N,N′-Disubstituted Indigos as Readily Available Red-Light Photoswitches with Tunable Thermal Half-Lives

Aurelio Bonasera, Denis Jacquemin, Aurelio Bonasera, Yves Garmshausen, Chung-Yang Huang, Lachezar Hristov, Bernd M. Schmidt, Stefan Hecht

Risultato della ricerca: Articlepeer review

42 Citazioni (Scopus)

Abstract

Some rare indigo derivatives have been known for a long time to be photochromic upon irradiation with red light, which should be advantageous for many applications. However, the absence of strategies to tune their thermal half-lives by modular molecular design as well as the lack of proper synthetic methods to prepare a variety of such molecules from the parent indigo dye have so far precluded their use. In this work, several synthetic protocols for N-functionalization have been developed, and a variety of N-alkyl and N-aryl indigo derivatives have been prepared. By installation of electron-withdrawing substituents on the N-aryl moieties, the thermal stability of the Z-isomers could be enhanced while maintaining the advantageous photoswitching properties upon irradiation with red light (660 nm LED). Both experimental data and computational results suggest that the ability to tune thermal stability without affecting the dyes' absorption maxima originates from the twisted geometry of the N-aryl groups. The new indigo photoswitches reported are expected to have a large impact on the development of optical methods and applications in both life and material sciences.
Lingua originaleEnglish
pagine (da-a)15205-15211
Numero di pagine7
RivistaJournal of the American Chemical Society
Volume139
Stato di pubblicazionePublished - 2017

All Science Journal Classification (ASJC) codes

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  • ???subjectarea.asjc.1600.1600???
  • ???subjectarea.asjc.1300.1303???
  • ???subjectarea.asjc.1500.1505???

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