Bowl-shaped PAH has C60-like reactivity

Abstract

A bowl-shaped polycyclic aromatic hydrocarbon (PAH), C 26 H 12 , exhibits reactivity that is similar to that of soccer-ball-shaped buckminsterfullerene, C 60 , according to chemists at Boston College. The result suggests that the reactivity of fullerenes—which is driven largely by the strain associated with curving an aromatic network—can be extended to curved but not closed molecules. Hindy E. Bronstein, a Boston College graduate student, described the research on the bowl-shaped fullerene fragment to a symposium in Cancun. Bronstein carried out the work with Boston College chemistry professor Lawrence T. Scott. Bronstein and Scott find that the C 26 H 12 PAH they synthesize by flash pyrolysis of a suitable precursor undergoes reactions at interior carbon atoms—that is, trigonal carbon atoms shared by three rings. By contrast, the chemistry of PAHs, most of which are flat molecules, overwhelmingly occurs at carbons located around the edges of the molecules, Scott points out. This bridges the chasm bet...