4.8 Article

General Principles for the Design of Visible-Light-Responsive Photoswitches: Tetra-ortho-Chloro-Azobenzenes

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 48, 页码 21663-21670

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202008700

关键词

azobenzene; photochromism; photoswitches; TD-DFT; visible light

资金

  1. Netherlands Organization for Scientific Research (NWO-CW), ECHO grant [711.017.012]
  2. Region des Pays de la Loire
  3. Scientific Grant Agency VEGA [1/0562/20]
  4. Ministry of Science and Education (FMS gravitation program)
  5. Humboldt Foundation

向作者/读者索取更多资源

Molecular photoswitches enable reversible external control of biological systems, nanomachines, and smart materials. Their development is driven by the need for low energy (green-red-NIR) light switching, to allow non-invasive operation with deep tissue penetration. The lack of clear design principles for the adaptation and optimization of such systems limits further applications. Here we provide a design rulebook for tetra-ortho-chloroazobenzenes, an emerging class of visible-light-responsive photochromes, by elucidating the role that substituents play in defining their key characteristics: absorption spectra, band overlap, photoswitching efficiencies, and half-lives of the unstable cis isomers. This is achieved through joint photochemical and theoretical analyses of a representative library of molecules featuring substituents of varying electronic nature. A set of guidelines is presented that enables tuning of properties to the desired application through informed photochrome engineering.

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