Aromatic Pentaamide Macrocycles as High‐Affinity Sulfate Binders and Efficient Transporters

Abstract

Abstract The binding and transport of the highly hydrophilic sulfate ion pose a significant challenge. Receptors capable of both strong sulfate binding and efficient transport are rare. Macrocycles c5 , featuring a constrained aromatic amide backbone that convergently locks multiple amide NH and phenyl NH donors, along with five large amide dipoles, create a preorganized, electropositive cavity that binds sulfate in a 1:1 stoichiometry, with affinities ( K a ’s) from 10 8 to 10 13 M −1 in solvents of low to high polarity. The water‐soluble c5c binds sulfate, forming a 4:1 complex in aqueous solution. Macrocycles c5a and c5b with hydrophobic sidechains serve as carriers that mediate efficient sulfate transport across both a bulk chloroform phase and lipid bilayers. With their synthetic tunability, macrocycles c5 can be tailored to media of different properties, yielding effective sulfate binders and carriers with broad applicability.