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The photobehaviour of four aza-analogues of EE-distyrylbenzene bearing the heteroatom inthe two side rings [1,4-di-(2-pyridylethenyl)benzene] or in the central ring [2,5-di-(phenylethenyl)pyridine,2,6-di(phenylethenyl)pyridine and the corresponding diene, 2,6-di(phenylbutadienyl)pyridine] has been investigatedin aqueous solutions at pH 2 and 9, where the molecules are in mono-protonated and neutralforms, respectively. The type of conjugation, linear for the first two compounds and crossed for the others,is particularly important in determining the spectral and photochemical properties. The main effects of theprotic solvent are a reduction of the radiative deactivation, prevalent in the corresponding hydrocarbons, andan increase of the reactive deactivation, very modest in the hydrocarbons. The increase in photoreactivity todetriment of fluorescence, observed in protic medium with respect to non-polar solvents, is drastically emphasizedin acid medium where the fluorescence quantum yield decreases by an order of magnitude leadingto high values of the EE→ZE photoisomerization quantum yield. The presence of conformational isomerism(two main conformers were detected) has been observed in both basic and acid media for compounds withcrossed conjugation and for the linearly conjugated 2,5 substituted pyridine. The results obtained give apicture of the different photobehaviour of the neutral and protonated species and indicate the experimentalconditions to favour a specific relaxation pathway

Protonation effect on the excited state behaviour of some aza‐analogues of EE‐distyrylbenzene