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DOI: 10.1039/A907606I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1999, 2659-2666

Isolation and characterisation of fluorinated derivatives of [76]- and [78]fullerenes

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Ala’a K. Abdul-Sada, Tigran V. Avakyan, Olga V. Boltalina, Vitaly Yu. Markov, Joan M. Street and Roger Taylor

Abstract

From the fluorination of [76]fullerene with MnF3 at 450–500 °C, followed by HPLC separation of 2–3 mg of the products, we have isolated and characterised the following derivatives: C76F36, C76F38 (the main component, of C1 symmetry), C76F40 (five isomers, one of which has C2 symmetry), C76F42, C76F44, C76F40O, and C76F39OH (containing also some C76F37OH, and C76F41OH) and C78F42 (arising from traces of [78]fullerene present in the original [76]fullerene). Two unresolved mixtures were also obtained, one consisting of C76F32 and C78F38, the other consisting of other isomers of C76F36, C76F38, C76F40 and C76F42. The compounds are essentially colourless, but give lemon-coloured solutions in toluene due to formation of charge-transfer complexes.

References

  1. See e.g., O. V. Boltalina, A. Yu. Lukonin, A. A. Gorjunkov, V. K. Pavlovich, A. N. Rykov, V. A. Seniavin, L. N. Sidorov and R. Taylor, Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials, 1997, 4, 257 Search PubMed; O. V. Boltalina, A. Yu. Lukonin, V. K. Pavlovich, L. N. Sidorov, R. Taylor and A. K. Abdul-Sada, Fullerene Sci. Technol., 1998, 6, 469 Search PubMed; O. V. Boltalina, T. V. Avakian, V. Yu. Markov, I. D. Sorokin, L. N. Sidorov and R. Taylor, Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials, 1998, 6, 1152 CAS.
  2. O. V. Boltalina, V. Yu. Markov, R. Taylor and M. P. Waugh, Chem. Commun., 1996, 2549 RSC.
  3. A. G. Avent, O. V. Boltalina, P. W. Fowler, A. Yu. Lukonin, V. K. Pavlovich, J. P. B. Sandall, J. M. Street and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1998, 1319 RSC.
  4. O. V. Boltalina, A. Ya. Borschevskii, L. N. Sidorov, J. M. Street and R. Taylor, Chem. Commun., 1996, 529 RSC; O. V. Boltalina, J. M. Street and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1998, 649 RSC; O. V. Boltalina, M. Bühl, A. Khong, M. Saunders, J. M. Street and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1999, 1475 RSC.
  5. O. V. Boltalina, J. H. Holloway, E. G. Hope, J. M. Street and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1998, 1845 RSC.
  6. O. V. Boltalina, T. Drewello, A. Hirsch, V. Markov, U. Reuther and R. Taylor, Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials, 1999, 7, 462 Search PubMed.
  7. O. V. Boltalina, I. V. Gol'dt, T. Zatsepin, M. Spiridonov, S. I. Troyanov, L. N. Sidorov and R. Taylor, Molecular Nanostructures (Proc. XIth Int. Winterschool on Electronic Properties of Novel Materials), World Scientific, 1998, 114 Search PubMed; S. Kawasaki, T. Aketa, H. Touhara, F. Okino, O. V. Boltalina, I. V. Gol'dt, S. I. Troyanov and R. Taylor, J. Phys. Chem., 1999, 103, 1223 Search PubMed.
  8. R. Taylor, A. K. Abdul-Sada, O. V. Boltalina and J. M. Street, Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials, 1999, 7, 188 Search PubMed.
  9. A. G. Avent, P. R. Birkett, J. D. Crane, A. D. Darwish, G. J. Langley, H. W. Kroto, R. Taylor and D. R. M. Walton, J. Chem. Soc., Chem. Commun., 1994, 1463 RSC; P. R. Birkett, A. G. Avent, A. D. Darwish, H. W. Kroto, R. Taylor and D. R. M. Walton, J. Chem. Soc., Perkin Trans. 2, 1997, 457 RSC; P. R. Birkett, A. G. Avent, A. D. Darwish, I. Hahn, J. O'Loughlin, H. W. Kroto, G. J. Langley, R. Taylor and D. R. M. Walton, J. Chem. Soc., Perkin Trans. 2, 1997, 1121 RSC.
  10. P. R. Birkett, A. G. Avent, A. D. Darwish, H. W. Kroto, R. Taylor and D. R. M. Walton, Tetrahedron, 1996, 52, 5235 CrossRef.
  11. O. V. Boltalina, J. M. Street and R. Taylor, Chem. Commun., 1998, 1827 RSC.
  12. R. Taylor, Lecture Notes on Fullerene Chemistry; A Handbook for Chemists, Imperial College Press, London, 1999 Search PubMed.
  13. J. M. Hawkins and A. Meyer, Science, 1993, 260, 1918 CAS.
  14. A. D. Darwish, H. W. Kroto, R. Taylor and D. R. M. Walton, J. Chem. Soc., Perkin Trans. 2, 1996, 415 Search PubMed.
  15. P. R. Birkett, A. D. Darwish, H. W. Kroto, G. J. Langley, R. Taylor and D. R. M. Walton, J. Chem. Soc., Perkin Trans. 2, 1995, 511 RSC.
  16. A. Herrmann, F. Diederich, C. Thilgen, H.-U. ter. Meer and W. H. Müller, Helv. Chim. Acta, 1994, 77, 1689 CrossRef CAS; A. Herrmann and F. Diederich, Helv. Chim. Acta, 1996, 79, 1741 CrossRef CAS; J. Chem. Soc. Perkin Trans. 2, 1997, 1679 Search PubMed.
  17. C. Thilgen, A. Herrmann and F. Diederich, Angew. Chem., Int. Ed. Engl., 1997, 36, 2269 CrossRef CAS; C. Thilgen and F. Diederich, Top. Curr. Chem., 1999, 199, 135 CAS.
  18. O. V. Boltalina, A. K. Abdul-Sada, T. V. Avakyan, T. J. S. Dennis, V. Yu. Markov and R. Taylor, J. Phys. Chem. A, 1999, 103, 8189 CrossRef CAS.
  19. O. V. Boltalina, L. N. Sidorov, V. F. Bagryantsev, V. A. Seredenko, A. S. Zapolskii and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1996, 2275 RSC.
  20. B. W. Clare and D. L. Keppert, J. Mol. Struct. (THEOCHEM), 1994, 315, 71 CrossRef.
  21. R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1993, 813 RSC.
  22. R. Taylor, J. P. Hare, A. K. Abdul-Sada and H. W. Kroto, J. Chem. Soc., Chem. Commun., 1990, 1423 RSC.
  23. P. R. Birkett, A. G. Avent, A. D. Darwish, H. W. Kroto, R. Taylor and D. R. M. Walton, J. Chem. Soc., Chem. Commun., 1995, 683 RSC; S. J. Austin, P. W. Fowler, J. P. B. Sandall, P. R. Birkett, A. G. Avent, A. D. Darwish, H. W. Kroto, R. Taylor and D. R. M. Walton, J. Chem. Soc., Perkin Trans. 2, 1995, 1027 RSC; H. P. Spielman, G.-W. Wang, M. S. Meier and B. R. Weedon, J. Am. Chem. Soc., 1998, 120, 9865.
  24. Ref. 12, p. 44.
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