Foldamers are an important class of abiotic macromolecules,w ith potential therapeutic applications in the disruption of protein-protein interactions.T he majority adopt as ingle conformational motif such as ah elix. Ac lass of foldamer is now introduced where the choice of heterocycle within each monomer,c oupled with as trong conformationdetermining dipole repulsion effect, allows both helical and extended conformations to be selected. Combining these monomers into hetero-oligomers enables highly controlled exploration of conformational space and projection of sidechains along multiple vectors.T he foldamers were rapidly constructed via an iterative deprotection-cross-coupling sequence,a nd their solid-and solution-phase conformations were analysed by X-rayc rystallography and NMR and CD spectroscopy. These molecules may find applications in protein surface recognition where the interface does not involve canonical peptide secondary structures.