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

Lucien N. Lameijer, Simon Budzak, Nadja A. Simeth, Mickel J. Hansen, Ben L. Feringa, Denis Jacquemin*, Wiktor Szymanski*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

4 Citations (Scopus)
35 Downloads (Pure)

Abstract

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.

Original languageEnglish
Pages (from-to)21663-21670
Number of pages8
JournalAngewandte Chemie-International Edition
Volume59
Issue number48
DOIs
Publication statusPublished - 23-Nov-2020

Keywords

  • azobenzene
  • photochromism
  • photoswitches
  • TD-DFT
  • visible light
  • OPTICAL CONTROL
  • SHEDDING LIGHT
  • IN-VIVO
  • PHOTOISOMERIZATION
  • FLUOROAZOBENZENES
  • PHOTOCHROMISM
  • INHIBITORS
  • SWITCHES

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