Oligo(5-amino-N-acylanthranilic acids): Amide Bond Formation without Coupling Reagent and Folding upon Binding Anions

Oligomers of 5-amino-N-acylanthranilic acid, previously unknown aromatic oligoamides that cannot be obtained with known amide coupling methods, are synthesized based on a new, highly efficient amide-bond formation strategy that takes advantage of the ring-opening of benzoxazinone derivatives. These oligoamides offer multiple backbone NH groups as H-bond donors which, in the presence of iodide or chloride ion, are convergently arranged and H-bonded, which enforces a folded, crescent conformation. These aromatic oligoamides provide a versatile platform based on which anion-dependent foldamers, or anion binders with tunable affinity and specificity, are being constructed.