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

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UDC.coleccionInvestigación
UDC.departamentoQuímica
UDC.endPage6565
UDC.grupoInvQuímica Molecular e de Materiais (QUIMOLMAT)
UDC.institutoCentroCICA - Centro Interdisciplinar de Química e Bioloxía
UDC.issue19
UDC.journalTitleThe Journal of Organic Chemistry
UDC.startPage6559
UDC.volume91
dc.contributor.authorVila, Alejandro
dc.contributor.authorBlandón-Cumbreras, Francisco G.
dc.contributor.authorPauls, Mike
dc.contributor.authorDíaz-Abellás, Mauro
dc.contributor.authorBlanco-Gómez, Arturo
dc.contributor.authorPeinador, Carlos
dc.contributor.authorRemón, Patricia
dc.contributor.authorBannwarth, Christoph
dc.contributor.authorPischel, Uwe
dc.contributor.authorGarcía, Marcos D.
dc.date.accessioned2026-07-24T10:29:22Z
dc.date.available2026-07-24T10:29:22Z
dc.date.issued2026-05-04
dc.description.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.
dc.description.sponsorshipThe authors are grateful for the funding received from the MCIN/AEI/10.13039/501100011033 and ERDF A way of making Europe (PID2022-137361NB-I00 for C.P./M.D.G., PID2020-119992GB-I00 and PID2023-152556NB-I00 for U.P. and predoctoral contract PRE2023-001520 for F.G.B.-C.), and the Consellería de Cultura, Educación e Universidade da Xunta de Galicia (ED431C 2022/39). M.D.-A. thanks Ministerio de Universidades for his predoctoral fellowship (FPU21/06302). A.B.-G. thanks the Consellería de Cultura, Educación e Universidade da Xunta de Galicia for his postdoctoral fellowship (ED481D-2024-020). M.D.G. thanks CESGA (Xunta de Galicia) for computational time. C.B. acknowledges funding from the Federal Ministry of Education and Research (BMBF) and the Ministry of Culture and Science of the German State of North Rhine-Westphalia (MKW) under the Excellence Strategy of the Federal Government and the Länder (RWTH JPI Fellowship), as well as funding from the MKW via the NRW Rückkehrprogramm
dc.description.sponsorshipXunta de Galicia; ED431C 2022/39
dc.description.sponsorshipXunta de Galicia; ED481D-2024-020
dc.identifier.citationVila, 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.
dc.identifier.doi10.1021/acs.joc.5c02962
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.urihttps://hdl.handle.net/2183/48932
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-137361NB-I00/ES/NUEVOS INTERRUPTORES MOLECULARES DE BIPIRIDINIO. HACIA LA FUNCIONALIDAD QUIMICA CONTROLADA EN MEDIO ACUOSO
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-119992GB-I00/ES/FOTOINTERRUPTORES DIARILETENO EN EL ENFOQUE DE APLICACIONES FOTONICAS Y SUPRAMOLECULARES AVANZADAS
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2023-152556NB-I00/ES/EXPANSION DE LA PLATAFORMA BASHY (SALICILIDENHIDRAZONAS DERIVADAS DE ACIDOS BORONICOS) Y COMPUESTOS DERIVADOS: EXPLOTACION INNOVADORA DE FACTORES ELECTRONICOS Y ESTRUCTURALES
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PREP2023-001520/ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/MUNI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/FPU21%2F06302/ES
dc.relation.urihttps://doi.org/10.1021/acs.joc.5c02962
dc.rightsAttribution 4.0 Internationalen
dc.rights.accessRightsopen access
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.titlePhotovermellogens: Minimalistic Pyridinium-Based Acylhydrazones with Photoswitchable Basicity for Operation in Aqueous Media
dc.typejournal article
dc.type.hasVersionVoR
dspace.entity.typePublication
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relation.isAuthorOfPublication86a2d4e7-c65e-4cbb-ad78-02434b0eca6d
relation.isAuthorOfPublication.latestForDiscovery2249e790-a38a-46e4-9526-0ff46d9b9531

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