Substituent Effects on 3-Arylazoindole Photoswitches

The Journal of Organic Chemistry
Nadja A SimethBurkhard König

Abstract

The development and investigation of heteroazo switches has flourished in recent years. Because of their specific photophysical and photochemical properties, they find versatile applications from material science to medicine. However, a deep mechanistic understanding is needed to be able to predict the properties of such azoswitches. In particular, the effect of different substituents on the azo chromophore is of great interest as they are often crucial for embedding the molecular switch into a system of interest. Herein, we provide a detailed spectroscopic and computational study on the influence of substituents on 3-phenylazoindoles chosen as models. We will point out changes in absorption properties and analyze the photostationary state of the thermally labile Z isomers through computational means to provide a general structure-property relationship guideline for further use of these compounds.

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Citations

Feb 13, 2020·Organic & Biomolecular Chemistry·J A Balam-VillarrealM C Ortega-Alfaro
May 14, 2020·Organic Letters·Zhichao LuGerald B Hammond
Feb 20, 2020·The Journal of Organic Chemistry·Karin RustlerBurkhard König
Jul 7, 2020·The Journal of Physical Chemistry Letters·Borys OśmiałowskiDenis Jacquemin
Mar 26, 2020·Journal of the American Chemical Society·David B KonradAhmed M Ali
Feb 15, 2020·The Journal of Organic Chemistry·Ricardo A AngnesGerald B Hammond
Oct 1, 2021·Chemical Society Reviews·Jana VolarićBen L Feringa

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