Anion binding in aqueous media by a tetra-triazolium macrocycle(Article)

Organic and Biomolecular Chemistry

Journal Article

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 > 10 4 M -1). Quantum mechanics/molecular mechanics simulations corroborate the experimentally determined anion binding selectivity trends. © 2012 The Royal Society of Chemistry.

N.G.a White

V.b Félix

P.D.a Beer

Publication

Year of publication: 2012

Identifiers

ISSN: 14770520

Locators

DOI: 10.1039/c2ob25934f

Alternative Titles