Photoinduced excited state proton rearrangement of 6-hydroxyquinoline along a hydrogen-bonded acetic acid wire

6-Hydroxyquinoline (6-HQ) in benzene emits normal fluorescence around 357 nm. In the presence of acetic acid (HOAc), it exhibits two more bands at ∼419 nm and a large Stokes shifted one at ∼583 nm with decreased intensity of the normal fluorescence. It appears to form (1:1) and (1:2) complexes-(1:2) 6-HQ/HOAc undergoes an excited state proton rearrangement (via HOAc wire) resulting in keto tautomer (emitting at ∼583 nm). This appears to be in line with recent findings where ammonia wires facilitate proton/hydrogen translocation (Science, 302, 1736, 2003). However, (1:1) 6-HQ/HOAc exhibits intermediate emission (∼419 nm) presumably due to ESIPT.