Substituent‐Driven Anion‐Binding Selectivity in Aliphatic Chain‐Substituted 1,2‐Phenylene Urea Macrocycles and Optimized Synthetic Methodology

Decorating the periphery of the 1,2-phenylene urea macrocycle with butoxy groups leads to a disruption of the ability of the compound to form self-assembled channels, which is typical for this class of receptors. For this reason, the molecule adopts a selectivity for dihydrogen phosphate. In addition, a simplified synthetic procedure is presented.

Abstract

1,2-Phenylene tetraurea macrocycles recently attracted attention as self-assembled channel-making compounds with high selectivity to chlorides. Here, we report on the introduction of aliphatic chains in the periphery of the 1,2-phenylene tetraurea macrocycle, which led to deterioration in the ability of the macrocycle to form channels and to a reversal of anion binding preferences in favour of dihydrogen phosphate. In addition, we have developed a new method of synthesis of 1,2-phenylene tetraurea macrocycle, using a direct click of two diamino ureido derivatives by triphosgene in the presence of chloride template. This approach saves time and eliminates demanding isolation of the non-cyclic tetrameric intermediates.

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