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

Lucien N LameijerSimon BudzakNadja A SimethMickel J HansenBen L FeringaDenis JacqueminWiktor Szymanski
Published in: Angewandte Chemie (International ed. in English) (2020)
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.
Keyphrases
  • visible light
  • cancer therapy
  • cross sectional
  • photodynamic therapy
  • single molecule
  • drug delivery
  • density functional theory
  • fluorescent probe