Novel coumarin fluorescent dyes: Synthesis, structural characterization and recognition behavior towards Cu(II) and Ni(II)

被引:94
作者
Li, Hongqi [1 ]
Cai, Li [1 ]
Li, Jinxing [1 ]
Hu, Yixin [1 ]
Zhou, Pingping [1 ]
Zhang, Jiming [1 ]
机构
[1] Donghua Univ, Key Lab Sci & Technol Ecotext, Minist Educ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China
关键词
Fluorescent; Coumarin; Dye; Recognition; Cu(II) ion; Ni(II) ion; SENSOR; PROBE; CHEMOSENSORS; DERIVATIVES; CYANIDE; PH;
D O I
10.1016/j.dyepig.2011.05.011
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A series of novel coumarin dyes (3-12) were designed and synthesized. The structures of the dyes were characterized by IR, H-1 NMR, C-13 NMR, F-19 NMR, MS and single crystal X-ray diffraction. 3-(2-Benzoylhydrazonotrifluoroethyl)-7-(N,N-diethylamino)coumarin (11) could recognize Cu2+ and Ni2+ selectively in aqueous solution. Upon addition of Cu2+ or Ni2+ to 11 a blue shift or a bathochromatic shift of the absorption band was observed while the emission band blue-shifted with decrease in the fluorescence intensity. Upon addition of Cu2+ the color of the solution of 11 changed from orange to red. The results showed that 11 could be used as an optical chemosensor of Cu2+ and Ni2+. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:309 / 316
页数:8
相关论文
共 41 条
[1]   Hydrogen-transfer reactions from phenols to TEMPO prefluorescent probes in micellar systems [J].
Aliaga, Carolina ;
Juarez-Ruiz, Juan M. ;
Scaiano, J. C. ;
Aspee, Alexis .
ORGANIC LETTERS, 2008, 10 (11) :2147-2150
[2]   Magnesium optical one-shot sensor based on a coumarin chromoionophore [J].
Capitán-Vallvey, LE ;
Fernández-Ramos, MD ;
Lapresta-Fernández, A ;
Brunet, E ;
Rodríguez-Ubis, JC ;
Juanes, O .
TALANTA, 2006, 68 (05) :1663-1670
[3]   Phosphorus-supported multidentate coumarin-containing fluorescence sensors for Cu2+ [J].
Chandrasekhar, Vadapalli ;
Bag, Prasenjit ;
Pandey, Mrituanjay D. .
TETRAHEDRON, 2009, 65 (47) :9876-9883
[4]   The first synthesis of 4-unsubstituted 3-(trifluoroacetyl)coumarins by the Knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate followed by chromene-coumarin recyclization [J].
Chizhov, Dmitrii L. ;
Sosnovskikh, Vyacheslav Ya. ;
Pryadeina, Marina V. ;
Burgart, Yanina V. ;
Saloutin, Victor I. ;
Charushin, Valery N. .
SYNLETT, 2008, (02) :281-285
[5]   Synthesis and spectral characteristics of fluorescent dyes based on coumarin fluorophore and hindered amine stabilizer in solution and polymer matrices [J].
Danko, Martin ;
Szabo, Erik ;
Hrdlovic, Pavol .
DYES AND PIGMENTS, 2011, 90 (02) :129-138
[6]   Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore [J].
Du, Lupei ;
Li, Minyong ;
Zheng, Shilong ;
Wang, Binghe .
TETRAHEDRON LETTERS, 2008, 49 (19) :3045-3048
[7]   Ratiometric fluorescence chemosensors for copper(II) and mercury(II) based on FRET systems [J].
He, Guangjie ;
Zhang, Xiaolin ;
He, Cheng ;
Zhao, Xiuwen ;
Duan, Chunying .
TETRAHEDRON, 2010, 66 (51) :9762-9768
[8]   Development of a library of 6-arylcoumarins as candidate fluorescent sensors [J].
Hirano, Tomoya ;
Hiromoto, Kenichi ;
Kagechika, Hiroyuki .
ORGANIC LETTERS, 2007, 9 (07) :1315-1318
[9]   A fluorescence resonance energy transfer probe for sensing pH in aqueous solution [J].
Hong, Sung Woo ;
Jo, Won Ho .
POLYMER, 2008, 49 (19) :4180-4187
[10]   Highly sensitive and selective fluorescent chemosensor for Ag+ based on a coumarin-Se2N chelating conjugate [J].
Huang, Shanshan ;
He, Song ;
Lu, Yan ;
Wei, Fangfang ;
Zeng, Xianshun ;
Zhao, Liancheng .
CHEMICAL COMMUNICATIONS, 2011, 47 (08) :2408-2410