Issue 1, 2012

Extending the family of heteroditopic calix[4]diquinone receptors for cooperative AND ion-pair recognition

Abstract

New heteroditopic calix[4]diquinone receptors with different anion binding units and calix[4]diquinone scaffolds have been synthesised. Ion-pair binding studies using UV/visible and 1H NMR spectroscopies reveal that receptors 1, 2 and 4 are cooperative AND ion-pair receptors, which display little affinity for ‘free’ ions but enhanced binding of the ion-pairs NaCl, NH4Cl and KCl. The more preorganised receptor 2 binds the ion-pairs more weakly than receptor 1. Varying the nature of the calix[4]diquinone scaffold appears to have little effect on ion-pair binding, although the calix[4]diquinone framework is more conformationally flexible than the tert-butylcalix[4]diquinone one and can be synthesised using the milder oxidant chlorine dioxide.

Graphical abstract: Extending the family of heteroditopic calix[4]diquinone receptors for cooperative AND ion-pair recognition

Supplementary files

Article information

Article type
Paper
Submitted
12 Aug 2011
Accepted
13 Sep 2011
First published
28 Oct 2011

New J. Chem., 2012,36, 102-112

Extending the family of heteroditopic calix[4]diquinone receptors for cooperative AND ion-pair recognition

A. J. McConnell, C. J. Serpell and P. D. Beer, New J. Chem., 2012, 36, 102 DOI: 10.1039/C1NJ20708C

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