Foldamers are non-biological oligomers that fold to generate conformationally ordered structures in solution. They mimic the behavior of important biomolecules with diverse functional behaviors including molecular recognition, self-assembly, catalysis, biological activity, and interesting electrical properties. Over the decades, a wide range of foldamers has been developed. The ortho-phenylenes are among the simplest aromatic foldamers. Recent studies have shown that they fold into helices in solution and the solid-state and their conformational changes are slow enough to be observed on an NMR time scale around room temperature. Our group has recently shown that biased helical twist sense in these ortho-phenylene foldamers can be induced by attaching chiral imines to their termini. Here, we discuss the synthesis of ortho-phenylenes functionalized with chiral amide groups at their terminal positions and investigate the chiral induction using a combination of NMR spectroscopy and CD spectroscopy.

Chiral induction in ortho-phenylenes terminally functionalized with amides

ACS Spring Meeting 2021

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