ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
The Photoisomerization Pathway(s) of Push-Pull Phenylazoheteroarenes*.
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 5 papers.
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Who cites it
5 citing papers in PubMed, 11 citations in OpenAlex.
- Photoswitches beyond azobenzene: a beginner's guide.Beilstein journal of organic chemistry · 2025Review
- From Organic Fragments to Photoswitchable Catalysts: The OFF-ON Structural Repository for Transferable Kernel-Based Potentials.Journal of chemical information and modeling · 2024Article
- SPAJournal of chemical theory and computation · 2024Article
- Tuning the Thermal Stability and Photoisomerization of Azoheteroarenes through Macrocycle Strain*.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- The Photoisomerization Pathway(s) of Push-Pull Phenylazoheteroarenes*.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Azoheteroarenes are the most recent derivatives targeted to further improve the properties of azo-based photoswitches. Their light-induced mechanism for trans-cis isomerization is assumed to be very similar to that of the parent azobenzene. As such, they inherited the controversy about the dominant isomerization pathway (rotation vs. inversion) depending on the excited state (nπ* vs. ππ*). Although the controversy seems settled in azobenzene, the extent to which the same conclusions apply to the more structurally diverse family of azoheteroarenes is unclear. Here, by means of non-adiabatic molecular dynamics, the photoisomerization mechanism of three prototypical phenyl-azoheteroarenes with increasing push-pull character is unraveled. The evolution of the rotational and inversion conical intersection energies, the preferred pathway, and the associated kinetics upon both nπ* and ππ* excitations can be linked directly with the push-pull substitution effects. Overall, the working conditions of this family of azo-dyes is clarified and a possibility to exploit push-pull substituents to tune their photoisomerization mechanism is identified, with potential impact on their quantum yield.
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Registered trials
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