Journal article

Authors list: Heindl, AH; Wegner, HA

Publication year: 2020

Pages: 13730-13737

Journal: Chemistry - A European Journal

Volume number: 26

Issue number: 60

ISSN: 0947-6539

eISSN: 1521-3765

Open access status: Hybrid

DOI Link: https://doi.org/10.1002/chem.202001148

Publisher: Wiley

Abstract: 
A series of substituted azothiophenes was prepared and investigated toward their isomerization behavior. Compared to azobenzene (AB), the presented compounds showed red-shifted absorption and almost quantitative photoisomerization to their (Z) states. Furthermore, it was found that electron-withdrawing substitution on the phenyl moiety increases, while electron-donating substitution decreases the thermal half-lives of the (Z)-isomers due to higher or lower stabilization by a lone pair-pi interaction. Additionally, computational analysis of the isomerization revealed that a pure singlet state transition state is unlikely in azothiophenes. A pathway via intersystem crossing to a triplet energy surface of lower energy than the singlet surface provided a better fit with experimental data of the (Z)->(E) isomerization. The insights gained in this study provide the necessary guidelines to design effective thiophenylazo-photoswitches for applications in photopharmacology, material sciences, or solar energy harvesting applications.

Harvard Citation style: Heindl, A. and Wegner, H. (2020) Rational Design of Azothiophenes—Substitution Effects on the Switching Properties, Chemistry - A European Journal, 26(60), pp. 13730-13737. https://doi.org/10.1002/chem.202001148

APA Citation style: Heindl, A., & Wegner, H. (2020). Rational Design of Azothiophenes—Substitution Effects on the Switching Properties. Chemistry - A European Journal. 26(60), 13730-13737. https://doi.org/10.1002/chem.202001148