ArticleAngewandte Chemie (International ed. in English)2020
Thiophenylazobenzene: An Alternative Photoisomerization Controlled by Lone-Pair⋅⋅⋅π Interaction.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Coupling Photochromism and Charge Transport in π-Extended Arylazo Oligothiophenes and Oligothienoacenes.Journal of the American Chemical Society · 2026Article
- 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
- Semi-automated screening of azobezenes for solar energy storage using extended tight binding methods.Scientific reports · 2025Article
- Aryl Azocyclopropeniums: Minimalist, Visible-Light Photoswitches.Journal of the American Chemical Society · 2024Article
- Arylazobenzimidazoles: versatile visible-light photoswitches with tuneableChemical science · 2024Article
- Electrochemically Triggered Energy Release from an Azothiophene-Based Molecular Solar Thermal System.ChemSusChem · 2022Article
- Solvent dielectric delimited nitro-nitrito photorearrangement in a perylenediimide derivative.Chemical science · 2022Article
- Molecular photoswitches in aqueous environments.Chemical Society reviews · 2021Review
- Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches.Journal of the American Chemical Society · 2021Article
- Rational Design of Azothiophenes-Substitution Effects on the Switching Properties.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Thiophenylazobenzene: An Alternative Photoisomerization Controlled by Lone-Pair⋅⋅⋅π Interaction.Angewandte Chemie (International ed. in English) · 2020Article
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6 authors.
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Abstract
Azoheteroarene photoswitches have attracted attention due to their unique properties. We present the stationary photochromism and ultrafast photoisomerization mechanism of thiophenylazobenzene (TphAB). It demonstrates impressive fatigue resistance and photoisomerization efficiency, and shows favorably separated (E)- and (Z)-isomer absorption bands, allowing for highly selective photoconversion. The (Z)-isomer of TphAB adopts an unusual orthogonal geometry where the thiophenyl group is perfectly perpendicular to the phenyl group. This geometry is stabilized by a rare lone-pair⋅⋅⋅π interaction between the S atom and the phenyl group. The photoisomerization of TphAB occurs on the sub-ps to ps timescale and is governed by this interaction. Therefore, the adoption and disruption of the orthogonal geometry requires significant movement along the inversion reaction coordinates (CNN and NNC angles). Our results establish TphAB as an excellent photoswitch with versatile properties that expand the application possibilities of AB derivatives.
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