The heterofullerene ion C(59)N(+) 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 (C(59)N)(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.

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Two phosphonium cation-based ionic liquids (ILs) were studied as additive to a mineral oil. Solubility tests and TGA of neat samples were performed. Three concentrations of the ILs were used in the tribological tests. Base oil-ZDDP mixtures were used as comparison samples. Tribological tests were made using a reciprocating ball-on-disc configuration. Load ramp and Stribeck curve tests were also performed. The worn surface was studied by different techniques. The results showed similar and better friction reduction properties for ILs-or ZDDP-containing mixtures than the neat base oil. The [P 66614 ][(iC8) 2 PO 2 ] -containing mixtures outperformed the antiwear behavior of the other samples. XPS results showed different mechanisms of lubrication when using ILs or ZDDP.

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