Reaction of silica-supported fullerene C60 with nonylamine vapor

The reaction of silica-supported [60]fullerene with vaporous nonylamine at 150 degreesC produces a mixture of addition products. Quantum chemical calculations, at the B3LYP/STO-3G level of theory, support that the addition reaction most likely takes place across the 6,6 bonds of C-60 pyracyclene units (and not across the 5,6 bonds). Numerous peaks were found in high-performance liquid chromatograms, apparently due to a large number of possible isomers. According to elemental analysis data (C:N ratio), the number of nonylamine molecules attached to C-60 is 3 on average. Thermogravimetric analysis of the nonylamine adduct showed two weight losses, one between 360 and 590 degreesC due to thermal decomposition of nonylamine moieties, and one between 725 and 840 degreesC due to decomposition of the remaining fullerene-derived carbonized material. Field-desorption mass spectrometric study revealed a number of molecular and fragment ions corresponding to the adducts with up to six nonylamine moieties attached to [60]fullerene; some of them were observed as multiply-charged ions. The temperature behavior of these peaks is similar to that for TGA, with maxima shifted to lower temperatures due to the cooperative effect of the strong electric field C-60 can be partially regenerated by pyrolysis of the nonylamine adduct, although at very low yields (below 1%, after heating at 350 degreesC under air for 2 h). (C) 2003 Elsevier Ltd. All rights reserved.