Letter | Published:

Synthesis of hydroazafullerene C59HN, the parent hydroheterofullerene

Nature volume 383, pages 147150 (12 September 1996) | Download Citation

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Abstract

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.

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Affiliations

  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

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https://doi.org/10.1038/383147a0

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