Getting a molecular grip on the half-lives of iminothioindoxyl photoswitches

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dc.contributor.authorBoëtius, Melody E.
dc.contributor.authorHoorens, Mark W. H.
dc.contributor.authorOšťadnický, Martin
dc.contributor.authorLaurent, Adéle D.
dc.contributor.authorDi Donato, Mariangela
dc.contributor.authorVan Wingaarden, Aldo C. A.
dc.contributor.authorHilbers, Michiel
dc.contributor.authorFeringa, Ben L.
dc.contributor.authorBuma Wybren, Jan
dc.contributor.authorMedveď, Miroslav
dc.contributor.authorSzymanski, Wiktor
dc.date.accessioned2025-11-26T11:00:34Z
dc.date.available2025-11-26T11:00:34Z
dc.date.issued2024
dc.descriptionIn: Chemical Science. Cambridge : Royal Society of Chemistry, 2024. ISSN 2041-6520. Vol. 15, no. 35 (2024), pp. 14379-14389.
dc.description.abstractVisible-light-operated photoswitches are of growing interest in reversibly controlling molecular processes, enabling for example the precise spatiotemporal focusing of drug activity and manipulating the properties of materials. Therefore, many research efforts have been spent on seeking control over the (photo)physical properties of photoswitches, in particular the absorption maxima and the half-life. For photopharmacological applications, photoswitches should ideally be operated by visible light in at least one direction, and feature a metastable isomer with a half-life of 0.1–10 seconds. Here we present our efforts towards the engineering of the half-life of iminothioindoxyl (ITI) photoswitches, a recently discovered class of visible-light-responsive photochromes, whose applicability was hitherto limited by half-lives in the low millisecond range. Through the synthesis and characterization of a library of ITI photoswitches, we discovered variants with a substantially increased thermal stability, reaching half-lives of up to 0.2 seconds. Based on spectroscopic and computational analyses, we demonstrate how different substituent positions on the ITI molecule can be used to tune its photophysical properties independently to fit the desired application. Additionally, the unique reactivity of the ITI derivative that featured a perfluoro-aromatic ring and had the most long-lived metastable state was shown to be useful for labeling of nucleophilic functional groups. The present research thus paves the way for using ITI photoswitches in photopharmacology and chemical biology.
dc.description.sponsorshipAPVV-20-0098 Svetlom riadené molekulové prepínanie Ministerstvo školstva, mládeže a telovýchovy ČR 90254 e-INFRA CZ TAČR CZ.02.01.01/00/22_008/0004587 TECHSCALE: Technologie za hranicí nanosvěta
dc.identifier.doihttps://doi.org/10.1039/D4SC01457J
dc.identifier.issn2041-6520
dc.identifier.issn2041-6539
dc.identifier.urihttps://repo.umb.sk/handle/123456789/1048
dc.language.isoen
dc.publisherRoyal Society of Chemistry : Cambridge
dc.rightsCC BY Creative Commons Attribution 4.0. International
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectsvetlo
dc.subjectfyzikálne vlastnosti
dc.subjectfotofarmakológia
dc.subjectphotopharmacology
dc.titleGetting a molecular grip on the half-lives of iminothioindoxyl photoswitches
dc.typeArticle
dc.typeinfo:eu-repo/semantics/article

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