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Conformation of Novel Azo-Dyes Bearing End-Capped Oligo(ethylene glycol) Studied by UV–vis and NMR Spectroscopy

Abstract : Two novel azo-dyes bearing an end-capped oligo(ethylene glycol) chain were synthesized and then studied by UV–visible and NMR spectroscopy. For both azobenzenes, the end-capped oligo(ethylene glycol) segment is on the para position of the first phenyl ring. On the second phenyl ring, a methoxy group is added on the para position for one azo-dye and no substitution group on the other, which made them electronically a push–push and a push system, respectively. The presence of the methoxy group changes significantly the absorption and the photoisomerization behaviors and results in a much less intense absorbance for the trans isomer and a shift from 350 to 360 nm. In the kinetic studies the azobenzene bearing a methoxy group shows a zero-order and a first-order kinetics as a function of the time scale of the study as well as an aggregation phenomenon. This azo-dye in different solvents has been studied by 1H NMR and pulsed gradient NMR experiments to understand the effects of the photoisomerization and the aggregation on the self-diffusion of these molecules in solutions.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02875456
Contributor : Cassandre Kouvatas <>
Submitted on : Friday, June 19, 2020 - 4:51:33 PM
Last modification on : Monday, July 20, 2020 - 12:34:52 PM

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Cassandre Kouvatas, Wilms Baille, Jesús Ortíz-Palacios, Edgar Aguilar-Ortíz, Ernesto Rivera, et al.. Conformation of Novel Azo-Dyes Bearing End-Capped Oligo(ethylene glycol) Studied by UV–vis and NMR Spectroscopy. Journal of Physical Chemistry B, American Chemical Society, 2015, 119 (37), pp.12318-12324. ⟨10.1021/acs.jpcb.5b05853⟩. ⟨hal-02875456⟩

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