A set of o-phenylene heptamers substituted with chiral imides has been synthesized and studied by NMR and CD spectroscopies. In the absence of further substitution, chiral induction from the substituents to the o-phenylene is limited because of ineffective interactions between the groups about the chirality center and the helix. Strategically functionalizing the o-phenylene backbone with simple substituents that can interact with the imides gives both inversion of the sense of chiral induction and substantial increases in de, up to (69 ± 10)% in the best case. DFT models suggest that this is primarily a steric effect.