An ion pair receptor showing remarkable enhancement of anion-binding strengths in the presence of alkali metal cations

Kyu-Sung Jeong, Min Kyung Chae, Jung-In Lee, Nam-Kyun Kim

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An ion pair receptor was prepared by coupling of a diazacrown ether and a rigid biindole scaffold bearing hydrogen bond donors of two indole NHs. The former serves as the cation-binding site and the latter functions as the anion-binding site. The anion-binding affinities to the receptor, determined by 1H NMR titration experiments in 10% (v/v) DMSO-d6/CD3CN at 24 ± 1 °C, have been greatly improved when an alkali metal cation binds to the adjacent diazacrown ether. For example, the association constant between chloride and receptor alone is 7 M−1, but the magnitudes increase into 120 M−1, 14,000 M−1, and 6200 M−1 in the presence of lithium, sodium, and potassium ions, respectively. The enhanced binding affinities must be attributed to electrostatic interactions by possibly forming contact ion pairs.
Original languageEnglish
Pages (from-to)6624-6627
Number of pages4
JournalTetrahedron Letters
Issue number38
Publication statusPublished - 2007 Sep 17


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