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Issue 21, 2020
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Non-photoisomerizable butterfly shaped tetrasubstituted azobenzenes: synthesis and photophysical studies

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Abstract

The trans-azobenzene (AB) substituted derivatives with bulky carbazole (1), phenothiazine (2), and phenyl (3) have been synthesized to understand the effect of steric crowding around the –N[double bond, length as m-dash]N– linkage on the photoisomerization process. The substituents maintain orthogonality to the azobenzene plane and the electronic properties exhibit a combination of individual chromophores. Irradiation of 1 and 2 with various light sources including a 365 nm pen-ray lamp, and a 150 W Xe–Hg lamp, and even exposure to sunlight for a week does not yield the cis isomer revealing the exceptional photostability of the synthesized azobenzene derivatives. These studies suggest that possessing steric crowding around the azo linkage would be a potential strategy to develop photostable azobenzene-based functional materials.

Graphical abstract: Non-photoisomerizable butterfly shaped tetrasubstituted azobenzenes: synthesis and photophysical studies

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Supplementary files

Article information


Submitted
03 Mar 2020
Accepted
05 May 2020
First published
05 May 2020

New J. Chem., 2020,44, 8818-8822
Article type
Paper

Non-photoisomerizable butterfly shaped tetrasubstituted azobenzenes: synthesis and photophysical studies

A. Raman, A. U. Neelambra, V. Karunakaran and S. Easwaramoorthi, New J. Chem., 2020, 44, 8818
DOI: 10.1039/D0NJ01092H

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