Research on Chemical Intermediates

, Volume 28, Issue 7–9, pp 817–830 | Cite as

Fullerenes (C60) versus heteroazafullerenes (C59N); a photophysical comparison of their monoadducts and hexaadducts

  • Dirk M. Guldi
  • Frank Hauke
  • Andreas Hirsch


The singlet and triplet excited state properties of a series of fullerene derivatives (C60) are compared to those of the corresponding heteroazafullerenes derivatives (C59N) by employing a variety of steady-state and time-resolved photophysical assays. The most far-reaching results infer that the C59N (2, 5) analogous of C60 (1, 4) are characterized by shorter singlet lifetimes (1.01/0.57 ns versus 1.80/1.75 ns) and weaker fluorescence quantum yields (1.6 × 10-4/2.1 × 10-4versus 6.0 × 10-4/1.09 × 10-3). This general conclusion applies for the monoadduct series (1, 2) and also for the highly functionalized hexaadducts (4, 5). Similarly, higher singlet energies (1.89 eV (4) versus 1.79 eV (1)) come together with higher fluorescence quantum yields for the hexaadducts than for the monoadducts.


Physical Chemistry Inorganic Chemistry Excited State Fullerene Quantum Yield 


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  1. 1.
    H. W. Kroto, J. R. Heath, S. C. O'Brien, R. F. Curl and R. E. Smalley, Nature 318, 162 (1985).Google Scholar
  2. 2. (a)
    E. Dietel, A. Hirsch, J. Zhou and A. Rieker, J. Chem. Soc. Perkin Trans. 2, 1357 (1998).Google Scholar
  3. 2. (b)
    X. Camps, E. Dietel, A. Hirsch, S. Pyo, L. Echegoyen, S. Hackbarth and B. Röder, Chem. Eur. J. 5, 2362 (1999).Google Scholar
  4. 2. (c)
    J.-F. Nierengarten, Chem. Eur. J. 6, 3667 (2000).Google Scholar
  5. 2. (d)
    M. Diekers, C. Luo, D. M. Guldi and A. Hirsch, Chem. Eur. J. 8 (2002).Google Scholar
  6. 3. (a)
    M. Prato and M. Maggini, Acc. Chem. Res. 31, 519 (1998).Google Scholar
  7. 3. (b)
    Fullerenes and Related Structures, A. Hirsch (Ed.), Top. Curr. Chem., Vol. 199. Springer, Berlin (1999).Google Scholar
  8. 3. (c)
    Lecture Notes on Fullerenes Chemistry, R. Taylor (Ed.). Imperial College Press, London (1999).Google Scholar
  9. 3. (d)
    F. Diederich and R. Kessinger, Acc. Chem. Res. 32, 537 (1999).Google Scholar
  10. 4. (a)
    H. Imahori and Y. Sakata, Adv. Mater. 9, 537 (1997).Google Scholar
  11. 4. (b)
    M. Prato, J. Mater. Chem. 7, 1097 (1997).Google Scholar
  12. 4. (c)
    N. Martin, L. Sanchez, B. Illescas and I. Perez, Chem. Rev. 98, 2527 (1998).Google Scholar
  13. 4. (d)
    H. Imahori and Y. Sakata, Eur. J. Org. Chem. 2445 (1999).Google Scholar
  14. 4. (e)
    D. M. Guldi, Chem. Commun. 321 (2000).Google Scholar
  15. 4. (f)
    D. M. Guldi and M. Prato, Acc. Chem. Res. 33, 695 (2000).Google Scholar
  16. 4. (g)
    C. A. Reed and R. D. Bolskar, Chem. Rev. 100, 1075 (2000).Google Scholar
  17. 4. (h)
    D. Gust, T. A. Moore and A. L. Moore, J. Photochem. & Photobiol. B 58, 63 (2000).Google Scholar
  18. 4. (i)
    D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res. 34, 40 (2001).Google Scholar
  19. 5.
    L. Echegoyen and L. E. Echegoyen, Acc. Chem. Res. 31, 593 (1998).Google Scholar
  20. 6. (a)
    H. Imahori, K. Hagiwara, T. Akiyama, M. Aoki, S. Taniguchi, T. Okada, M. Shirakawa and Y. Sakata, Chem. Phys. Lett. 263, 545 (1996).Google Scholar
  21. 6. (b)
    D. M. Guldi and K.-D. Asmus, J. Am. Chem. Soc. 119, 5744 (1997).Google Scholar
  22. 6. (c)
    H. Imahori, K. Tamaki, D. M. Guldi, C. Luo, M. Fujitsuka, O. Ito, Y. Sakata and S. Fukuzumi, J. Am. Chem. Soc. 123, 2607 (2001).Google Scholar
  23. 7. (a)
    J. C. Hummelen, B. Knight, J. Pavlovich, R. González and F. Wudl, Science 269, 1554 (1995).Google Scholar
  24. 7. (b)
    B. Nuber and A. Hirsch, Chem. Commun. 1421 (1996).Google Scholar
  25. 7. (c)
    M. Keshavarz-K, R. González, R. G. Hicks, G. Srdanov, V. I. Srdanov, T. G. Collins, J. C. Hummelen, C. Bellavia-Lund, J. Pavlovich, F. Wudl and K. Holczer, Nature 383, 147 (1996).Google Scholar
  26. 7. (d)
    C. Bellavia-Lund, R. González, J. C. Hummelen, R. G. Hicks, A. Sastre and F. Wudl, J. Am. Chem. Soc. 119, 2946 (1997).Google Scholar
  27. 7. (e)
    A. Gruss, K.-P. Dinse, A. Hirsch, B. Nuber and U. Reuther, J. Am. Chem. Soc. 119, 8728 (1997).Google Scholar
  28. 7. (f)
    C. Bellavia-Lund, M. Keshavarz-K, T. Collins and F. Wudl, J. Am. Chem. Soc. 119, 8101 (1997).Google Scholar
  29. 7. (g)
    B. Nuber and A. Hirsch, Chem. Commun. 405 (1998).Google Scholar
  30. 7. (h)
    J. C. Hummelen, C. Bellavia-Lund and F. Wudl, Top. Curr. Chem. 199, 93 (1999).Google Scholar
  31. 7. (i)
    B. Nuber and A. Hirsch, Acc. Chem. Res. 32, 795 (1999).Google Scholar
  32. 7. (k)
    F. Hauke and A. Hirsch, Chem. Commun. 2199 (1999).Google Scholar
  33. 7. (l)
    U. Reuther, A. Hirsch, Carbon 38, 1539 (2000).Google Scholar
  34. 7. (m)
    F. Hauke and A. Hirsch, Tetrahedron 57, 3697 (2001).Google Scholar
  35. 7. (n)
    N. Tagmatarchis, H. Shinohara, M. Fujitsuka and O. Ito, J. Org. Chem. 66, 8026 (2001).Google Scholar
  36. 8.
    S. L. Murov, I. Carmichael and G. L. Hug, Handbook of Photochemistry. Marcel Dekker, New York (1993).Google Scholar
  37. 9. (a)
    D. M. Guldi and K.-D. Asmus, J. Phys. Chem. A 101, 1472 (1997).Google Scholar
  38. 9. (b)
    J. E. Riggs and Y. P. Sun, J. Phys. Chem. A 103, 485 (1999).Google Scholar
  39. 9. (c)
    K. D. Ausman and W. B. Weisman, J. Am. Chem. Soc. 121, 1110 (1999).Google Scholar
  40. 9. (d)
    R. V. Bensasson, M. N. Berberan-Santos, M. Brettreich, J. Frederiksen, H. Gottinger, A. Hirsch, E. J. Land, S. Leach, D. J. McGarvey, H. Schonberger and C. Schroder, Phys. Chem. Chem. Phys. 3, 4679 (2001).Google Scholar
  41. 10.
    C. S. Foote, Top. Curr. Chem. 169, 347 (1994).Google Scholar
  42. 11.
    F. Hauke, A. Hirsch, S.-G. Liu, L. Echegoyen, A. Swartz, C. Luo and D. M. Guldi, Chem. Phys. Chem. 2, 195 (2002).Google Scholar
  43. 12.
    B. Ma, A. Weitz and F. Wudl, in: Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials, P. V. Kamat, D. M. Guldi and K. M. Kadish (Eds), p. 359. ECS, Pennington, NJ (1999).Google Scholar

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© VSP 2002 2002

Authors and Affiliations

  • Dirk M. Guldi
  • Frank Hauke
  • Andreas Hirsch

There are no affiliations available

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