<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE article PUBLIC "-//NLM//DTD JATS (Z39.96) Journal Publishing DTD v1.3 20210610//EN" "JATS-journalpublishing1-3.dtd">
<article article-type="research-article" dtd-version="1.3" xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xml:lang="en"><front><journal-meta><journal-id journal-id-type="publisher-id">najo</journal-id><journal-title-group><journal-title xml:lang="en">Nanosystems: Physics, Chemistry, Mathematics</journal-title><trans-title-group xml:lang="ru"><trans-title>Наносистемы: физика, химия, математика</trans-title></trans-title-group></journal-title-group><issn pub-type="ppub">2220-8054</issn><issn pub-type="epub">2305-7971</issn><publisher><publisher-name>Университет ИТМО</publisher-name></publisher></journal-meta><article-meta><article-id custom-type="elpub" pub-id-type="custom">najo-868</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Article</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="en"><subject>FULLERENS</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="ru"><subject>FULLERENS</subject></subj-group></article-categories><title-group><article-title>Synthesis, isolation, and X-ray structural characterization of trifluoromethylated C90 fullerenes: C90(30)(CF3)18 and C90(35)(CF3)14</article-title><trans-title-group xml:lang="ru"><trans-title></trans-title></trans-title-group></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="western" xml:lang="en"><surname>Tamm</surname><given-names>N. B.</given-names></name></name-alternatives><bio xml:lang="en"><p>Department of Chemistry</p><p>Moscow</p></bio><email xlink:type="simple">tamm@thermo.chem.msu.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="western" xml:lang="en"><surname>Troyanov</surname><given-names>S. I.</given-names></name></name-alternatives><bio xml:lang="en"><p>Department of Chemistry</p><p>Moscow</p></bio><email xlink:type="simple">stroyano@thermo.chem.msu.ru</email><xref ref-type="aff" rid="aff-1"/></contrib></contrib-group><aff xml:lang="en" id="aff-1"><institution>Moscow State University</institution><country>Russian Federation</country></aff><pub-date pub-type="collection"><year>2014</year></pub-date><pub-date pub-type="epub"><day>15</day><month>08</month><year>2025</year></pub-date><volume>5</volume><issue>1</issue><fpage>39</fpage><lpage>45</lpage><permissions><copyright-statement>Copyright &amp;#x00A9; Tamm N.B., Troyanov S.I., 2025</copyright-statement><copyright-year>2025</copyright-year><copyright-holder xml:lang="ru">Tamm N.B., Troyanov S.I.</copyright-holder><copyright-holder xml:lang="en">Tamm N.B., Troyanov S.I.</copyright-holder><license xml:lang="ru" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>Данная работа распространяется под лицензией Creative Commons Attribution 4.0.</license-p></license><license xml:lang="en" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>This work is licensed under a Creative Commons Attribution 4.0 License.</license-p></license></permissions><self-uri xlink:href="https://nanojournal.ifmo.ru/jour/article/view/868">https://nanojournal.ifmo.ru/jour/article/view/868</self-uri><abstract><p>Two CF3 derivatives of C90, C90(30)(CF3)18 and C90(35)(CF3)14, have been isolated via HPLC from the products of a high-temperature trifluoromethylation of a C76–C96 fullerene mixture with CF3I. Their molecular structures were determined by single crystal X-ray crystallography using synchrotron radiation. The addition patterns of the new compounds are discussed in comparison with those of the corresponding chlorinated C90.</p></abstract><kwd-group xml:lang="en"><kwd>Fullerenes</kwd><kwd>C90</kwd><kwd>Trifluoromethylation</kwd><kwd>HPLC</kwd><kwd>Structure elucidation</kwd></kwd-group><funding-group><funding-statement xml:lang="en">This work was supported in part by the Russian Foundation for Basic Research (grants 12-03-00324 and 13-03-91332).</funding-statement></funding-group></article-meta></front><back><ref-list><title>References</title><ref id="cit1"><label>1</label><citation-alternatives><mixed-citation xml:lang="ru">P.W. Fowler, D.E. Manolopoulos. An Atlas of Fullerenes, Clarendon, Oxford, 392 p. (1995).</mixed-citation><mixed-citation xml:lang="en">P.W. Fowler, D.E. Manolopoulos. An Atlas of Fullerenes, Clarendon, Oxford, 392 p. (1995).</mixed-citation></citation-alternatives></ref><ref id="cit2"><label>2</label><citation-alternatives><mixed-citation xml:lang="ru">T.J.S. Dennis, T. Kai, K. Asato, T. Tomiyama, H. Shinohara, T. Yoshida, Y. Kobayashi, H. Ishiwatari, Y. Miyake, K. Kikuchi, Y. Achiba. Isolation and characterization by 13C NMR spectroscopy of [84]fullerene minor isomers. J. Phys. Chem. A, 103, P. 8747–8752 (1999).</mixed-citation><mixed-citation xml:lang="en">T.J.S. Dennis, T. Kai, K. Asato, T. Tomiyama, H. Shinohara, T. Yoshida, Y. Kobayashi, H. Ishiwatari, Y. Miyake, K. Kikuchi, Y. Achiba. Isolation and characterization by 13C NMR spectroscopy of [84]fullerene minor isomers. J. Phys. Chem. A, 103, P. 8747–8752 (1999).</mixed-citation></citation-alternatives></ref><ref id="cit3"><label>3</label><citation-alternatives><mixed-citation xml:lang="ru">Y. Miyake, T. Minami, K. Kikuchi, M. Kainosho, Y. Achiba. Trends in structure and growth of higher fullerenes isomer structure of C86 and C88. Mol. Cryst. Liq. Cryst., 340, P. 553–558 (2000).</mixed-citation><mixed-citation xml:lang="en">Y. Miyake, T. Minami, K. Kikuchi, M. Kainosho, Y. Achiba. Trends in structure and growth of higher fullerenes isomer structure of C86 and C88. Mol. Cryst. Liq. Cryst., 340, P. 553–558 (2000).</mixed-citation></citation-alternatives></ref><ref id="cit4"><label>4</label><citation-alternatives><mixed-citation xml:lang="ru">N.B. Shustova, B.N. Newell, S.M. Miller, O.P. Anderson, R.D. Bolskar, K. Seppelt, A.A. Popov, O.V. Boltalina, S.H. Strauss. Discovering and verifying elusive fullerene cage isomers: structures of C2-p11-(C74-D3h)(CF3)12 and C2-p11-(C78-D3h(5))(CF3)12. Angew. Chem. Int. Ed., 46, P. 4111–4114 (2007).</mixed-citation><mixed-citation xml:lang="en">N.B. Shustova, B.N. Newell, S.M. Miller, O.P. Anderson, R.D. Bolskar, K. Seppelt, A.A. Popov, O.V. Boltalina, S.H. Strauss. Discovering and verifying elusive fullerene cage isomers: structures of C2-p11-(C74-D3h)(CF3)12 and C2-p11-(C78-D3h(5))(CF3)12. Angew. Chem. Int. Ed., 46, P. 4111–4114 (2007).</mixed-citation></citation-alternatives></ref><ref id="cit5"><label>5</label><citation-alternatives><mixed-citation xml:lang="ru">K.S. Simeonov, K.Yu. Amsharov, M. Jansen. Connectivity of the chiral D2-symmetric isomer of C76 through a crystal structure determination of C76Cl18·TiCl4. Angew. Chem. Int. Ed., 46, P. 8419–8421 (2007).</mixed-citation><mixed-citation xml:lang="en">K.S. Simeonov, K.Yu. Amsharov, M. Jansen. Connectivity of the chiral D2-symmetric isomer of C76 through a crystal structure determination of C76Cl18·TiCl4. Angew. Chem. Int. Ed., 46, P. 8419–8421 (2007).</mixed-citation></citation-alternatives></ref><ref id="cit6"><label>6</label><citation-alternatives><mixed-citation xml:lang="ru">E. Kemnitz, S.I. Troyanov. Chlorides of isomeric C78 fullerenes: C78(1)Cl30, C78(2)Cl30, and C78(2)Cl18. Mendeleev Commun., 20, P. 74–76 (2010).</mixed-citation><mixed-citation xml:lang="en">E. Kemnitz, S.I. Troyanov. Chlorides of isomeric C78 fullerenes: C78(1)Cl30, C78(2)Cl30, and C78(2)Cl18. Mendeleev Commun., 20, P. 74–76 (2010).</mixed-citation></citation-alternatives></ref><ref id="cit7"><label>7</label><citation-alternatives><mixed-citation xml:lang="ru">K.S. Simeonov, K.Yu. Amsharov, M. Jansen. C80Cl12 — a chlorinated derivative of the chiral D2−C80 isomer: empirical rationale of halogen atoms addition pattern. Chem.–Eur. J., 15, P. 1812–1815 (2009).</mixed-citation><mixed-citation xml:lang="en">K.S. Simeonov, K.Yu. Amsharov, M. Jansen. C80Cl12 — a chlorinated derivative of the chiral D2−C80 isomer: empirical rationale of halogen atoms addition pattern. Chem.–Eur. J., 15, P. 1812–1815 (2009).</mixed-citation></citation-alternatives></ref><ref id="cit8"><label>8</label><citation-alternatives><mixed-citation xml:lang="ru">S.I. Troyanov, N.B. Tamm. Crystal and molecular structures of trifluoromethyl derivatives of C82 fullerene: C82(CF3)12 and C82(CF3)18. Crystallogr. Rep., 55, P. 432–435 (2010).</mixed-citation><mixed-citation xml:lang="en">S.I. Troyanov, N.B. Tamm. Crystal and molecular structures of trifluoromethyl derivatives of C82 fullerene: C82(CF3)12 and C82(CF3)18. Crystallogr. Rep., 55, P. 432–435 (2010).</mixed-citation></citation-alternatives></ref><ref id="cit9"><label>9</label><citation-alternatives><mixed-citation xml:lang="ru">N.B. Tamm, L.N. Sidorov, E. Kemnitz, S.I. Troyanov. Isolation and structural X-ray investigation of perfluoroalkyl derivatives of six cage isomers of C84. Chem.–Eur. J., 15, P. 10486-10492 (2009).</mixed-citation><mixed-citation xml:lang="en">N.B. Tamm, L.N. Sidorov, E. Kemnitz, S.I. Troyanov. Isolation and structural X-ray investigation of perfluoroalkyl derivatives of six cage isomers of C84. Chem.–Eur. J., 15, P. 10486-10492 (2009).</mixed-citation></citation-alternatives></ref><ref id="cit10"><label>10</label><citation-alternatives><mixed-citation xml:lang="ru">S.I. Troyanov, N.B. Tamm. Crystal and molecular structures of trifluoromethyl derivatives of fullerene C86, C86(CF3)16 and C86(CF3)18. Crystallogr. Rep., 54, P. 598–602 (2009).</mixed-citation><mixed-citation xml:lang="en">S.I. Troyanov, N.B. Tamm. Crystal and molecular structures of trifluoromethyl derivatives of fullerene C86, C86(CF3)16 and C86(CF3)18. Crystallogr. Rep., 54, P. 598–602 (2009).</mixed-citation></citation-alternatives></ref><ref id="cit11"><label>11</label><citation-alternatives><mixed-citation xml:lang="ru">S.I. Troyanov, N.B. Tamm. Cage connectivities of C88 (33) and C92 (82) fullerenes captured as trifluoromethyl derivatives, C88(CF3)18 and C92(CF3)16. Chem. Commun., P. 6035–6037 (2009).</mixed-citation><mixed-citation xml:lang="en">S.I. Troyanov, N.B. Tamm. Cage connectivities of C88 (33) and C92 (82) fullerenes captured as trifluoromethyl derivatives, C88(CF3)18 and C92(CF3)16. Chem. Commun., P. 6035–6037 (2009).</mixed-citation></citation-alternatives></ref><ref id="cit12"><label>12</label><citation-alternatives><mixed-citation xml:lang="ru">S. Yang, T. Wei, E. Kemnitz, S.I. Troyanov. Four isomers of C96 fullerene structurally proven as C96Cl22 and C96Cl24. Angew. Chem. Int. Ed., 51, P. 8239–8242 (2012).</mixed-citation><mixed-citation xml:lang="en">S. Yang, T. Wei, E. Kemnitz, S.I. Troyanov. Four isomers of C96 fullerene structurally proven as C96Cl22 and C96Cl24. Angew. Chem. Int. Ed., 51, P. 8239–8242 (2012).</mixed-citation></citation-alternatives></ref><ref id="cit13"><label>13</label><citation-alternatives><mixed-citation xml:lang="ru">M. Yoshida, J. Aihara. Validity of the weighted HOMO–LUMO energy separation as an index of kinetic stability for fullerenes with up to 120 carbon atoms. Phys. Chem. Chem. Phys., 1, P. 227–230 (1999).</mixed-citation><mixed-citation xml:lang="en">M. Yoshida, J. Aihara. Validity of the weighted HOMO–LUMO energy separation as an index of kinetic stability for fullerenes with up to 120 carbon atoms. Phys. Chem. Chem. Phys., 1, P. 227–230 (1999).</mixed-citation></citation-alternatives></ref><ref id="cit14"><label>14</label><citation-alternatives><mixed-citation xml:lang="ru">Y. Achiba, K. Kikuchi, Y. Aihara, T. Wakabayashi, Y. Miyake, M. Kainosho. Higher Fullerenes: Structure and Properties. Proceedings of “Science and Technology of Fullerene Materials” MRS Symposia, Pittsburgh, P. Bernier, et al. (Eds.), 359, P. 3–9 (1995).</mixed-citation><mixed-citation xml:lang="en">Y. Achiba, K. Kikuchi, Y. Aihara, T. Wakabayashi, Y. Miyake, M. Kainosho. Higher Fullerenes: Structure and Properties. Proceedings of “Science and Technology of Fullerene Materials” MRS Symposia, Pittsburgh, P. Bernier, et al. (Eds.), 359, P. 3–9 (1995).</mixed-citation></citation-alternatives></ref><ref id="cit15"><label>15</label><citation-alternatives><mixed-citation xml:lang="ru">Y. Achiba, K. Kikuchi, Y. Aihara, T. Wakabayashi, Y. Miyake, M. Kainosho. Trends in Large Fullerenes: Are They Balls or Tubes. The Chemical Physics of Fullerenes 10 (and 5) Years Later. Proceedings of the NATO Advanced Research Workshop, Varenna, Italy, June 12-16, 1995. Andreoni, W., Ed., Kluwer Academic Publishers: Dordrecht, Netherlands, P. 139–147 (1996).</mixed-citation><mixed-citation xml:lang="en">Y. Achiba, K. Kikuchi, Y. Aihara, T. Wakabayashi, Y. Miyake, M. Kainosho. Trends in Large Fullerenes: Are They Balls or Tubes. The Chemical Physics of Fullerenes 10 (and 5) Years Later. Proceedings of the NATO Advanced Research Workshop, Varenna, Italy, June 12-16, 1995. Andreoni, W., Ed., Kluwer Academic Publishers: Dordrecht, Netherlands, P. 139–147 (1996).</mixed-citation></citation-alternatives></ref><ref id="cit16"><label>16</label><citation-alternatives><mixed-citation xml:lang="ru">G. Sun. Theoretical 13C NMR chemical shifts of the stable isomers of fullerene C90. Chem. Phys., 289, P. 371–380 (2003).</mixed-citation><mixed-citation xml:lang="en">G. Sun. Theoretical 13C NMR chemical shifts of the stable isomers of fullerene C90. Chem. Phys., 289, P. 371–380 (2003).</mixed-citation></citation-alternatives></ref><ref id="cit17"><label>17</label><citation-alternatives><mixed-citation xml:lang="ru">H. Yang, C.M. Beavers, Z. Wang, A. Jiang, Z. Liu, H. Jin, B.Q. Mercado, M.M. Olmstead, A.L. Balch. Isolation of a small carbon nanotube: the surprising appearance of D5h(1)−C90. Angew. Chem. Int. Ed., 49, P. 886–890 (2010).</mixed-citation><mixed-citation xml:lang="en">H. Yang, C.M. Beavers, Z. Wang, A. Jiang, Z. Liu, H. Jin, B.Q. Mercado, M.M. Olmstead, A.L. Balch. Isolation of a small carbon nanotube: the surprising appearance of D5h(1)−C90. Angew. Chem. Int. Ed., 49, P. 886–890 (2010).</mixed-citation></citation-alternatives></ref><ref id="cit18"><label>18</label><citation-alternatives><mixed-citation xml:lang="ru">H. Yang, B.Q. Mercado, H. Jin, Z. Wang, A. Jiang, Z. Liu, C.M. Beavers, M.M. Olmstead, A.L. Balch. Isolation and crystallographic identification of four isomers of Sm@C90. Chem. Commun., 47, P. 2068– 2070 (2011).</mixed-citation><mixed-citation xml:lang="en">H. Yang, B.Q. Mercado, H. Jin, Z. Wang, A. Jiang, Z. Liu, C.M. Beavers, M.M. Olmstead, A.L. Balch. Isolation and crystallographic identification of four isomers of Sm@C90. Chem. Commun., 47, P. 2068– 2070 (2011).</mixed-citation></citation-alternatives></ref><ref id="cit19"><label>19</label><citation-alternatives><mixed-citation xml:lang="ru">I.E. Kareev, A.A. Popov, I.V. Kuvychko, N.B. Shustova, S.F. Lebedkin, V.P. Bubnov, O.P. Anderson, K. Seppelt, S.H. Strauss, O.V. Boltalina. Synthesis and X-ray or NMR/DFT structure elucidation of twenty-one new trifluoromethyl derivatives of soluble cage isomers of C76, C78, C84, and C90. J. Am. Chem. Soc., 130, P. 13471–13489 (2008).</mixed-citation><mixed-citation xml:lang="en">I.E. Kareev, A.A. Popov, I.V. Kuvychko, N.B. Shustova, S.F. Lebedkin, V.P. Bubnov, O.P. Anderson, K. Seppelt, S.H. Strauss, O.V. Boltalina. Synthesis and X-ray or NMR/DFT structure elucidation of twenty-one new trifluoromethyl derivatives of soluble cage isomers of C76, C78, C84, and C90. J. Am. Chem. Soc., 130, P. 13471–13489 (2008).</mixed-citation></citation-alternatives></ref><ref id="cit20"><label>20</label><citation-alternatives><mixed-citation xml:lang="ru">E. Kemnitz, S.I. Troyanov. Connectivity patterns of two C90 isomers provided by the structure elucidation of C90Cl32. Angew. Chem. Int. Ed., 48, P. 2584–2587 (2009).</mixed-citation><mixed-citation xml:lang="en">E. Kemnitz, S.I. Troyanov. Connectivity patterns of two C90 isomers provided by the structure elucidation of C90Cl32. Angew. Chem. Int. Ed., 48, P. 2584–2587 (2009).</mixed-citation></citation-alternatives></ref><ref id="cit21"><label>21</label><citation-alternatives><mixed-citation xml:lang="ru">S.I. Troyanov, S. Yang, C. Chen, E. Kemnitz. Six IPR isomers of C90 fullerene captured as chlorides: Carbon cage connectivities and chlorination patterns. Chem.–Eur. J., 17, P. 10622–10669 (2011).</mixed-citation><mixed-citation xml:lang="en">S.I. Troyanov, S. Yang, C. Chen, E. Kemnitz. Six IPR isomers of C90 fullerene captured as chlorides: Carbon cage connectivities and chlorination patterns. Chem.–Eur. J., 17, P. 10622–10669 (2011).</mixed-citation></citation-alternatives></ref><ref id="cit22"><label>22</label><citation-alternatives><mixed-citation xml:lang="ru">www.mercorp.com</mixed-citation><mixed-citation xml:lang="en">www.mercorp.com</mixed-citation></citation-alternatives></ref><ref id="cit23"><label>23</label><citation-alternatives><mixed-citation xml:lang="ru">K. Chang, M.A. Fritz, N.B. Tamm, A.A. Goryunkov, L.N. Sidorov, C. Chen, S. Yang, E. Kemnitz, S.I. Troyanov. Synthesis, structure, and theoretical study of trifluoromethyl derivatives of C84(22) fullerene. Chem.–Eur. J., 19, P. 578-587 (2013).</mixed-citation><mixed-citation xml:lang="en">K. Chang, M.A. Fritz, N.B. Tamm, A.A. Goryunkov, L.N. Sidorov, C. Chen, S. Yang, E. Kemnitz, S.I. Troyanov. Synthesis, structure, and theoretical study of trifluoromethyl derivatives of C84(22) fullerene. Chem.–Eur. J., 19, P. 578-587 (2013).</mixed-citation></citation-alternatives></ref><ref id="cit24"><label>24</label><citation-alternatives><mixed-citation xml:lang="ru">D.V. Ignat’eva, A.A. Goryunkov, N.B. Tamm, I.N. Ioffe, L.N. Sidorov, S.I. Troyanov. Isolation and structural characterization of the most highly trifluoromethylated C70 fullerenes: C70(CF3)18 and C70(CF3)20. New J. Chem., 37, P. 299-302 (2013).</mixed-citation><mixed-citation xml:lang="en">D.V. Ignat’eva, A.A. Goryunkov, N.B. Tamm, I.N. Ioffe, L.N. Sidorov, S.I. Troyanov. Isolation and structural characterization of the most highly trifluoromethylated C70 fullerenes: C70(CF3)18 and C70(CF3)20. New J. Chem., 37, P. 299-302 (2013).</mixed-citation></citation-alternatives></ref><ref id="cit25"><label>25</label><citation-alternatives><mixed-citation xml:lang="ru">M.A. Lanskikh, K. Chang, N.B. Tamm, E. Kemnitz, S.I. Troyanov. Trifluoromethyl derivatives of C88(33) fullerene. Mendeleev Commun., 22, P. 136–137 (2012).</mixed-citation><mixed-citation xml:lang="en">M.A. Lanskikh, K. Chang, N.B. Tamm, E. Kemnitz, S.I. Troyanov. Trifluoromethyl derivatives of C88(33) fullerene. Mendeleev Commun., 22, P. 136–137 (2012).</mixed-citation></citation-alternatives></ref><ref id="cit26"><label>26</label><citation-alternatives><mixed-citation xml:lang="ru">N.B. Tamm, L.N. Sidorov, E. Kemnitz, S.I. Troyanov. Crystal structures of C94(CF3)20 and C96(C2F5)12 reveal the cage connectivities in C94 (61) and C96 (145) fullerenes. Angew. Chem. Int. Ed., 48, P. 9102– 9104 (2009).</mixed-citation><mixed-citation xml:lang="en">N.B. Tamm, L.N. Sidorov, E. Kemnitz, S.I. Troyanov. Crystal structures of C94(CF3)20 and C96(C2F5)12 reveal the cage connectivities in C94 (61) and C96 (145) fullerenes. Angew. Chem. Int. Ed., 48, P. 9102– 9104 (2009).</mixed-citation></citation-alternatives></ref><ref id="cit27"><label>27</label><citation-alternatives><mixed-citation xml:lang="ru">H. Liang, Y.-Z. Tan, T. Zhou, Z.-L. Chen, S.-Y. Xie, R.-B. Huang, L.-S. Zheng. C76Cl34: High chlorination of the inherent chiral fullerene with a helical configuration. Inorg. Chem., 49, P. 3089–3091 (2010).</mixed-citation><mixed-citation xml:lang="en">H. Liang, Y.-Z. Tan, T. Zhou, Z.-L. Chen, S.-Y. Xie, R.-B. Huang, L.-S. Zheng. C76Cl34: High chlorination of the inherent chiral fullerene with a helical configuration. Inorg. Chem., 49, P. 3089–3091 (2010).</mixed-citation></citation-alternatives></ref><ref id="cit28"><label>28</label><citation-alternatives><mixed-citation xml:lang="ru">I.N. Ioffe, O.N. Mazaleva, C. Chen, S.-F. Yang, E. Kemnitz, S.I. Troyanov. C76 fullerene chlorides and cage transformations. Structural and theoretical study. Dalton Trans., 40, P. 11005–11011 (2011).</mixed-citation><mixed-citation xml:lang="en">I.N. Ioffe, O.N. Mazaleva, C. Chen, S.-F. Yang, E. Kemnitz, S.I. Troyanov. C76 fullerene chlorides and cage transformations. Structural and theoretical study. Dalton Trans., 40, P. 11005–11011 (2011).</mixed-citation></citation-alternatives></ref><ref id="cit29"><label>29</label><citation-alternatives><mixed-citation xml:lang="ru">S.M. Avdoshenko, A.A. Goryunkov, I.N. Ioffe, D.V. Ignat‘eva, L.N. Sidorov, P. Pattison, E. Kemnitz, S.I. Troyanov. Preparation, crystallographic characterization and theoretical study of C70(CF3)16 and C70(CF3)18. Chem. Commun., P. 2463–2465 (2006).</mixed-citation><mixed-citation xml:lang="en">S.M. Avdoshenko, A.A. Goryunkov, I.N. Ioffe, D.V. Ignat‘eva, L.N. Sidorov, P. Pattison, E. Kemnitz, S.I. Troyanov. Preparation, crystallographic characterization and theoretical study of C70(CF3)16 and C70(CF3)18. Chem. Commun., P. 2463–2465 (2006).</mixed-citation></citation-alternatives></ref><ref id="cit30"><label>30</label><citation-alternatives><mixed-citation xml:lang="ru">S.I. Troyanov, A.A. Popov. A [70]fullerene chloride, C70Cl16, obtained by the attempted bromination of C70 in TiCl4. Angew. Chem. Int. Ed., 44, P. 4215–4218 (2005).</mixed-citation><mixed-citation xml:lang="en">S.I. Troyanov, A.A. Popov. A [70]fullerene chloride, C70Cl16, obtained by the attempted bromination of C70 in TiCl4. Angew. Chem. Int. Ed., 44, P. 4215–4218 (2005).</mixed-citation></citation-alternatives></ref><ref id="cit31"><label>31</label><citation-alternatives><mixed-citation xml:lang="ru">N.B. Tamm, S.I. Troyanov. Trifluoromethyl derivatives of fullerene C76, C76(CF3)14−18. Mendeleev Commun., 20, P. 229–230 (2010).</mixed-citation><mixed-citation xml:lang="en">N.B. Tamm, S.I. Troyanov. Trifluoromethyl derivatives of fullerene C76, C76(CF3)14−18. Mendeleev Commun., 20, P. 229–230 (2010).</mixed-citation></citation-alternatives></ref><ref id="cit32"><label>32</label><citation-alternatives><mixed-citation xml:lang="ru">Z. Slanina, X. Zhao, S.-L. Lee, E. Osawa. Computations on the IPR isomers of C ˜ 88 and C90. Scr. Mater. 43, P. 733–741 (2000).</mixed-citation><mixed-citation xml:lang="en">Z. Slanina, X. Zhao, S.-L. Lee, E. Osawa. Computations on the IPR isomers of C ˜ 88 and C90. Scr. Mater. 43, P. 733–741 (2000).</mixed-citation></citation-alternatives></ref><ref id="cit33"><label>33</label><citation-alternatives><mixed-citation xml:lang="ru">M. Watanabe, D. Ishimaru, N. Mizorogi, M. Kiuchi, J. Aihara. Thermodynamically and kinetically stable isomers of the C88 and C90 fullerenes. J. Mol. Struct., - THEOCHEM, 726, P. 11–16 (2005).</mixed-citation><mixed-citation xml:lang="en">M. Watanabe, D. Ishimaru, N. Mizorogi, M. Kiuchi, J. Aihara. Thermodynamically and kinetically stable isomers of the C88 and C90 fullerenes. J. Mol. Struct., - THEOCHEM, 726, P. 11–16 (2005).</mixed-citation></citation-alternatives></ref></ref-list><fn-group><fn fn-type="conflict"><p>The authors declare that there are no conflicts of interest present.</p></fn></fn-group></back></article>
