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Issue 12, 2007
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Anion recognition and anion-mediated self-assembly with thiourea-functionalised fused [3]polynorbornyl frameworks

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Abstract

Three conformationally preorganised host molecules based on the [3]polynorbornyl framework and incorporating di-urea receptors were synthesised and their interaction with a series of anions investigated by 1H NMR spectroscopy. A high affinity of each host molecule for dihydrogenphosphate (H2PO4) and dihydrogenpyrophosphate (H2P2O72−) was identified. In addition to binding to the urea receptors of the host molecules, evidence for an interaction involving the non-polar C–H groups within the binding cavity of the framework and guest anions was also discovered. Furthermore, an unusual 2 : 1 host-to-anion stoichiometry was indicated when binding H2P2O72−, and a model for the anion-mediated self-assembly of this complex species is proposed.

Graphical abstract: Anion recognition and anion-mediated self-assembly with thiourea-functionalised fused [3]polynorbornyl frameworks

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Publication details

The article was received on 02 Mar 2007, accepted on 24 Apr 2007 and first published on 14 May 2007


Article type: Paper
DOI: 10.1039/B703208K
Citation: Org. Biomol. Chem., 2007,5, 1894-1902
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    Anion recognition and anion-mediated self-assembly with thiourea-functionalised fused [3]polynorbornyl frameworks

    F. M. Pfeffer, P. E. Kruger and T. Gunnlaugsson, Org. Biomol. Chem., 2007, 5, 1894
    DOI: 10.1039/B703208K

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