A Kinetic Study on the Chemiluminescence of 9-Alkylacridines upon Air Oxidation in Alkaline Aprotic Solvents

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Abstract
9-Methyl- (1a), 9-benzyl- (1b), 9-(diphenylmethyl)- (1c), and 9-ethylacridine (1d) were employed to obtain luminescent features of the acridines. The decay of chemiluminescence (CL) exhibits a pseudo-first order behavior with apparent rate constants 0.10, 3.30, 4.10, and 0.07 min−1 at 312 K for 1a, 1b, 1c, and 1d, respectively. A relatively high CL quantum yield (6.3×10−3) is provided for 1a, in contrast to low yields for 1b, 1c, and 1d (1.5×10−6, 1.1×10−5, and 1.3×10−4, respectively). A reaction mechanism involving a cleavage of a dioxetane intermediate to give excited singlet acridone anion is plausible for the luminescent reaction. In view of the fact that several dioxetanes decompose to give excited singlet products in high yields, the CL appears to arise from a minor reaction.
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