Anion binding in aqueous media by a tetra-triazolium macrocycle

Nicholas G. White; Sílvia Carvalho; Vítor Félix; Paul D. Beer

doi:10.1039/C2OB25934F

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Organic & Biomolecular Chemistry

Issue 34, 2012

The international home of synthetic, physical and biomolecular organic chemistry.

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Paper

Anion binding in aqueous media by a tetra-triazolium macrocycle

Nicholas G. White,^a Sílvia Carvalho,^b Vítor Félix^b and Paul D. Beer*^a

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Chemistry Research Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, United Kingdom
E-mail: paul.beer@chem.ox.ac.uk ;
Fax: +44 (0)1865 272690 ;
Tel: +44 (0)1865 285142

Departamento de Química, CICECO and Secção Autónoma de Ciências da Saúde, Universidade de Aveiro, 3810-193 Aveiro, Portugal

Org. Biomol. Chem., 2012,10, 6951-6959

DOI: 10.1039/C2OB25934F
Received 15 May 2012, Accepted 27 Jun 2012
First published online 28 Jun 2012

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Abstract
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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 DMSO–water mixtures. In 1:1 DMSO–water, 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 (K_a > 10⁴ M⁻¹). Quantum mechanics/molecular mechanics simulations corroborate the experimentally determined anion binding selectivity trends.