Water-Soluble Arylazoisoxazole Photoswitches.

Autor: Höglsperger F; Organisch-Chemisches Institut and Center for Soft Nanoscience, Westfälische Wilhelms-Universität Münster, Correnstrasse 36, 48149, Münster, Germany., Larik FA; School of Chemistry, The University of New South Wales, Sydney, NSW-2052, Australia., Bai C; School of Chemistry, The University of New South Wales, Sydney, NSW-2052, Australia.; UNSW RNA Institute, The University of New South Wales, Sydney, NSW-2052, Australia., Seyfried MD; Organisch-Chemisches Institut and Center for Soft Nanoscience, Westfälische Wilhelms-Universität Münster, Correnstrasse 36, 48149, Münster, Germany., Daniliuc C; Organisch-Chemisches Institut and Center for Soft Nanoscience, Westfälische Wilhelms-Universität Münster, Correnstrasse 36, 48149, Münster, Germany., Klaasen H; Organisch-Chemisches Institut and Center for Soft Nanoscience, Westfälische Wilhelms-Universität Münster, Correnstrasse 36, 48149, Münster, Germany., Thordarson P; School of Chemistry, The University of New South Wales, Sydney, NSW-2052, Australia.; UNSW RNA Institute, The University of New South Wales, Sydney, NSW-2052, Australia., Beves JE; School of Chemistry, The University of New South Wales, Sydney, NSW-2052, Australia., Ravoo BJ; Organisch-Chemisches Institut and Center for Soft Nanoscience, Westfälische Wilhelms-Universität Münster, Correnstrasse 36, 48149, Münster, Germany.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2023 Nov 21; Vol. 29 (65), pp. e202302069. Date of Electronic Publication: 2023 Oct 11.
DOI: 10.1002/chem.202302069
Abstrakt: Azoheteroarenes are emerging as powerful alternatives to azobenzene molecular photoswitches. In this study, water-soluble arylazoisoxazole photoswitches are introduced. UV/vis and NMR spectroscopy revealed moderate to very good photostationary states and reversible photoisomerization between the E- and Z-isomers over multiple cycles with minimal photobleaching. Several arylazoisoxazoles form host-guest complexes with β- and γ-cyclodextrin with significant differences in binding constants for each photoisomer as shown by isothermal titration calorimetry and NMR experiments, indicating their potential for photoresponsive host-guest chemistry in water. One carboxylic acid functionalized arylazoisoxazole can act as a hydrogelator, allowing gel properties to be manipulated reversibly with light. The hydrogel was characterized by rheological experiments, atom force microscopy and transmission electron microscopy. These results demonstrate that arylazoisoxazoles can find applications as molecular photoswitches in aqueous media.
(© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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