Synthesis and switching properties of new derivatives of azoresveratrol

被引：7
作者：
Berthet, Jerome [1 ]
Agouridas, Laurence [2 ]
Chen, Siyao [2 ]
Allouchi, Hassan [3 ]
Melnyk, Patricia [2 ]
Champagne, Benoit [4 ]
Delbaere, Stephanie [1 ]
机构：
[1] Univ Lille, LASIR Lab Spectrochim Infra Rouge & Roman, CNRS, UMR 8516, F-59000 Lille, France
[2] Univ Lille, Ctr Rech Jean Pierre Aubert Neurosci & Canc, CHU Lille, INSERM,JPArc,UMR S 1172, F-59000 Lille, France
[3] Univ Tours, Fac Pharm, EA SIMBA Lab Chim Phys 7502, 31 Ave Monge, F-37200 Tours, France
[4] Univ Namur, Theoret & Struct Phys Chem Unit, Lab Theoret Chem, Namur Inst Struct Matter, Rue Bruxelles 61, B-5000 Namur, Belgium
来源：
DYES AND PIGMENTS | 2019年 / 171卷
关键词：
Azobenzene; Photoswitching; Thermal relaxation; UV irradiation; NMR; DFT calculations; TO-TRANS ISOMERIZATION; THERMAL CIS; AZOBENZENE DERIVATIVES; MECHANISM; SOLVENT; RESVERATROL; SUBSTITUENT; STABILITY; PROOF;
D O I：
10.1016/j.dyepig.2019.107666
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
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.
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页数：9
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共 56 条
  • [31] 113 The cis-form of azobenzene and the velocity of the thermal cis -> trans-conversion of azobenzene and some derivatives
    Hartley, GS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1938, : 633 - 642
  • [32] Photochromism of Diarylethene Molecules and Crystals: Memories, Switches, and Actuators
    Irie, Masahiro
    Fulcaminato, Tuyoshi
    Matsuda, Kenji
    Kobatake, Seiya
    [J]. CHEMICAL REVIEWS, 2014, 114 (24) : 12174 - 12277
  • [33] Resveratrol and Amyloid-Beta: Mechanistic Insights
    Jia, Yongming
    Wang, Na
    Liu, Xuewei
    [J]. NUTRIENTS, 2017, 9 (10):
  • [34] Knoll H., 2004, CRC Handbook of organic photochemistry and photobiology, V2nd, P1
  • [35] Effect of solvent on cis-to-trans isomerization of 4-hydroxyazobenzene aggregated through intermolecular hydrogen bonds
    Kojima, M
    Nebashi, S
    Ogawa, K
    Kurita, N
    [J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (10) : 994 - 1000
  • [36] Density functional molecular orbital calculations on the stability of hydrogen-bonded 4-hydroxyazobenzene dimers
    Kurita, N
    Nebashi, S
    Kojima, M
    [J]. CHEMICAL PHYSICS LETTERS, 2005, 408 (4-6) : 197 - 204
  • [37] THE EFFECTS OF SUBSTITUENTS AND SOLVENTS ON THE CIS-]TRANS CHANGE OF AZOBENZENE
    LEFEVRE, RJW
    NORTHCOTT, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1953, (MAR): : 867 - 870
  • [38] Design of a Highly Bistable Photoswitchable Tethered Ligand for Rapid and Sustained Manipulation of Neurotransmission
    Lin, Wan-Chen
    Tsai, Ming-Chi
    Rajappa, Rajit
    Kramer, Richard H.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (24) : 7445 - 7448
  • [39] PHOTOCHEMISTRY OF STILBENES .3. SOME ASPECTS OF MECHANISM OF PHOTOCYCLIZATION TO PHENANTHRENES
    MALLORY, FB
    WOOD, CS
    GORDON, JT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (15) : 3094 - &
  • [40] Azo-hydrazone tautomerism in protonated aminoazobenzenes: Resonance Raman spectroscopy and quantum-chemical calculations
    Matazo, Deborah R. C.
    Ando, Romulo A.
    Borin, Antonio C.
    Santos, Paulo S.
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2008, 112 (19) : 4437 - 4443
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