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Synthesis, isolation, and X-ray structural characterization of trifluoromethylated C78 fullerenes: C78(2)(CF3)10/12 and C78 (3)(CF3)12/14

https://doi.org/10.17586/2220-8054-2016-7-1-111-117

Abstract

Four CF3 derivatives of C78, C78(2)(CF3)10/12 and C78(3)(CF3)12/14, have been isolated via HPLC from the products of high-temperature trifluoromethylation of a C76–C96 fullerene mixture or a C78 fraction. Their molecular structures were determined by single crystal X-ray crystallography using synchrotron radiation. The addition patterns of the new compounds are compared with each other and with the previously known C78(2)(CF3)10 and C78(3)(CF3)12.

About the Authors

N. B. Tamm
Department of Chemistry, Moscow State University
Russian Federation

Moscow



M. P. Kosaya
Department of Chemistry, Moscow State University
Russian Federation

Moscow



M. A. Fritz
Department of Chemistry, Moscow State University
Russian Federation

Moscow



S. I. Troyanov
Department of Chemistry, Moscow State University
Russian Federation

Moscow



References

1. Yoshida M., Aihara J. 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., 1999, 1, P. 227–230.

2. Fowler P.W., Manolopoulos D.E. An Atlas of Fullerenes. Clarendon, Oxford, 1995, 392 p.

3. Diederich F., Whetten R.L., et al. Fullerene Isomerism: Isolation of C2v–C78 and D3–C78. Science, 1991, 254, P. 1768–1770.

4. Wakabayashi T., Kikuchi K., et al. Pressure-Controlled Selective Isomer Formation of Fullerene C78. J. Phys. Chem., 1994, 98, P. 3090–3091.

5. Shustova N.B., Newell B.S., et al. 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., 2007, 46, P. 4111–4114.

6. Herrmann A., Diederich F. Synthesis, separation and characterisation of the first pure multiple adducts of C2v- and D3–C78. J. Chem. Soc., Perkin Trans. 2, 1997, P. 1679–1684.

7. Han A.H., Wakahara T., et al. A new method for separating the D3 and C2v isomers of C78. New J. Chem., 2009, 33, P. 497–500.

8. Troyanov S.I., Kemnitz E. The first crystal structure of a halogenated higher fullerene, C78Br18, obtained by bromination of a fullerene mixture. Eur. J. Org. Chem., 2003, P. 3916–3919.

9. Simeonov K.S., Amsharov K.Yu., Jansen M. Chlorinated derivatives of C78-fullerene isomers with unusually short intermolecular halogen-halogen contacts. Chem.-Eur. J., 2008, 14, P. 9585–9590.

10. Simeonov K.S., Amsharov K.Yu., Krokos E., Jansen M. An epilogue on the C78-fullerene family: The discovery and characterization of an elusive isomer. Angew. Chem. Int. Ed., 2008, 47, P. 6283–6285.

11. Burtsev A.V., Kemnitz E., Troyanov S.I. Synthesis and structure of fullerene halides C70X10(X= Br, Cl) and C78Cl18. Crystallogr. Rep., 2008, 53, P. 639–644.

12. Troyanov S.I., Tamm N.B., et al. Synthesis and structure of a highly chlorinated C78: C78(2)Cl30. Z. Anorg. Allg. Chem., 2009, 635, P. 1783–1786.

13. Kemnitz E., Troyanov S.I. Chlorides of isomeric C78 fullerenes: C78(1)Cl30, C78(2)Cl30, and C78(2)Cl18. Mendeleev Commun., 2010, 20, P. 74–76.

14. Kareev I.E., Popov A.A., et al. 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., 2008, 130, P. 13471–13489.

15. Tamm N.B., Troyanov S.I. Isomer C78(2) captured as the perfluoroethyl derivative C78(C2F5)10. Mendeleev Commun., 2009, 19, P. 198–199.

16. Chang K., Fritz M.A., et al. Synthesis, structure, and theoretical study of trifluoromethyl derivatives of C84(22) fullerene. Chem. -Eur. J., 2013, 19, P. 578–587.

17. Romanova N.A., Fritz M.A., et al. Synthesis, structure, and theoretical study of trifluoromethyl derivatives of C84(23) fullerene. Chem. -Eur. J., 2013, 19, P. 11707–11716.

18. Romanova N.A., Fritz M.A., et al. Synthesis and structure of trifluoromethyl derivatives of fullerenes C84(16) and C84(18). Russ. Chem. Bull. Int. Ed., 2014, 63, P. 2657–2667.

19. Kareev I.E., Shustova N.B., et al. Thermally stable perfluoroalkylfullerenes with the skew-pentagonal-pyramid pattern: C60(C2F5)4O, C60(CF3)4O, and C60(CF3)6. J. Am. Chem. Soc., 2006, 128, P. 12268–12280.

20. Sheldrick G.M. A short history of SHELX. Acta Crystallogr. A, 2008, 64, P. 112–122.

21. Yang S., Wei T., Kemnitz E., Troyanov S.I. The most stable isomer of C88 fullerene, Cs–C88(17), revealed by X-ray structures of C88Cl16 and C88Cl22. Chem. Asian J., 2012, 7, P. 290–293.


Review

For citations:


Tamm N.B., Kosaya M.P., Fritz M.A., Troyanov S.I. Synthesis, isolation, and X-ray structural characterization of trifluoromethylated C78 fullerenes: C78(2)(CF3)10/12 and C78 (3)(CF3)12/14. Nanosystems: Physics, Chemistry, Mathematics. 2016;7(1):111-117. https://doi.org/10.17586/2220-8054-2016-7-1-111-117

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