Substituent Effects in Acetylated Phenyl Azopyrazole Photoswitches

Submitting author affiliation:
Universität Göttingen, Göttingen, Germany

Beilstein Arch. 2025, 20257. https://doi.org/10.3762/bxiv.2025.7.v1

Published 10 Feb 2025

Preprint
cc-by Logo

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.

Keywords: photoswitches; photochromism; azobenzenes; substituent effects; azopyrazoles;

Supporting Information

Format: PDF Size: 13.2 MB   Download

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Tovtik, R.; Marzin, D.; Weigel, P.; Crespi, S.; Simeth, N. A. Beilstein Arch. 2025, 20257. doi:10.3762/bxiv.2025.7.v1

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

OTHER BEILSTEIN-INSTITUT OPEN SCIENCE ACTIVITIES