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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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Supplementary files

Article information


Submitted
15 May 2012
Accepted
27 Jun 2012
First published
28 Jun 2012

Org. Biomol. Chem., 2012,10, 6951-6959
Article type
Paper

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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