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Chloride capture using a C–H hydrogen bonding cage

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Science  23 May 2019:
eaaw5145
DOI: 10.1126/science.aaw5145

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Abstract

Tight binding and high selectivity are hallmarks of biomolecular recognition. Achieving these behaviors with synthetic receptors has usually been associated with OH and NH hydrogen bonding. Contrary to this conventional wisdom, we designed a chloride-selective receptor in the form of a cryptand-like cage using only CH hydrogen bonding. Crystallography showed chloride stabilized by six short 2.7-Å hydrogen bonds originating from the cage’s six 1,2,3-triazoles. Atto-molar affinity (1017 M–1) was determined using liquid-liquid extractions of chloride from water into nonpolar dichloromethane solvents. Controls verified the additional role of triazoles in rigidifying the 3D structure to effect recognition affinity and selectivity: Cl > Br > NO3 > I. This cage shows anti-Hofmeister salt extraction and preliminary corrosion inhibition.

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