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Substituents impact on the mechanism of photochemical E-Z isomerization of diarylethene triazoles

Stilbene derivatives have been in the focus of scientific interest over the years as model compounds in the fundamental investigation of their E-Z photoisomerization reaction [1]. In this work, photochemical reactivity in the Z-E isomerization for two heterostilbenes containing 1, 2, 3-triazole unit were investigated theoretically and experimentally by irradiation experiments, fluorescence and laser flash photolysis (LFP) [2]. Fluorescence measurements for ortho-methyl derivative 1 indicated that the Z → E isomerization takes place in an adiabatic reaction on the potential energy surface of the S1 state. On the contrary, the para-nitro derivative 2 undergoes the Z → E isomerization via a triplet excited state, which was detected by LFP. All experimental observations were corroborated by computations. The mechanistic investigation presented gives insight in the fundamental and simple Z → E isomerization and provides new findings which are important in the rational design of different photoreactive diarylethene derivatives used in different fields of science.

E-Z isomerization, diarylethenes, triazoles, quantum-chemical calculations, LFP, heterostilbenes

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