Expedient Decagram-Scale Synthesis of Robust Organic Cages That Bind Sulfate Strongly and Selectively in Water

Abstract

Selective anion recognition remains a key challenge in supramolecular chemistry: only a very small number of systems that can function in water are known, and these nearly always preferentially bind hydrophobic anions. In this work, we report three robust hexa-cationic cages that can be prepared on scales up to 14 g in two simple and high-yielding steps from commercially available materials. One of these cages displays unusually strong sulfate binding in water (Ka = 12,000 M-1), and demonstrates high selectivity for this anion over H2PO4-/HPO42- in DMSO/buffer mixtures. These results demonstrate that relatively large, three-dimensional supramolecular hosts can be prepared in high yields and on large scales, and can be highly potent receptors.