Synthesis and fluorescence properties of 2-aryl-3-hydroxyquinolones, a new class of dyes displaying dual fluorescence

被引：49

作者：

Yushchenko, DA ^{[1
]}

Bilokin', MD

Pyvovarenko, OV

Duportail, G

Mély, Y

Pivovarenko, VG

机构：

[1] Kiev Natl Taras Shevchenko Univ, Dept Chem, UA-01033 Kiev, Ukraine

[2] Univ Louis Pasteur Strasbourg 1, Fac Pharm, Inst Gilbert Laustriat, CNRS,LCI,UMR 7175, F-67401 Illkirch Graffenstaden, France

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 06期

关键词：

3-hydroxyquinolones; absorption; fluorescence probes; polarity sensors;

D O I：

10.1016/j.tetlet.2005.11.160

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 2-aryl-3-hydroxyquinolones (3HQs) with different electron donating aryl substituents at the position 2 were synthesized. Their absorption and fluorescence properties were studied in solvents of medium and high polarity. Almost all the synthesized 3HQs display dual fluorescence in the tested solvents, in line with an excited state intramolecular proton transfer reaction. For N-methyl substituted compounds, the intensity ratio of the two emission bands was found to be exquisitely sensitive to solvent polarity, with a two orders of magnitude change from toluene to dimethylsulfoxide. Consequently, these compounds appear as prospective polarity fluorescent labels for proteins and nucleic acids. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：905 / 908

页数：4

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