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Photovermellogens: Minimalistic Pyridinium-Based Acylhydrazones with Photoswitchable Basicity for Operation in Aqueous Media

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URI: https://hdl.handle.net/2183/48932
DOI: 10.1021/acs.joc.5c02962

Publication date

2026-05-04

Authors

Vila, Alejandro
Blandón-Cumbreras, Francisco G.
Pauls, Mike
Remón, Patricia
Bannwarth, Christoph
Pischel, Uwe

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Vila, A.; Blandón-Cumbreras, F. G.; Pauls, M.; Díaz-Abellás, M.; Blanco-Gómez, A.; Peinador, C.; Remón, P.; Bannwarth, C.; Pischel, U.; García, M. D. Photovermellogens: Minimalistic Pyridinium-Based Acylhydrazones with Photoswitchable Basicity for Operation in Aqueous Media. J. Org. Chem. 2026, 91 (19), 6559–6565. https://doi.org/10.1021/acs.joc.5c02962.

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Abstract

[Abstract] Examples of a new class of synthetically straightforward and hydrolytically inert photoswitchable acylhydrazones, named photovermellogens, have been successfully developed and comprehensively studied using state-of-the-art spectroscopic and computational techniques. These compounds present photoswitchable basicity, with irradiation promoting E→Z photoisomerizations, which result in the generation of a less acidic species. The observed ΔpKa values > 1.5 within the biologically relevant window underscore the potential of photovermellogens as versatile platforms for light-triggered pH control.

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https://doi.org/10.1021/acs.joc.5c02962

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