Abstract
Abstract The photoinduced reaction of benzo[c]cinnoline (BCC) in strongly acidic aqueous alcohols, in which BCC exists in a monoprotonated form (BCCH+), was investigated. The initial step of the photoreaction was the hydrogen abstraction, which gave rise to 5,6-dihydroBCCH+, irrespective of the excitation wavelengths and the kind of alcohol (methanol, ethanol, or 2-propanol) used as a solvent. The subsequent reaction occurred upon irradiation by a light longer than 400 nm to afford 2,2′-diaminobiphenyl in ethanol, but not in methanol and 2-propanol. The 1-hydroxyethyl radical formed in the initial photoreduction appeared to participate in this reaction, donating its hydrogen atom to the ground-state 5,6-dihydroBCCH+. On the other hand, ultraviolet irradiation caused the subsequent photoreaction of 5,6-dihydroBCCH+, thus giving carbazole accompanied by the liberation of ammonia.
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