Foldamers, artificial oligomers that fold by analogy with biomacromolecules, have been of significant interest for decades. Many aromatic foldamers have been developed that fold into (chiral) helical secondary structures. Unlike nature's building blocks, however, aromatic repeat units are typically not chiral. Consequently, simple aromatic foldamers will exist as (dynamic) racemates. This is an issue for any systems dependent on interactions with chiral species, including homoassembly of the foldamers themselves. Controlling helical twist sense is thus necessary to achieve full control over structure. This is typically done by attaching groups containing chirality centers at the side chains or termini of the oligomer, with the point chirality of these groups communicated to the helix via intramolecular interactions. o-Phenylenes are simple class of aromatic foldamers. An example of a perfectly folded o-phenylene heptamer, oP , is shown in Figure . The helix has three repeat units per turn, stabilizing the folded conformer through arene-arene interactions between every third repeat unit. o-Phenylenes are conformationally dynamic and their geometries can be studied in detail by NMR spectroscopy, making them well-suited to studying problems in molecular folding. In recent work, we have demonstrated the coassembly of o-phenylenes and rod-shaped linkers into macrocycles comprising multiple foldamer subunits as simple examples of folded systems with higher-order structure. However, there is essentially no stereocontrol in these systems: the product macrocycles comprise both twist senses of the foldamers (M and P) in statistical ratios. As a result, the products are complex racemic mixtures of multiple diastereomers. Functional systems based on the macrocycles require that the handedness of the o-phenylenes be controlled.