Arylazobenzimidazoles: versatile visible-light photoswitches with tuneable Z -isomer stability.

Autor:	Steinmüller SAM; Pharmazeutische und Medizinische Chemie, Institut für Pharmazie und Lebensmittelchemie, Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany michael.decker@uni-wuerzburg.de., Odaybat M; Department of Chemistry, Molecular Sciences Research Hub, White City Campus, Imperial College London London W12 0BZ UK m.fuchter@imperial.ac.uk., Galli G; Pharmazeutische und Medizinische Chemie, Institut für Pharmazie und Lebensmittelchemie, Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany michael.decker@uni-wuerzburg.de., Prischich D; Department of Chemistry, Molecular Sciences Research Hub, White City Campus, Imperial College London London W12 0BZ UK m.fuchter@imperial.ac.uk., Fuchter MJ; Department of Chemistry, Molecular Sciences Research Hub, White City Campus, Imperial College London London W12 0BZ UK m.fuchter@imperial.ac.uk., Decker M; Pharmazeutische und Medizinische Chemie, Institut für Pharmazie und Lebensmittelchemie, Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany michael.decker@uni-wuerzburg.de.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2024 Mar 05; Vol. 15 (14), pp. 5360-5367. Date of Electronic Publication: 2024 Mar 05 (Print Publication: 2024).
DOI:	10.1039/d3sc05246j
Abstrakt:	Benzimidazole heterocycles are of great importance in medicinal chemistry due to their applicability to a wide range of pharmacological targets, therefore representing a prototypical "privileged structure". In photopharmacology, azoheteroarene photoswitches have emerged as valuable tools for a variety of applications due to the high tuneability of their photophysical properties. Benzimidazole-based photoswitches could therefore enable the optically-controlled investigation of many pharmacological targets and find application in materials science. Here we report a combined experimental and computational investigation of such arylazobenzimidazoles, which allowed us to identify derivatives with near-quantitative bidirectional photoswitching using visible light and highly tuneable Z -isomer stability. We further demonstrate that arylazobenzimidazoles bearing a free benzimidazole N-H group not only exhibit efficient bidirectional photoswitching, but also excellent thermal Z -isomer stability, contrary to previously reported fast-relaxing Z -isomers of N-H azoheteroarenes. Finally, we describe derivatives which can be reversibly isomerized with cyan and red light, thereby enabling significantly "red-shifted" photocontrol over prior azoheteroarenes. The understanding gained in this study should enable future photopharmacological efforts by employing photoswitches based on the privileged benzimidazole structure. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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