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2020年1月25日 (土) 15:44時点における最新版

ヘテロフラーレン (heterofullerene) は、炭素原子が非炭素原子で置換されたフラーレンである。少なくとも1つの炭素原子が別の元素で置き換えられている^[1]^[2]。分光法に基づいて、ホウ素（ボラフラーレン）^[3]^[4]、窒素（アザフラーレン）^[5]^[6]、酸素^[7]、ヒ素、ゲルマニウム^[8]、リン^[9]、ケイ素^[10]、鉄、銅、ニッケル、ロジウム^[11]およびイリジウム^[12]置換が報告されている。分離されたヘテロフラーレンに関する報告は、窒素^[13]^[14]^[15]^[16]^[17]および酸素に基づくものに限定されている^[18]。

出典[編集]

[脚注の使い方]

^ Vostrowsky, O.; Hirsch, A. (2006). “Heterofullerenes”. Chemical Reviews 106 (12): 5191–5207. doi:10.1021/cr050561e. PMID 17165685.
^ 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. et al. (1991). “Fullerenes with metals inside”. The Journal of Physical Chemistry 95 (20): 7564. doi:10.1021/j100173a002.
^ Muhr, H. -J.; Nesper, R.; Schnyder, B.; Kötz, R. (1996). “The boron heterofullerenes C₅₉B and C₆₉B: Generation, extraction, mass spectrometric and XPS characterization”. Chemical Physics Letters 249 (5–6): 399. Bibcode: 1996CPL...249..399M. doi:10.1016/0009-2614(95)01451-9.
^ Averdung, J.; Luftmann, H.; Schlachter, I.; Mattay, J. (1995). “Aza-dihydro[60]fullerene in the gas phase. A mass-spectrometric and quantumchemical study”. Tetrahedron 51 (25): 6977. doi:10.1016/0040-4020(95)00361-B.
^ 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.
^ Christian, J. F.; Wan, Z.; Anderson, S. L. (1992). “O⁺+C_60•C₆₀O⁺ production and decomposition, charge transfer, and formation of C₅₉O⁺. Dopeyball or [CO@C₅₈]⁺”. Chemical Physics Letters 199 (3–4): 373. Bibcode: 1992CPL...199..373C. doi:10.1016/0009-2614(92)80134-W.
^ Ohtsuki, T.; Ohno, K.; Shiga, K.; Kawazoe, Y.; Maruyama, Y.; Masumoto, K. (1999). “Formation of As- and Ge-doped heterofullerenes”. Physical Review B 60 (3): 1531. Bibcode: 1999PhRvB..60.1531O. doi:10.1103/PhysRevB.60.1531.
^ Möschel, C.; Jansen, M. (1999). “Darstellung stabiler Phosphor-Heterofullerene im Hochfrequenzofen”. Z. Anorg. Allg. Chem. 625 (2): 175–177. doi:10.1002/(SICI)1521-3749(199902)625:2<175::AID-ZAAC175>3.0.CO;2-2.
^ “Photolysis experiments on SiC mixed clusters: From silicon carbide clusters to silicon-doped fullerenes”. The Journal of Chemical Physics 110 (14): 6927–6938. (1999). Bibcode: 1999JChPh.110.6927P. doi:10.1063/1.478598.
^ 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.
^ “Experimental and computational studies of heterofullerenes”. Nanostructured Materials 12 (5–8): 1071–1076. (1999). doi:10.1016/S0965-9773(99)00301-3.
^ Harris, D.J. (1993). Discovery of Nitroballs: Research in Fullerene Chemistry.
^ Hummelen, J. C.; Knight, B.; Pavlovich, J.; Gonzalez, R.; Wudl, F. (1995). “Isolation of the Heterofullerene C₅₉N as Its Dimer (C₅₉N)₂”. Science 269 (5230): 1554–1556. Bibcode: 1995Sci...269.1554H. doi:10.1126/science.269.5230.1554. PMID 17789446.
^ Keshavarz-K, M.; González, R.; Hicks, R. G.; Srdanov, G.; Srdanov, V. I.; Collins, T. G.; Hummelen, J. C.; Bellavia-Lund, C. et al. (1996). “Synthesis of hydroazafullerene C₅₉HN, the parent hydroheterofullerene”. Nature 383 (6596): 147. Bibcode: 1996Natur.383..147K. doi:10.1038/383147a0.
^ 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.

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[1] Vostrowsky, O.; Hirsch, A. (2006). “Heterofullerenes”. Chemical Reviews 106 (12): 5191–5207. doi:10.1021/cr050561e. PMID 17165685.

[2] 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.

[3] Chai, Y.; Guo, T.; Jin, C.; Haufler, R. E.; Chibante, L. P. F.; Fure, J.; Wang, L.; Alford, J. M. et al. (1991). “Fullerenes with metals inside”. The Journal of Physical Chemistry 95 (20): 7564. doi:10.1021/j100173a002.

[4] Muhr, H. -J.; Nesper, R.; Schnyder, B.; Kötz, R. (1996). “The boron heterofullerenes C₅₉B and C₆₉B: Generation, extraction, mass spectrometric and XPS characterization”. Chemical Physics Letters 249 (5–6): 399. Bibcode: 1996CPL...249..399M. doi:10.1016/0009-2614(95)01451-9.

[5] Averdung, J.; Luftmann, H.; Schlachter, I.; Mattay, J. (1995). “Aza-dihydro[60]fullerene in the gas phase. A mass-spectrometric and quantumchemical study”. Tetrahedron 51 (25): 6977. doi:10.1016/0040-4020(95)00361-B.

[6] 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.

[7] Christian, J. F.; Wan, Z.; Anderson, S. L. (1992). “O⁺+C_60•C₆₀O⁺ production and decomposition, charge transfer, and formation of C₅₉O⁺. Dopeyball or [CO@C₅₈]⁺”. Chemical Physics Letters 199 (3–4): 373. Bibcode: 1992CPL...199..373C. doi:10.1016/0009-2614(92)80134-W.

[8] Ohtsuki, T.; Ohno, K.; Shiga, K.; Kawazoe, Y.; Maruyama, Y.; Masumoto, K. (1999). “Formation of As- and Ge-doped heterofullerenes”. Physical Review B 60 (3): 1531. Bibcode: 1999PhRvB..60.1531O. doi:10.1103/PhysRevB.60.1531.

[9] Möschel, C.; Jansen, M. (1999). “Darstellung stabiler Phosphor-Heterofullerene im Hochfrequenzofen”. Z. Anorg. Allg. Chem. 625 (2): 175–177. doi:10.1002/(SICI)1521-3749(199902)625:2<175::AID-ZAAC175>3.0.CO;2-2.

[10] “Photolysis experiments on SiC mixed clusters: From silicon carbide clusters to silicon-doped fullerenes”. The Journal of Chemical Physics 110 (14): 6927–6938. (1999). Bibcode: 1999JChPh.110.6927P. doi:10.1063/1.478598.

[11] 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.

[Billas-12] “Experimental and computational studies of heterofullerenes”. Nanostructured Materials 12 (5–8): 1071–1076. (1999). doi:10.1016/S0965-9773(99)00301-3.

[13] Harris, D.J. (1993). Discovery of Nitroballs: Research in Fullerene Chemistry.

[14] Hummelen, J. C.; Knight, B.; Pavlovich, J.; Gonzalez, R.; Wudl, F. (1995). “Isolation of the Heterofullerene C₅₉N as Its Dimer (C₅₉N)₂”. Science 269 (5230): 1554–1556. Bibcode: 1995Sci...269.1554H. doi:10.1126/science.269.5230.1554. PMID 17789446.

[15] Keshavarz-K, M.; González, R.; Hicks, R. G.; Srdanov, G.; Srdanov, V. I.; Collins, T. G.; Hummelen, J. C.; Bellavia-Lund, C. et al. (1996). “Synthesis of hydroazafullerene C₅₉HN, the parent hydroheterofullerene”. Nature 383 (6596): 147. Bibcode: 1996Natur.383..147K. doi:10.1038/383147a0.

[16] 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.

[17] 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.

[18] 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.

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 {{出典の明記|date=2016年1月10日 (日) 03:30 (UTC)}}
-'''ヘテロフラーレン''' (heterofullerene) は、[[炭素]]原子が非炭素原子で置換された[[フラーレン]]である。少なくとも1つの炭素原子が別の元素で置き換えられている<ref>{{Cite journal|last=Vostrowsky|first=O.|last2=Hirsch|first2=A.|year=2006|title=Heterofullerenes|journal=Chemical Reviews|volume=106|issue=12|pages=5191–5207|DOI=10.1021/cr050561e|PMID=17165685|PMC=}}</ref><ref>{{Cite journal|last=Hummelen|first=Jan C.|last2=Bellavia-Lund|first2=Cheryl|last3=Wudl|first3=Fred|year=1999|title=Heterofullerenes. Fullerenes and Related Structures|url=|journal=Topics in Current Chemistry|volume=199|issue=|pages=93–134|DOI=10.1007/3-540-68117-5_3}}</ref>。[[分光法]]に基づいて、[[ホウ素]]（'''[[ボラフラーレン]]'''）<ref>{{Cite journal|last=Chai, Y.|last2=Guo, T.|last3=Jin, C.|last4=Haufler, R. E.|last5=Chibante, L. P. F.|last6=Fure, J.|last7=Wang, L.|last8=Alford, J. M.|last9=Smalley, R. E.|year=1991|title=Fullerenes with metals inside|journal=The Journal of Physical Chemistry|volume=95|issue=20|pages=7564|DOI=10.1021/j100173a002}}</ref><ref>{{Cite journal|last=Muhr|first=H. -J.|last2=Nesper|first2=R.|last3=Schnyder|first3=B.|last4=Kötz|first4=R.|year=1996|title=The boron heterofullerenes C<sub>59</sub>B and C<sub>69</sub>B: Generation, extraction, mass spectrometric and XPS characterization|journal=Chemical Physics Letters|volume=249|issue=5–6|pages=399|bibcode=1996CPL...249..399M|DOI=10.1016/0009-2614(95)01451-9|PMID=}}</ref>、[[窒素]]（'''[[アザフラーレン]]'''）<ref>{{Cite journal|last=Averdung|first=J.|last2=Luftmann|first2=H.|last3=Schlachter|first3=I.|last4=Mattay|first4=J.|year=1995|title=Aza-dihydro[60]fullerene in the gas phase. A mass-spectrometric and quantumchemical study|journal=Tetrahedron|volume=51|issue=25|pages=6977|DOI=10.1016/0040-4020(95)00361-B|PMID=|PMC=}}</ref><ref>{{Cite journal|last=Lamparth|first=I.|last2=Nuber|first2=B.|last3=Schick|first3=G.|last4=Skiebe|first4=A.|last5=Grösser|first5=T.|last6=Hirsch|first6=A.|year=1995|title=C<sub>59</sub>N<sup>+</sup> and C<sub>69</sub>N<sup>+</sup>: Isoelectronic Heteroanalogues of C<sub>60</sub> and C<sub>70</sub>|journal=Angewandte Chemie International Edition in English|volume=34|issue=20|pages=2257|DOI=10.1002/anie.199522571|PMID=|PMC=}}</ref>、[[酸素]]<ref>{{Cite journal|last=Christian|first=J. F.|last2=Wan|first2=Z.|last3=Anderson|first3=S. L.|year=1992|title=O<sup>+</sup>+C<sub>60•</sub>C<sub>60</sub>O<sup>+</sup> production and decomposition, charge transfer, and formation of C<sub>59</sub>O<sup>+</sup>. Dopeyball or [CO@C<sub>58</sub>]<sup>+</sup>|journal=Chemical Physics Letters|volume=199|issue=3–4|pages=373|bibcode=1992CPL...199..373C|DOI=10.1016/0009-2614(92)80134-W|PMID=|PMC=}}</ref>、[[ヒ素]]、[[ゲルマニウム]]<ref>{{Cite journal|last=Ohtsuki|first=T.|last2=Ohno|first2=K.|last3=Shiga|first3=K.|last4=Kawazoe|first4=Y.|last5=Maruyama|first5=Y.|last6=Masumoto|first6=K.|year=1999|title=Formation of As- and Ge-doped heterofullerenes|journal=Physical Review B|volume=60|issue=3|pages=1531|bibcode=1999PhRvB..60.1531O|DOI=10.1103/PhysRevB.60.1531|PMID=|PMC=}}</ref>、[[リン]]<ref>{{Cite journal|last=Möschel, C.|last2=Jansen, M.|year=1999|title=Darstellung stabiler Phosphor-Heterofullerene im Hochfrequenzofen|journal=Z. Anorg. Allg. Chem.|volume=625|issue=2|pages=175–177|DOI=10.1002/(SICI)1521-3749(199902)625:2<175::AID-ZAAC175>3.0.CO;2-2}}</ref>、[[ケイ素]]<ref>{{Cite journal|year=1999|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|bibcode=1999JChPh.110.6927P|DOI=10.1063/1.478598}}</ref>、[[鉄]]、[[銅]]、[[ニッケル]]、[[ロジウム]]<ref>{{Cite journal|last=Branz|first=W.|last2=Billas|first2=I. M. L.|last3=Malinowski|first3=N.|last4=Tast|first4=F.|last5=Heinebrodt|first5=M.|last6=Martin|first6=T. P.|year=1998|title=Cage substitution in metal–fullerene clusters|journal=The Journal of Chemical Physics|volume=109|issue=9|pages=3425|bibcode=1998JChPh.109.3425B|DOI=10.1063/1.477410|PMID=|PMC=}}</ref>および[[イリジウム]]<ref name="Billas">{{Cite journal|year=1999|title=Experimental and computational studies of heterofullerenes|journal=Nanostructured Materials|volume=12|issue=5–8|pages=1071–1076|DOI=10.1016/S0965-9773(99)00301-3|PMID=|PMC=}}</ref>置換が報告されている。分離されたヘテロフラーレンに関する報告は、窒素<ref>{{Cite journal|last=Harris|first=D.J.|date=1993|title=Discovery of Nitroballs: Research in Fullerene Chemistry|url=http://www.usc.edu/CSSF/History/1993/CatWin_S05.html}}</ref><ref>{{Cite journal|last=Hummelen|first=J. C.|last2=Knight|first2=B.|last3=Pavlovich|first3=J.|last4=Gonzalez|first4=R.|last5=Wudl|first5=F.|year=1995|title=Isolation of the Heterofullerene C<sub>59</sub>N as Its Dimer (C<sub>59</sub>N)<sub>2</sub>|journal=Science|volume=269|issue=5230|pages=1554–1556|bibcode=1995Sci...269.1554H|DOI=10.1126/science.269.5230.1554|PMID=17789446|PMC=}}</ref><ref>{{Cite journal|last=Keshavarz-K|first=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.|year=1996|title=Synthesis of hydroazafullerene C<sub>59</sub>HN, the parent hydroheterofullerene|journal=Nature|volume=383|issue=6596|pages=147|bibcode=1996Natur.383..147K|DOI=10.1038/383147a0|PMID=|PMC=}}</ref><ref>{{Cite journal|last=Nuber|first=B.|last2=Hirsch|first2=A.|year=1996|title=A new route to nitrogen heterofullerenes and the first synthesis of (C<sub>69</sub>N)<sub>2</sub>|journal=Chemical Communications|issue=12|pages=1421|DOI=10.1039/CC9960001421|PMID=|PMC=}}</ref><ref>{{Cite journal|last=Zhang|first=G.|last2=Huang|first2=S.|last3=Xiao|first3=Z.|last4=Chen|first4=Q.|last5=Gan|first5=L.|last6=Wang|first6=Z.|year=2008|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|DOI=10.1021/ja805072h|PMID=18759401|PMC=}}</ref>および酸素に基づくものに限定されている<ref>{{Cite journal|last=Xin|first=N.|last2=Huang|first2=H.|last3=Zhang|first3=J.|last4=Dai|first4=Z.|last5=Gan|first5=L.|year=2012|title=Fullerene Doping: Preparation of Azafullerene C<sub>59</sub>NH and Oxafulleroids C<sub>59</sub>O<sub>3</sub> and C<sub>60</sub>O<sub>4</sub>|journal=Angewandte Chemie International Edition|volume=51|issue=25|pages=6163–6166|DOI=10.1002/anie.201202777|PMID=22573566|PMC=}}</ref>。
+'''ヘテロフラーレン''' (heterofullerene) は、[[炭素]]原子が非炭素原子で置換された[[フラーレン]]である。少なくとも1つの炭素原子が別の元素で置き換えられている<ref>{{Cite journal|last=Vostrowsky|first=O.|last2=Hirsch|first2=A.|year=2006|title=Heterofullerenes|journal=Chemical Reviews|volume=106|issue=12|pages=5191–5207|doi=10.1021/cr050561e|pmid=17165685|pmc=}}</ref><ref>{{Cite journal|last=Hummelen|first=Jan C.|last2=Bellavia-Lund|first2=Cheryl|last3=Wudl|first3=Fred|year=1999|title=Heterofullerenes. Fullerenes and Related Structures|url=|journal=Topics in Current Chemistry|volume=199|issue=|pages=93–134|doi=10.1007/3-540-68117-5_3}}</ref>。[[分光法]]に基づいて、[[ホウ素]]（'''[[ボラフラーレン]]'''）<ref>{{Cite journal|last=Chai, Y.|last2=Guo, T.|last3=Jin, C.|last4=Haufler, R. E.|last5=Chibante, L. P. F.|last6=Fure, J.|last7=Wang, L.|last8=Alford, J. M.|last9=Smalley, R. E.|year=1991|title=Fullerenes with metals inside|journal=The Journal of Physical Chemistry|volume=95|issue=20|pages=7564|doi=10.1021/j100173a002}}</ref><ref>{{Cite journal|last=Muhr|first=H. -J.|last2=Nesper|first2=R.|last3=Schnyder|first3=B.|last4=Kötz|first4=R.|year=1996|title=The boron heterofullerenes C<sub>59</sub>B and C<sub>69</sub>B: Generation, extraction, mass spectrometric and XPS characterization|journal=Chemical Physics Letters|volume=249|issue=5–6|pages=399|bibcode=1996CPL...249..399M|doi=10.1016/0009-2614(95)01451-9|pmid=}}</ref>、[[窒素]]（'''[[アザフラーレン]]'''）<ref>{{Cite journal|last=Averdung|first=J.|last2=Luftmann|first2=H.|last3=Schlachter|first3=I.|last4=Mattay|first4=J.|year=1995|title=Aza-dihydro[60]fullerene in the gas phase. A mass-spectrometric and quantumchemical study|journal=Tetrahedron|volume=51|issue=25|pages=6977|doi=10.1016/0040-4020(95)00361-B|pmid=|pmc=}}</ref><ref>{{Cite journal|last=Lamparth|first=I.|last2=Nuber|first2=B.|last3=Schick|first3=G.|last4=Skiebe|first4=A.|last5=Grösser|first5=T.|last6=Hirsch|first6=A.|year=1995|title=C<sub>59</sub>N<sup>+</sup> and C<sub>69</sub>N<sup>+</sup>: Isoelectronic Heteroanalogues of C<sub>60</sub> and C<sub>70</sub>|journal=Angewandte Chemie International Edition in English|volume=34|issue=20|pages=2257|doi=10.1002/anie.199522571|pmid=|pmc=}}</ref>、[[酸素]]<ref>{{Cite journal|last=Christian|first=J. F.|last2=Wan|first2=Z.|last3=Anderson|first3=S. L.|year=1992|title=O<sup>+</sup>+C<sub>60•</sub>C<sub>60</sub>O<sup>+</sup> production and decomposition, charge transfer, and formation of C<sub>59</sub>O<sup>+</sup>. Dopeyball or [CO@C<sub>58</sub>]<sup>+</sup>|journal=Chemical Physics Letters|volume=199|issue=3–4|pages=373|bibcode=1992CPL...199..373C|doi=10.1016/0009-2614(92)80134-W|pmid=|pmc=}}</ref>、[[ヒ素]]、[[ゲルマニウム]]<ref>{{Cite journal|last=Ohtsuki|first=T.|last2=Ohno|first2=K.|last3=Shiga|first3=K.|last4=Kawazoe|first4=Y.|last5=Maruyama|first5=Y.|last6=Masumoto|first6=K.|year=1999|title=Formation of As- and Ge-doped heterofullerenes|journal=Physical Review B|volume=60|issue=3|pages=1531|bibcode=1999PhRvB..60.1531O|doi=10.1103/PhysRevB.60.1531|pmid=|pmc=}}</ref>、[[リン]]<ref>{{Cite journal|last=Möschel, C.|last2=Jansen, M.|year=1999|title=Darstellung stabiler Phosphor-Heterofullerene im Hochfrequenzofen|journal=Z. Anorg. Allg. 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C.|last2=Knight|first2=B.|last3=Pavlovich|first3=J.|last4=Gonzalez|first4=R.|last5=Wudl|first5=F.|year=1995|title=Isolation of the Heterofullerene C<sub>59</sub>N as Its Dimer (C<sub>59</sub>N)<sub>2</sub>|journal=Science|volume=269|issue=5230|pages=1554–1556|bibcode=1995Sci...269.1554H|doi=10.1126/science.269.5230.1554|pmid=17789446|pmc=}}</ref><ref>{{Cite journal|last=Keshavarz-K|first=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. 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 == 出典 ==