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Science 15 September 1995:
Vol. 269. no. 5230, pp. 1554 - 1556
DOI: 10.1126/science.269.5230.1554
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Articles

Isolation of the Heterofullerene C59N as Its Dimer (C59N)2

Jan C. Hummelen 1, Brian Knight 1, James Pavlovich 1, Rosario González 1, and Fred Wudl 1

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

The heterofullerene ion C59N+ is formed efficiently in the gas phase during fast atom bombardment mass spectroscopy of a cluster-opened N-MEM (N-methoxyethoxy methyl) ketolactam. This transformation is shown to occur also in solution in the presence of strong acid, affording biazafullerenyl (C59N)2 in good yield. It is proposed that the azafullerene dimer is formed upon in situ reduction of the highly reactive azafulleronium ion. The isolation and characterization of biazafullerenyl opens a viable route for the preparation of other heterofullerenes in solution.

Submitted on July 5, 1995
Accepted on August 11, 1995

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Science. ISSN 0036-8075 (print), 1095-9203 (online)