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J Am Chem Soc. 2010 Sep 22;132(37):12838-40. doi: 10.1021/ja105793c.

Flipping the switch on chloride concentrations with a light-active foldamer.

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  • 1Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, USA.

Abstract

Here we demonstrate a bioinspired system where light stimulus is used to trigger the wavelength-dependent release and then reuptake of chloride ions in nonaqueous solutions. A chiral aryl-triazole foldamer with two azobenzene end groups has been synthesized to define a folded binding pocket for chloride ions that unfolds with UV light to liberate the chloride. The trans-dominated helical foldamer becomes less stable upon photoisomerization to the cis forms. Simultaneously, the observed binding affinity shows an ∼10-fold reduction from K = 3000 M(-1) (MeCN, 298 K). Control of chloride levels using light is demonstrated by switching the conductivity of an electrolyte solution up and down.

PMID:
20799723
DOI:
10.1021/ja105793c
[PubMed - indexed for MEDLINE]
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