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Org Lett. 2013 Nov 15;15(22):5638-41. doi: 10.1021/ol402500q. Epub 2013 Oct 29.

Colorimetric and luminescent sensors for chloride: hydrogen bonding vs deprotonation.

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  • 1School of Chemistry (F11), The University of Sydney , NSW 2006, Australia.


The synthesis and photophysical properties of four squaramide based fluorescent anion sensors (1-4) are described. These luminescent compounds showed selectivity for Cl(-) over various other anions with concomitant changes in both their UV/visible and fluorescence properties upon Cl(-) addition, attributed to initial H-bonding followed by NH deprotonation in the presence of excess Cl(-), signaled by a color change. The nature of the electron withdrawing aryl substituents is directly related to the H-bonding ability/acidity of the squaramide protons and can be used to tune the deprotonation behavior.

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