“Off-on” aggregation-based fluorescent sensor for the detection of chloride in water?

Organic & Biomolecular Chemistry Pub Date: 2015-02-27 DOI: 10.1039/C4OB02409E

Abstract

Receptors selective for anions in aqueous media are a crucial component in the detection of anions for biological and environmental applications. Recent sensor designs have taken advantage of systems known to aggregate in solution, eliciting a fluorescent response. Herein, we demonstrate a chloride-selective fluorescent response of receptor 1+, based on our well-established class of 2,6-bis(2-anilinoethynyl)pyridine bisureas. The fluorescence intensity ratio of 1+·Cl?> aggregates in water is four times larger than the next most fluorescent anion complex, 1+·ClO4?>. In addition, 1H NMR spectroscopic titrations demonstrate 1+ binds chloride more strongly than other biologically relevant anions in solutions of both DMSO-d6 and 50/50 DMSO-d6/MeCN-d3.

Graphical abstract: “Off-on” aggregation-based fluorescent sensor for the detection of chloride in water
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