Synthesis and photochemistry of novel 1,2,3-triazole di-heterostilbenes. An experimental and computational study

Abstract

The synthesis, photoreactivity, and spectroscopic characterization of novel 1,2,3-triazole di-heterostilbenes bearing various aliphatic and aromatic substituents on the triazole rings were thoroughly explored. By introducing triazole rings into the o-divinylbenzene moiety, compared with the 2-furyl and 2-thienyl heteroanalogues, these compounds did not show any photochemical reactivity toward intramolecular cycloaddition reactions or electrocyclization processes. The research is further extended to the more in-depth examination of photochemical and photophysical characteristics of the investigated triazolo-stilbenes to explain the lack of reactivity in intramolecular photochemical cyclizations by configuration and substituent effects. Conformations of synthetically obtained novel triazoles are examined by Density Functional Theory (DFT). The time dependent-DFT approach was employed to obtain additional insight into the properties observed with UV/Vis spectroscopy. The frontier orbital energy was computationally investigated to determine the influence of cis–trans isomerism and the nature of substituents on the spectroscopic properties of the triazoles. Along with our previous studies of similar compounds containing furan and thiophene, respectively, this study shows that introducing various heteroaromatic rings induces diverse photochemistry and photophysics due to the conformational changes and change in electronic distribution within the molecular system.