Studies on chemiluminescent compounds. I. Syntheses of acylsubstituted anthracene derivatives and their chemiluminescence.

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New anthracene derivatives with a –COCH– group, such as 1,5-dipropionylanthracene, 1,8-dipropionylanthracene, 1,5-di-isobutyrylanthracene, 1,8-diisobutyrylanthracene, 1,5-bis[3-(methoxycarbonyl)propionyl]anthracene, 1,8-bis[3-(methoxycarbonyl)propionyl] anthracene, 1,5-bis(cyclohexylcarbonyl) anthracene, 3,7-diisopropyl-1,5-diisobutyrylanthracene, and 5-dimethylamino-4-isobutyryl-1-methoxyanthracene (<B>10</B>) have been synthesized. Their direct chemiluminescences were studied by air oxidation in alkaline solutions. The properties of the chemiluminescence have been found to be influenced by not only the class of the C–H bond adjacent to the carbonyl group but also by the electronic properties of the aromatic ring system, the solvent, and the additive. <B>10</B> exhibited the longest chemiluminescence. This chemiluminescent phenomenon might be explained by a chemically initiated electron exchange luminescence (CIEEL) mechanism.
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