ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Rational Design of Azothiophenes-Substitution Effects on the Switching Properties.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed.
- Coupling Photochromism and Charge Transport in π-Extended Arylazo Oligothiophenes and Oligothienoacenes.Journal of the American Chemical Society · 2026Article
- Mechanistic insights into azo compound back-isomerization from spin-flip time-dependent DFT combined with Marcus theory.Chemical science · 2026Article
- The Nonadiabatic Nature of the Substituent Effects in Azobenzene.Angewandte Chemie (International ed. in English) · 2026Article
- Mechanistic Insight into Para-Substituent Control of Thermal Half-Lives in Arylazopyrazole Photoswitches.Angewandte Chemie (International ed. in English) · 2025Article
- Alternating Orthogonal Switching in a Thiophenyl-Phenyl-Bis-Azobenzene Switch.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Triplet Spin Delocalization and Temperature Dependence for Adiabatic and Non-AdiabaticJournal of the American Chemical Society · 2025Article
- Recent Developments in the Optical Control of Adrenergic Signaling.Medicinal research reviews · 2025Review
- Semi-automated screening of azobezenes for solar energy storage using extended tight binding methods.Scientific reports · 2025Article
- Conceptual expansion of photomedicine for spatiotemporal treatment methods.RSC medicinal chemistry · 2025Review
- Predictive modeling of visible-light azo-photoswitches' properties using structural features.Journal of cheminformatics · 2025Article
- Switching Sides: Regiochemistry and Functionalization Dictate the Photoswitching Properties of Imines.Angewandte Chemie (International ed. in English) · 2025Article
- Structural and Electronic Properties of Novel Azothiophene Dyes: A Multilevel Study Incorporating Explicit Solvation Effects.Molecules (Basel, Switzerland) · 2024Article
- Detour to success: photoswitchingChemical science · 2024Review
- The effect of substituent position and solvent on thermal Z‒E isomerization of dihydroquinolylazotetrazole dyes: kinetic, thermodynamic, and spectral approaches.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2024Article
- Singlet and Triplet Pathways Determine the ThermalThe journal of physical chemistry letters · 2023Article
- Thermal Half-Lives of Azobenzene Derivatives: Virtual Screening Based on Intersystem Crossing Using a Machine Learning Potential.ACS central science · 2023Article
- Electrocatalytic Energy Release of Norbornadiene-Based Molecular Solar Thermal Systems: Tuning the Electrochemical Stability by Molecular Design.ChemSusChem · 2022Article
- Electrochemically Triggered Energy Release from an Azothiophene-Based Molecular Solar Thermal System.ChemSusChem · 2022Article
- Molecular photoswitches in aqueous environments.Chemical Society reviews · 2021Review
- Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches.Journal of the American Chemical Society · 2021Article
Corrections and comments
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Authors and funding
2 authors.
Funding
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-π 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.
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