A zinc-salophen/bile-acid conjugate receptor solubilized by CTABr micelles binds phosphate in water.

Org Biomol Chem

Laboratory of Organic Chemistry, Department of Chemistry, P.O. Box 35, 40014, Jyväskylä, Finland.

Published: July 2013

Receptor 1, composed of two deoxycholic acid moieties appended to a Zn-salophen complex, was prepared, characterized and tested for anion binding by (1)H NMR and UV-vis spectroscopic techniques. While in polar DMSO, 1 is able to bind phosphate (K = ∼700 M(-1)), the addition of water severely diminishes the association. In a 1 : 9 water-DMSO mixture, the binding constant K is only ca. 20 M(-1). Notably, in an aqueous solution of CTABr micelles (CTABr 10 mM, cmc = ∼1 mM), the zinc-salophen conjugate 1, due to its two non-polar bile-acid moieties, becomes solubilized and, most importantly, it almost completely recovers its binding ability towards phosphate, displaying a remarkable affinity (K = ∼450 M(-1)) in water.

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http://dx.doi.org/10.1039/c3ob40724aDOI Listing

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