Synthesis, spectral properties and photobehaviour of push–pull distyrylbenzene nitro-derivatives

Six novel asymmetric 2,5-distyryl-furan, 2,5-distyryl-thiophene and 2,6-distyrylpyridine derivatives, bearing an electron acceptor (p-nitro) group at one side and an electron donor (p-methoxy or p-dimethylamino) group at the other side, have been prepared. The experimental absorption properties have been measured and compared with the computed parameters. Theoretical and experimental results indicate that one conformational isomer (the compressed one) is largely prevalent in all compounds. The measured radiative and reactive relaxation properties of these donor/acceptor disubstituted compounds were also compared with those of the unsubstituted analogues previously investigated. The presence of the donor/acceptor groups leads to a significant increase of the charge transfer character of both the ground and the excited states and to strong red shifts of the absorption spectra, an effect that can be useful for potential applications in material science. The fluorescence/photoisomerization competition of the furan and thiophene derivatives was found to be rather similar to that of the unsubstituted analogues whereas significant changes were found for the pyridine derivatives where a drastic decrease of fluorescence, a sizable increase of photoisomerization and a predominance of radiationless deactivation to the ground state becomes operative.

► Six new push–pull distyrylbenzene analogues have been synthesized.
► Spectral and relaxation properties have been measured.
► The effect of furan, thiophene or pyridine central groups has been investigated.
► Pyridine derivatives have the main effect on the emission/reaction competition.