Novel fluorescein appended calix[4]arenes for preferential recognition of Cu2+ ions

被引:25
作者
Chawla, Har Mohindra [1 ]
Shukla, Richa [1 ]
Pandey, Shubha [1 ]
机构
[1] Indian Inst Technol Delhi, Dept Chem, New Delhi 110016, India
关键词
Calixarenes; Fluorescence; Copper ion; Recognition; Chemosensor; SELECTIVE FLUORESCENT; LIVING CELLS; METAL-IONS; CHEMOSENSORS; SENSOR; CU(II); DERIVATIVES; RECEPTORS; COPPER; WATER;
D O I
10.1016/j.tetlet.2013.02.017
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel calix[4]arene derivatives with fluorescein appendages (7 and 8) were synthesized for application in preferential recognition of Cu2+ ions over other metal ions through enhancement of fluorescence intensity with a detection limit up to nanomolar level in acetonitrile. A profound color change from colorless to yellow in acetonitrile and colorless to purple in aqueous medium indicates specific copper ion recognition plausibly due to selective ring opening of fluorescein spirolactam functionality. The synthesized receptor shows high selectivity and reversibility required for developing efficient chemosensors for Cu2+. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2063 / 2066
页数:4
相关论文
共 57 条
[1]   Fluorescein-based fluorescent and colorimetric chemosensors for copper in aqueous media [J].
Abebe, Fasil A. ;
Sinn, Ekkehard .
TETRAHEDRON LETTERS, 2011, 52 (41) :5234-5237
[2]  
[Anonymous], 2000, ENCY ANAL CHEM THEOR
[3]   Synthesis and solution structure analysis of a bispyrenyl bishydroxamate calix[4]arene-based receptor, a fluorescent chemosensor for Cu2+and Ni2+ metal ions [J].
Bodenant, B ;
Weil, T ;
Businelli-Pourcel, M ;
Fages, F ;
Barbe, B ;
Pianet, I ;
Laguerre, M .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) :7034-7039
[4]   Novel water-soluble β-cyclodextrin-calix[4]arene couples as fluorescent sensor molecules for the detection of neutral analytes [J].
Bügler, J ;
Engbersen, JFJ ;
Reinhoudt, DN .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) :5339-5344
[5]   Convenient direct synthesis of bisformylated calix[4]arenes via ipso substitution [J].
Chawla, H. M. ;
Pant, N. ;
Srivastava, Bindu ;
Upreti, Shailesh .
ORGANIC LETTERS, 2006, 8 (11) :2237-2240
[6]   A new class of functionalized calix[4]arenes as neutral receptors for colorimetric detection of fluoride ions [J].
Chawla, Har Mohindra ;
Shrivastava, Rahul ;
Sahu, Satya Narayan .
NEW JOURNAL OF CHEMISTRY, 2008, 32 (11) :1999-2005
[7]   Fluorescent Chemosensors Based on Spiroring-Opening of Xanthenes and Related Derivatives [J].
Chen, Xiaoqiang ;
Pradhan, Tuhin ;
Wang, Fang ;
Kim, Jong Seung ;
Yoon, Juyoung .
CHEMICAL REVIEWS, 2012, 112 (03) :1910-1956
[8]   New fluorescent and colorimetric chemosensors bearing rhodamine and binaphthyl groups for the detection of Cu2+ [J].
Chen, Xiaoqiang ;
Jou, Min Jung ;
Lee, Hanyoung ;
Kou, Songzi ;
Lim, Jeesun ;
Nam, Seong-Won ;
Park, Sungsu ;
Kim, Kwan-Mook ;
Yoon, Juyoung .
SENSORS AND ACTUATORS B-CHEMICAL, 2009, 137 (02) :597-602
[9]   A selective fluorescence-on reaction of spiro form fluorescein hydrazide with Cu(II) [J].
Chen, Xinqi ;
Ma, Huimin .
ANALYTICA CHIMICA ACTA, 2006, 575 (02) :217-222
[10]   Selective Perborate Signaling by Deprotection of Fluorescein and Resorufin Acetates [J].
Choi, Myung Gil ;
Cha, Sunyoung ;
Park, Ji Eun ;
Lee, Haekyung ;
Jeon, Hye Lim ;
Chang, Suk-Kyu .
ORGANIC LETTERS, 2010, 12 (07) :1468-1471