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

Autor: Kortekaas L; Center for Soft Nanoscience and Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster Busso-Peus-Straße 10 48149 Münster Germany kortekaas@uni-muenster.de b.j.ravoo@uni-muenster.de., Simke J; Center for Soft Nanoscience and Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster Busso-Peus-Straße 10 48149 Münster Germany kortekaas@uni-muenster.de b.j.ravoo@uni-muenster.de., Arndt NB; Center for Soft Nanoscience and Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster Busso-Peus-Straße 10 48149 Münster Germany kortekaas@uni-muenster.de b.j.ravoo@uni-muenster.de., Böckmann M; Institute for Solid State Theory and Center for Multiscale Theory & Computation, Westfälische Wilhelms-Universität Münster Wilhelm-Klemm-Str. 10 48149 Münster Germany., Doltsinis NL; Institute for Solid State Theory and Center for Multiscale Theory & Computation, Westfälische Wilhelms-Universität Münster Wilhelm-Klemm-Str. 10 48149 Münster Germany., Ravoo BJ; Center for Soft Nanoscience and Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster Busso-Peus-Straße 10 48149 Münster Germany kortekaas@uni-muenster.de b.j.ravoo@uni-muenster.de.
Jazyk: angličtina
Zdroj: Chemical science [Chem Sci] 2021 Jul 19; Vol. 12 (34), pp. 11338-11346. Date of Electronic Publication: 2021 Jul 19 (Print Publication: 2021).
DOI: 10.1039/d1sc03308e
Abstrakt: 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 p K a of the applied acid is sufficiently low. The tuning of isomerisation kinetics from days to seconds by the p K 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.
Competing Interests: There are no conflicts to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE
Externí odkaz: