Photoinduced cleavage of the carbon-carbon bond of 9-(1-naphthylmethyl)-10-methyl-9,10-dihydroacridines by perchloric acid via intramolecular electron-transfer excitation

Abstract

The C(9)-C bond of 9-(1-naphthylmethyl)-10-methyl-9,10-dihydroacridine (AcrHR) is readily cleaved by HClO 4 , in acetonitrile (MeCN) under irradiation of the absorption band of AcrHR to yield RH and AcrH + . The dependence of the fluorescence maximum on solvent dielectric constant indicates a highly polar singlet excited state with the dipole moment of ca. 15.6 D, while the fluorescence maximum of 9,10-dihydro-10-methylacridine (AcrH 2 ) is insensitive to the solvent