A variety of foldamers that adopt well-defined secondary structures have been developed to mimic the hierarchical structure found in many biomacromolecules. The ortho-phenylenes are among the simplest aromatic foldamers, folding into helices driven by (offset) arene-arene stacking interactions. o-Phenylenes offer an attractive combination of properties: simple conformational behavior which is slow on the NMR time scale around room temperature and a predictable relationship of their NMR spectra to their geometries, which makes these systems well-suited for the study of folding in solution. Functional geometry changes are broadly found in proteins, for example in cell signaling or allosteric regulation. Given that proteins serve as inspiration for the field, it is not surprising that efforts have been made to study how events (e.g., binding, photochemistry) at one end of a foldamer can be communicated to and then detected at the other. Our group has recently shown that conformational control in o-phenylene foldamers can be achieved by attaching chiral amide groups to their termini. Here, we discuss the synthesis of ortho-phenylenes with a reporter (chiral amide) group at one end and a binding site (aldehyde group) at the other. We investigate long-range structural communication by binding a chiral guest molecule at the binding site using a combination of NMR spectroscopy, CD spectroscopy, and computational analysis.

Long-range structural communication in ortho-phenylenes

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