Synthesis and switching properties of new derivatives of azoresveratrol

Jérôme Berthet; Laurence Agouridas; Siyao Chen; Hassan Allouchi; Patricia Melnyk; Benoît Champagne; Stéphanie Delbaere

doi:10.1016/j.dyepig.2019.107666

Synthesis and switching properties of new derivatives of azoresveratrol

Jérôme Berthet, Laurence Agouridas, Siyao Chen, Hassan Allouchi, Patricia Melnyk, Benoît Champagne, Stéphanie Delbaere

Research output: Contribution to journal › Article › peer-review

Abstract

The synthesis and response upon light irradiation of azoresveratrol and six derivatives are reported. While UV irradiation of para-hydroxy trans compounds leads to thermally unstable cis isomers, the para-methoxy and the para-phosphoric ester substituents result in reaching a high conversion and increasing the thermal stability. In addition, the phosphoric ester azo derivative presents similar properties in organic and aqueous solutions, opening the way towards biological applications.

Original language	English
Article number	107666
Number of pages	9
Journal	Dyes and pigments
Volume	171
DOIs	https://doi.org/10.1016/j.dyepig.2019.107666
Publication status	Published - 1 Dec 2019

Keywords

Azobenzene
DFT calculations
NMR
Photoswitching
Thermal relaxation
UV irradiation

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10.1016/j.dyepig.2019.107666

Cite this

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title = "Synthesis and switching properties of new derivatives of azoresveratrol",

abstract = "The synthesis and response upon light irradiation of azoresveratrol and six derivatives are reported. While UV irradiation of para-hydroxy trans compounds leads to thermally unstable cis isomers, the para-methoxy and the para-phosphoric ester substituents result in reaching a high conversion and increasing the thermal stability. In addition, the phosphoric ester azo derivative presents similar properties in organic and aqueous solutions, opening the way towards biological applications.",

keywords = "Azobenzene, DFT calculations, NMR, Photoswitching, Thermal relaxation, UV irradiation",

author = "J{\'e}r{\^o}me Berthet and Laurence Agouridas and Siyao Chen and Hassan Allouchi and Patricia Melnyk and Beno{\^i}t Champagne and St{\'e}phanie Delbaere",

note = "Funding Information: The calculations were performed on the computing facilities of the Consortium des {\'E}quipements de Calcul Intensif (C{\'E}CI, http://www.ceci-hpc.be ), and particularly those of the Technological Platform on High-Performance Computing located at UNamur ( http://www.ptci.unamur.be ), for which the authors gratefully acknowledge the financial support of the FNRS-FRFC , of the Walloon Region, and of the University of Namur. Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd Copyright: Copyright 2019 Elsevier B.V., All rights reserved.",

year = "2019",

month = dec,

day = "1",

doi = "10.1016/j.dyepig.2019.107666",

language = "English",

volume = "171",

journal = "Dyes and pigments",

issn = "0143-7208",

publisher = "Elsevier",

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TY - JOUR

T1 - Synthesis and switching properties of new derivatives of azoresveratrol

AU - Berthet, Jérôme

AU - Agouridas, Laurence

AU - Chen, Siyao

AU - Allouchi, Hassan

AU - Melnyk, Patricia

AU - Champagne, Benoît

AU - Delbaere, Stéphanie

N1 - Funding Information: The calculations were performed on the computing facilities of the Consortium des Équipements de Calcul Intensif (CÉCI, http://www.ceci-hpc.be ), and particularly those of the Technological Platform on High-Performance Computing located at UNamur ( http://www.ptci.unamur.be ), for which the authors gratefully acknowledge the financial support of the FNRS-FRFC , of the Walloon Region, and of the University of Namur. Publisher Copyright: © 2019 Elsevier Ltd Copyright: Copyright 2019 Elsevier B.V., All rights reserved.

PY - 2019/12/1

Y1 - 2019/12/1

N2 - The synthesis and response upon light irradiation of azoresveratrol and six derivatives are reported. While UV irradiation of para-hydroxy trans compounds leads to thermally unstable cis isomers, the para-methoxy and the para-phosphoric ester substituents result in reaching a high conversion and increasing the thermal stability. In addition, the phosphoric ester azo derivative presents similar properties in organic and aqueous solutions, opening the way towards biological applications.

AB - The synthesis and response upon light irradiation of azoresveratrol and six derivatives are reported. While UV irradiation of para-hydroxy trans compounds leads to thermally unstable cis isomers, the para-methoxy and the para-phosphoric ester substituents result in reaching a high conversion and increasing the thermal stability. In addition, the phosphoric ester azo derivative presents similar properties in organic and aqueous solutions, opening the way towards biological applications.

KW - Azobenzene

KW - DFT calculations

KW - NMR

KW - Photoswitching

KW - Thermal relaxation

KW - UV irradiation

UR - http://www.scopus.com/inward/record.url?scp=85067876930&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2019.107666

DO - 10.1016/j.dyepig.2019.107666

M3 - Article

AN - SCOPUS:85067876930

SN - 0143-7208

VL - 171

JO - Dyes and pigments

JF - Dyes and pigments

M1 - 107666

ER -

Synthesis and switching properties of new derivatives of azoresveratrol

Abstract

Keywords

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Other files and links

Fingerprint

CÉCI – Consortium of high performance computing centers

consortium des équipements de calcul intensif

High Performance Computing Technology Platform

CCDC 1897318: Experimental Crystal Structure Determination

CCDC 1897319: Experimental Crystal Structure Determination

Cite this

Synthesis and switching properties of new derivatives of azoresveratrol

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Projects

CÉCI – Consortium of high performance computing centers

consortium des équipements de calcul intensif

Equipment

High Performance Computing Technology Platform

Datasets

CCDC 1897318: Experimental Crystal Structure Determination

CCDC 1897319: Experimental Crystal Structure Determination

Cite this