Document Type

Article

Rights

This item is available under a Creative Commons License for non-commercial use only

Disciplines

1.4 CHEMICAL SCIENCES

Publication Details

Journal of the American Chemical Society (JACS)

Abstract

A neutral 2-site chloride selective compound has been developed (3), based on a 1,3- alternate tetrasubstituted calix[4]arene providing a preorganised supramolecular scaffold. The resultant supramolecular cavity is amongst 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 signalling 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 amongst a wide variety of anions tested. 3 has an association constant of 2.4×104M-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 8×10-6M with chloride in acetonitrile-chloroform (95:5 v/v). A dynamic fluorescence study revealed a response time ofproduct.

DOI

https://doi.org10.1021/ja061917m

Funder

Enterprise Ireland, grant code SC/2002/161, Science Foundation Ireland for support under the Adaptive Information Cluster award (SFI03/IN3/1361) and the Environmental Protection Agency, Ireland, funding code EPA2004-RS-AIC-M4.

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