Anion binding in aqueous media by a tetra-triazolium macrocycle

authors	White, NG; Carvalho, S; Felix, V; Beer, PD
nationality	International
journal	ORGANIC & BIOMOLECULAR CHEMISTRY
keywords	6-AMINOPICOLINIC ACID SUBUNITS; HYDROGEN-BONDS; ARYL-TRIAZOLE; SELECTIVE RECOGNITION; COMPUTER-PROGRAM; TERMINAL ALKYNES; RECEPTOR; CHLORIDE; COMPLEXATION; IONS
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 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.
publisher	ROYAL SOC CHEMISTRY
issn	1477-0520
year published	2012
volume	10
issue	34
beginning page	6951
ending page	6959
digital object identifier (doi)	10.1039/c2ob25934f
web of science category	Chemistry, Organic
subject category	Chemistry
unique article identifier	WOS:000307306500017