Year: 2025
Type: article
Abstract: Phenyl azopyrazole 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 N-acyl pyrazole-based photoswitches and conducted a comparative study with 33 phenyl azopyrazoles, 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 Z–isomer lifetimes, good spectral separation, and high photostability.
DOI: 10.3762/bjoc.21.66
Institutions: University of Göttingen, Uppsala University, Multiscale Bioimaging
Language: English
Subfield: Materials Chemistry
Field: Materials Science
Domain: Physical Sciences
Open Access status: diamond
Awards: Synthesis and development of novel photoactuators and photoreactions by computer-aided design, Chromatically Orthogonal Building Blocks for the Next-Generation Opto-Chemical Tools and Photopharmaceuticals, G2747900335, G2749558419, G3445732291, GRK 2455: BEnch Bewertende Experimente für die numerische Quantenchemie, G584537252, EXC 2067: Multiscale Bioimaging: Von molekularen Maschinen zu Netzwerken erregbarer Zellen, G7987891391
OpenAlex ID: W4409817077