Formation of C 70Ph 10 and C 70Ph 8 from the electrophile C 70Cl 10

Abstract

In the presence of ferric chloride, benzene readily undergoes electrophilic substitution by C 70Cl 10 to give both yellow C 70Ph 10 and orange-red C 70Ph 8, each of which is luminescent. Their structures have been characterised by 1H and 13C NMR spectroscopy [including nOe and two-dimensional (COSY) analysis], and by UV, IR, and mass spectrometry. C 70Ph 10 is not formed directly from C 70Cl 10, but rather by further phenylation of the intermediate C 70Ph 8. The adjacent phenyl groups of C 70Ph 10 are sterically prevented from rotating at room temperature.