Substituent effects in <i>N</i> -acetylated phenylazopyrazole photoswitches

Phenylazopyrazole photoswitches proved to be valuable structural motifs for various applications ranging from materials science to medicine. Despite their potential, their structural diversity is still limited and a larger pool of substitution patterns remains to be systematically investigated. This is paramount as electronic effects play a crucial role in the behavior of photoswitches and a deeper understanding enables their straightforward development for specific applications. In this work, we synthesized novel <i>N</i>-acylpyrazole-based photoswitches and conducted a comparative study with 33 phenylazopyrazoles, comparing their photoswitching properties and the impact of electronic effects. Using UV-vis and NMR spectroscopy, we discovered that simple acylation of the pyrazole moiety leads to increased quantum yields of isomerization, long <i>Z</i>-isomer life-times, good spectral separation, and high photostability.