A new imidazolium acridine derivative as fluorescent chemosensor for pyrophosphate and dihydrogen phosphate

被引:56
作者
Kim, Sook Kyung [1 ,2 ]
Seo, Dongwon [3 ]
Han, Su Jung [1 ,2 ]
Son, Guiyoup [3 ]
Lee, In-Ja [3 ]
Lee, Chongmok [1 ,2 ]
Lee, Kap Duk [3 ]
Yoon, Juyoung [1 ,2 ]
机构
[1] Ewha Womans Univ, Div Nano Sci BK21, Seoul 120750, South Korea
[2] Ewha Womans Univ, Dept Chem, Seoul 120750, South Korea
[3] Dongguk Univ, Dept Chem, Kyungju 780714, Kyungbuk, South Korea
关键词
D O I
10.1016/j.tet.2008.04.085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new acridine derivative bearing two imidazolium groups has been synthesized. This chemosensor displayed a large fluorescent quenching effect with pyrophosphate and a unique fluorescent enhancement with H(2)PO(4)(-). The strong (C-H)(+)center dot center dot center dot X(-) hydrogen bonding between the imidazolium moieties and anions is the key interaction for the recognition. The association constant of 1 with pyrophosphate was calculated as 4.9x10(7) M(-1). (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6402 / 6405
页数:4
相关论文
共 58 条
[1]   Synthesis and molecular recognition of pyrenophanes with polycationic or amphiphilic functionalities: Artificial plate-shaped cavitant incorporating arenes and nucleotides in water [J].
Abe, H ;
Mawatari, Y ;
Teraoka, H ;
Fujimoto, K ;
Inouye, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (02) :495-504
[2]   Dipyrrolyl quinoxalines with extended chromophores are efficient fluorimetric sensors for pyrophosphate [J].
Aldakov, D ;
Anzenbacher, P .
CHEMICAL COMMUNICATIONS, 2003, (12) :1394-1395
[3]   Sensing of aqueous phosphates by polymers with dual modes of signal transduction [J].
Aldakov, D ;
Anzenbacher, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) :4752-4753
[4]  
AOKI S, 2002, REV MOL BIOTECHNOL, V90, P129
[5]  
Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.3.CO
[6]  
2-G
[7]   Luminescent sensors and switches in the early 21st century [J].
Callan, JF ;
de Silva, AP ;
Magri, DC .
TETRAHEDRON, 2005, 61 (36) :8551-8588
[8]   Reactivity of the acridine ring: One-pot regioselective single and double bromomethylation of acridine and some derivatives [J].
Chiron, J ;
Galy, JP .
SYNLETT, 2003, (15) :2349-2350
[9]   A fluorescent pyrophosphate sensor via excimer formation in water [J].
Cho, HK ;
Lee, DH ;
Hong, JI .
CHEMICAL COMMUNICATIONS, 2005, (13) :1690-1692
[10]  
Conners K.A., 1987, BINDING CONSTANTS ME