Fluorescence turn on of coumarin derivatives by metal cations: A new signaling mechanism based on C=N isomerization

被引：578

作者：

Wu, Jia-Sheng ^{[1
]}

Liu, Wei-Min

Zhuang, Xiao-Qing

Wang, Fang

Wang, Peng-Fei

Tao, Si-Lu

Zhang, Xiao-Hong

Wu, Shi-Kang

Lee, Shuit-Tong

机构：

[1] Chinese Acad Sci, Lab Organ Optoelect Funct Mat & Mol Engn, Nanoorgan Photoelect Lab, Beijing 100080, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100080, Peoples R China

[3] City Univ Hong Kong, Ctr Super Diamond & Adv Films, Hong Kong, Hong Kong, Peoples R China

[4] City Univ Hong Kong, Dept Phys & Mat Sci, Hong Kong, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 01期

关键词：

D O I：

10.1021/ol062518z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new sensing mechanism based on C = N isomerization, which shows a very significant fluorescence enhancement to the metal cations in a simple and efficient way, is demonstrated. A coumarin derivative (L) containing a C = N group was designed as an example for illustration. The free ligand L is almost nonfluorescent due to the isomerization of CN double bond in the excited state. However, the solution of ligand shows about a 200-fold increase of fluorescence quantum yield (about 30%) upon addition of Zn(ClO4)(2).

引用

页码：33 / 36

页数：4

共 41 条

[11] Site-selective binding and dual mode recognition of serum albumin by a squaraine dye [J].

Jisha, Vadakkancheril S. ;

Arun, Kalliat T. ;

Hariharan, Mahesh ;

Ramaiah, Danaboyina .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (18) :6024-6025

[12] Mechanisms of acid-catalyzed Z/E isomerization of imines [J].

Johnson, JE ;

Morales, NM ;

Gorczyca, AM ;

Dolliver, DD ;

McAllister, MA .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7979-7985

[13] Zinc sensing for cellular application [J].

Kikuchi, K ;

Komatsu, K ;

Nagano, T .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2004, 8 (02) :182-191

[14] Dinuclear ruthenium(II) polypyridyl complexes containing large, redox-active, aromatic bridging ligands: Synthesis, characterization, and intramolecular quenching of MLCT excited states [J].

Kim, MJ ;

Konduri, R ;

Ye, HW ;

MacDonnell, FM ;

Puntoriero, F ;

Serroni, S ;

Campagna, S ;

Holder, T ;

Kinsel, G ;

Rajeshwar, K .

INORGANIC CHEMISTRY, 2002, 41 (09) :2471-2476

[15] A new fluorescent PET chemosensor for fluoride ions [J].

Kim, SK ;

Yoon, J .

CHEMICAL COMMUNICATIONS, 2002, (07) :770-771

[16] Development of a ratiometric fluorescent zinc ion probe in near-infrared region, based on tricarbocyanine chromophore [J].

Kiyose, Kazuki ;

Kojima, Hirotatsu ;

Urano, Yasuteru ;

Nagano, Tetsuo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (20) :6548-6549

[17] A 3-hydroxychromone with dramatically improved fluorescence properties [J].

Klymchenko, AS ;

Ozturk, T ;

Pivovarenko, VG ;

Demchenko, AP .

TETRAHEDRON LETTERS, 2001, 42 (45) :7967-7970

[18]

Li Z., 1997, J. Fluoresc., V7, P237, DOI DOI 10.1007/BF02758224

[19] Illuminating zinc in biological systems [J].

Lim, NC ;

Freake, HC ;

Brückner, C .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (01) :38-49

[20] Fluorogenic and chromogenic chemosensors and reagents for anions [J].

Martínez-Máñez, R ;

Sancenón, F .

CHEMICAL REVIEWS, 2003, 103 (11) :4419-4476

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