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Acid-catalysed liquid-to-solid transitioning of arylazoisoxazole photoswitches.

ABSTRACT: Molecular photoswitches play a vital role in the development of responsive materials. These molecular building blocks are particularly attractive when multiple stimuli can be combined to bring about physical changes, sometimes leading to unexpected properties and functions. The arylazoisoxazole molecular switch was recently shown to be capable of efficient photoreversible solid-to-liquid phase transitions with application in photoswitchable surface adhesion. Here, we show that the arylazoisoxazole forms thermally stable and photoisomerisable protonated Z- and E-isomers in an apolar aprotic solvent when the pK _a of the applied acid is sufficiently low. The tuning of isomerisation kinetics from days to seconds by the pK _a of the acid not only opens up new reactivity in solution, but also the solid-state photoswitching of azoisoxazoles can be efficiently reversed with selected acid vapours, enabling acid-gated photoswitchable surface adhesion.

SUBMITTER: Kortekaas L

PROVIDER: S-EPMC8447883 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Acid-catalysed liquid-to-solid transitioning of arylazoisoxazole photoswitches.

Kortekaas Luuk L Simke Julian J Arndt Niklas B NB Böckmann Marcus M Doltsinis Nikos L NL Ravoo Bart Jan BJ

Chemical science 20210719 34

Molecular photoswitches play a vital role in the development of responsive materials. These molecular building blocks are particularly attractive when multiple stimuli can be combined to bring about physical changes, sometimes leading to unexpected properties and functions. The arylazoisoxazole molecular switch was recently shown to be capable of efficient photoreversible solid-to-liquid phase transitions with application in photoswitchable surface adhesion. Here, we show that the arylazoisoxazo ...[more]

PMID: 34667544

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