Thiourea-Functionalized Glycophane Macrocycles for Selective Recognition of Phthalate Isomers.

We report the synthesis of water-soluble glycophanes tailored for the selective recognition of related aromatic dicarboxylic acids─phthalate isomers─in both DMSO-d6 and highly competitive D2O. Key novel design aspects are the generation of distal thiourea hydrogen bonding donors by isothiocyanate-amino coupling of C2-symmetric aryl pseudodisaccharides or the stepwise elaboration of α,α'-d-trehalose scaffolds. NMR titrations revealed differentiated binding constants across host-guest pairs, including the water recognition of sodium terephthalate.