The unexpected and important role of alcohol stabilizer in thermal cis-trans isomerization of push-pull dyes in chloroform solution

The study demonstrates the influence of ethanol as a stabilizer in chloroform on the thermal cis-trans isomerization kinetics of photochromic compounds based on azobenzene and azopyridine derivatives. The significance of the addition of ethanol as a stabilizer in chloroform-based solutions on the isomerization reaction of the hydroxy- and the 6-hydroxylalkoxy-substituted azo compounds was investigated. The results have revealed that the presence of a polar stabilizer in a solvent can significantly reduce the reaction rate constant of the dark cis-trans isomerization due to the formation of hydrogen bonds at both ends of the azo-chromophore, thereby inhibiting the isomerization. Furthermore, a stabilizer can facilitate the reversion of azo-hydrazone tautomers of azophenols to their azobenzene form, resulting in a decrease in the reaction rate constant. The research presented in this paper can be essential for scientists who study the kinetics of the trans-cis and the cis-trans isomerization reactions of azo-chromophores. The results show that the use of solvents with polar stabilizers should be rather avoided, as their usage without information about stabilizers can lead to different experimental data. The authors should ensure that detailed information about stabilizers used in unstable solvents is included in the experimental section of their works (a detail currently often omitted in the literature). © 2024 Elsevier Ltd