Near-Complete Bidirectional Photoisomerization of para-Dialkylamino-Substituted Arylazopyrazoles under Violet and Green or Red Lights

para-Dimethylamine- and para-pyrrolidine-substituted arylazopyrazoles display very high to near-quantitative or quantitative bidirectional isomerization under violet and green or red lights in both polar (DMSO and DMSO/aqueous buffer, pH 7.5) and nonpolar solvents. These switches confer a reasonable thermal stability to their cis-states (t(1/2) approximate to 4-7 h in DMSO and DMSO/buffer) and also show a high level of resistance to photobleaching and an impressive stability to reduction by glutathione. Using DFT calculations, attempts have been made to decipher the photophysical properties and thermal stabilities of the cis isomers.

Automated summary

This study discovered that arylazopyrazoles with para-dimethylamine and para-pyrrolidine substitutions display very high or near-quantitative bidirectional isomerization under different light sources, and exhibit reasonable thermal stability and impressive stability to reduction.