Effect of acid on the quantum yield of photodissociation of 9-(4-azidophenyl)acridine

The quantum yield of photodissociation of 9-(4-azidophenyl)acridine (1) is equal to 0.82, and that of its protonated form 2 is 6.9·10⁻³. The observed quantum yield of the system can smoothly be controlled in these limits varying the acidity of the medium. According to quantum chemical data, reactivity difference between neutral azide 1 and cation 2 is caused by the fact that in the lowest singlet-excited state (S₁) of azide 1 the antibonding σ*_NN molecular orbital is occupied, while this orbital remains unoccupied in the excited state of cation 2. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2655–2660, December, 2005.