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

45 Citations (Scopus)
107 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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