Crescent Oligoamides: From Acyclic “Macrocycles” to Folding Nanotubes

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Abstract
Oligoarylamides whose backbones are rigidified by intramolecular hydrogen bonds (H-bonds) are found to adopt well-defined conformations in both solution and solid state. Depending on the length of their backbones, these folding oligoamides are crescents, broken macrocycles, or helices. A large (≈10 Å) interior cavity is associated with the “macrocycles” and helices. The folded conformations are independent of chain length and are found in both nonpolar and polar solvents. This strategy is being extended to the construction of folding acyclic “macrocycles” and nanotubes with larger tubular cavities.