ArticleAngewandte Chemie (International ed. in English)2026
Overcrowded Alkene Photo-Redox-Switches Based on Quinolinium/Carbene Building Blocks.
Article in Angewandte Chemie (International ed. in English), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The design and characterization of a novel class of overcrowded alkene-based photo/redox switches are presented. Folded and twisted tetrasubstituted alkenes are prepared in a modular fashion by the combination of quinolinium salts and stable carbenes. The compounds show multi-stimuli responsive properties: besides electrochemical redox-switching, which allows C─C bond rotation via a two-electron redox process, non-symmetrical compounds enable photochemically driven E/Z-switching. The different oxidation states can be isolated and fully characterized including structural changes verified by x-ray diffraction. Excellent photostability for E/Z-switching was observed in selected cases and is supported by UV-vis, NMR, and x-ray data as well as computations. TD-DFT calculations accurately predict the absorption properties of the E/Z-photo-switches and the substituent effects governing photo-stationary states and half-lifes. While the thermal E/Z-back-switching proceeds via a rather high energy barrier featuring a diradical transition state, electrochemical switching via the radical cation oxidation state allows instantaneous E/Z-isomerization, which is catalytic in electrons (electron hole catalysis). The mechanism of the switching process is supported in detail by quantum chemical calculations including nonadiabatic molecular dynamics simulations.
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