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Issue 34, 2012
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Anion binding in aqueous media by a tetra-triazolium macrocycle

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Abstract

Three tetra-triazole macrocycles were synthesized in good yields by the copper(I)-catalysed cycloaddition of bis-triazole azides and bis-alkynes. One of these was alkylated to give a cyclic tetra-triazolium receptor, which complexes anions strongly in competitive DMSOwater mixtures. In 1 : 1 DMSOwater, the tetracationic receptor exhibits a preference for the larger halides, bromide and iodide, with all halides associating more strongly than the oxoanion, acetate. The sulfate dianion is complexed far more strongly than any of the monobasic anions (Ka > 104 M−1). Quantum mechanics/molecular mechanics simulations corroborate the experimentally determined anion binding selectivity trends.

Graphical abstract: Anion binding in aqueous media by a tetra-triazolium macrocycle

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Publication details

The article was received on 15 May 2012, accepted on 27 Jun 2012 and first published on 28 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25934F
Citation: Org. Biomol. Chem., 2012,10, 6951-6959
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    Anion binding in aqueous media by a tetra-triazolium macrocycle

    N. G. White, S. Carvalho, V. Félix and P. D. Beer, Org. Biomol. Chem., 2012, 10, 6951
    DOI: 10.1039/C2OB25934F

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