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

Science  15 Sep 1995:
Vol. 269, Issue 5230, pp. 1554-1556
DOI: 10.1126/science.269.5230.1554


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.