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Schazmann B, Alhashimy N, Diamond D. Chloride selective calix[4]arene optical sensor combining urea functionality with pyrene excimer transduction. J Am Chem Soc. 2006;128(26):8607-14doi: 10.1021/ja061917m.
Schazmann, B., Alhashimy, N., & Diamond, D. (2006). Chloride selective calix[4]arene optical sensor combining urea functionality with pyrene excimer transduction. Journal of the American Chemical Society, 128(26), 8607-14. https://doi.org/10.1021/ja061917m
Schazmann, Benjamin, et al. "Chloride selective calix[4]arene optical sensor combining urea functionality with pyrene excimer transduction." Journal of the American Chemical Society vol. 128,26 (2006): 8607-14. doi: https://doi.org/10.1021/ja061917m
Schazmann B, Alhashimy N, Diamond D. Chloride selective calix[4]arene optical sensor combining urea functionality with pyrene excimer transduction. J Am Chem Soc. 2006 Jul 05;128(26):8607-14. doi: 10.1021/ja061917m. PMID: 16802827.
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J Am Chem Soc. 2006 Jul 05;128(26):8607-14. doi: 10.1021/ja061917m.

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

Journal of the American Chemical Society

Benjamin Schazmann, Nameer Alhashimy, Dermot Diamond

Affiliations

  1. Adaptive Sensors Group, National Centre for Sensor Research, School of Chemical Sciences, Dublin City University, Dublin 9, Ireland.

PMID: 16802827 DOI: 10.1021/ja061917m

Abstract

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.

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