Chloride selective calix[4]arene optical sensor combining urea functionality with pyrene excimer transduction

被引：236

作者：

Schazmann, Benjamin ^{[1
]}

Alhashimy, Nameer ^{[1
]}

Diamond, Dermot ^{[1
]}

机构：

[1] Dublin City Univ, Adapt Sensors Grp, Natl Ctr Sensor Res, Sch Chem Sci, Dublin 9, Ireland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 26期

关键词：

D O I：

10.1021/ja061917m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A neutral 2-site chloride selective compound has been developed (3), based on a 1,3-alternate tetrasubstituted calix[4] arene providing a preorganized supramolecular scaffold. The resultant supramolecular cavity is among the first to combine urea functional groups bridged with single methylene spacers to pyrene moieties. It combines a naturally and synthetically proven H-bonding system with the elegant ratiometric fluorescent signaling properties of an intramolecular pyrene excimer system, triggered by conformational changes upon anion coordination. The excimer emission of 3 is quenched, with a simultaneous rise in the monomer emission solely by the chloride anion among a wide variety of anions tested. 3 has an association constant of 2.4 x 10(4) M-1 with chloride. The suitability and advantages of ratiometric optical sensor compounds like 3 for use in practical sensor devices is discussed. 3 has an LOD of 8 x 10(-6) M with chloride in acetonitrile-chloroform (95:5 v/ v). A dynamic fluorescence study revealed a response time of < 3 s. A recently developed and simple HPLC-based purification method complimented conventional organic work up methods to yield pure product.

引用

页码：8607 / 8614

页数：8

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