first1 = G. | last2 = Huang | first2 = S. | last3 = Xiao | first3 = Z. | last4 = Chen | first4 = Q. | last5 = Gan | first5 = L. | last6 = Wang | first6 = Z. | doi = 10.1021/ja805072h | title = Preparation of Azafullerene Derivatives from Fullerene-Mixed Peroxides and Single Crystal X-ray Structures of Azafulleroid and Azafullerene | journal = Journal of the American Chemical Society | volume = 130 | issue = 38 | pages = 12614–12615 | year = 2008 | pmid = 18759401}} and oxygen.{{Cite journal | last1 = Xin | first1 = N. | last2 = Huang | first2 = H. | last3 = Zhang | first3 = J. | last4 = Dai | first4 = Z. | last5 = Gan | first5 = L. | title = Fullerene Doping: Preparation of Azafullerene C59NH and Oxafulleroids C59O3 and C60O4 | doi = 10.1002/anie.201202777 | journal = Angewandte Chemie International Edition | volume = 51 | issue = 25 | pages = 6163–6166 | year = 2012 | pmid = 22573566}}