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Issue 4, 2017
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A theoretical study on the thermal cistrans isomerization of azoheteroarene photoswitches

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Abstract

Quantum chemical calculations of a novel class of five-membered azo photoswitches arylazopyrazoles have been carried out with the aim of describing the photochemical properties of their thermal cistrans isomerization. The effects of substituents, in particular their number, position and nature of the electron donating groups (EDGs), on activation energies have been systematically researched with the ultimate goal of illuminating the isomerization process. It is found that all parameters are highly dependent on the substitution pattern on the heteroarene, allowing a planar or twisted geometry, which in turn has a significant impact on the absorption spectra, the energy levels of molecular orbitals, the transition properties of the trans/cis isomers, the half-lives and the rate constants for the thermal cistrans isomerization of the compounds. The nature of the transition state(s) and its dependence on substituents and the environment are discussed. Energy barriers were determined from two-dimensional potential energy surfaces of the ground states.

Graphical abstract: A theoretical study on the thermal cis–trans isomerization of azoheteroarene photoswitches

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Article information


Submitted
04 Oct 2016
Accepted
05 Jan 2017
First published
06 Jan 2017

New J. Chem., 2017,41, 1659-1669
Article type
Paper

A theoretical study on the thermal cistrans isomerization of azoheteroarene photoswitches

T. Yin, Z. Zhao and H. Zhang, New J. Chem., 2017, 41, 1659
DOI: 10.1039/C6NJ03095E

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