THE electronic and geometric properties of C60 can be perturbed by replacing one or more carbon atoms of the fullerene skeleton with an atom of a different element. Exchange of one carbon atom with nitrogen, a trivalent atom with a lone pair of electrons, produces the azafullerene radical C59N, which is isoelectronic with the C60 radical anion. The process is slightly similar to doping silicon with phosphorus1. We have previously described the synthesis of the azafullerene dimer2; here we report the bulk preparation of the simplest azafullerene, C59HN. The electronic, vibrational and 13C NMR spectroscopic features of C59HN are similar to those of the dimer2, except for the signature of the sp3 (C–H) carbon. C59HN should open the door to a new chemistry of heterofullerenes.

Access optionsAccess options

Rent or Buy article

Get time limited or full article access on ReadCube.


All prices are NET prices.


  1. 1

    Guo, T., Jin, C. & Smalley, R. E. J. Phys. Chem. 95, 4948–4950 (1991).

  2. 2

    Hummelen, J. C., Knight, B., Pavlovich, J., González, R. & Wudl, F. Science 269, 1554–1556 (1995).

  3. 3

    Keshavarz-K, M., Knight, B., Srdanov, G. & Wudl, F. J. Am. Chem. Soc. 117, 11371–11372 (1995).

  4. 4

    Kitagawa, T., Tanaka, T., Takata, Y., Takeuchi, K. & Komatsu, K. J. Org. Chem. 60, 1490–1491 (1995).

  5. 5

    Prassides, K. et al. Science 271, 1833–1835 (1996).

  6. 6

    Andreoni, W., Curioni, A., Keshavarz-K, M. & Wudl, F. J. Am. Chem. Soc. (in the press).

  7. 7

    Niyazymbetov, M. E., Evans, D. H., Lerke, S. A., Cahill, P. A. & Henderson, C. C. J. Phys. Chem. 98, 13093–13098 (1994).

  8. 8

    Guarr, T. F., Meier, M. S., Vance, V. K. & Clayton, M. J. Am. Chem. Soc. 115, 9862–9863 (1993).

  9. 9

    Boyd, P. D. W. et al. J. Am. Chem. Soc. 117, 2907–2914 (1995).

  10. 10

    Dubois, D. & Kadish, K. J. Am. Chem. Soc. 113, 7773–7774 (1991).

  11. 11

    Xie, Q., Anois, F. & Echegoyer, L. J. Am. Chem. Soc. 115, 9818–9819 (1993).

Download references

Author information


  1. Departments of Chemistry and Materials, Institute for Polymers and Organic Solids, University of California, Santa Barbara, California, 93106–5090, USA

    • Majid Keshavarz-K
    • , Rosario González
    • , Robin G. Hicks
    • , Gordana Srdanov
    • , Vojislav I. Srdanov
    • , Tasha G. Collins
    • , Jan Cornelis Hummelen
    • , Cheryl Bellavia-Lund
    • , James Pavlovich
    •  & Fred Wudl
  2. Department of Physics, University of California, Los Angeles, California, 90024, USA

    • Karoly Holczer


  1. Search for Majid Keshavarz-K in:

  2. Search for Rosario González in:

  3. Search for Robin G. Hicks in:

  4. Search for Gordana Srdanov in:

  5. Search for Vojislav I. Srdanov in:

  6. Search for Tasha G. Collins in:

  7. Search for Jan Cornelis Hummelen in:

  8. Search for Cheryl Bellavia-Lund in:

  9. Search for James Pavlovich in:

  10. Search for Fred Wudl in:

  11. Search for Karoly Holczer in:

About this article

Publication history



Issue Date


Further reading


By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.