Homochiral versus Heterochiral Dimeric Helical Foldamer Bundles: Chlorinated‐Solvent‐Dependent Self‐Sorting.

Aromatic oligoamide sequences programmed to fold into stable helical conformations were designed to display a linear array of hydrogen‐bond donors and acceptors at their surface. Sequences were prepared by solid‐phase synthesis. Solution 1H NMR spectroscopic studies and solid‐state crystallographic structures demonstrated the formation of stable hydrogen‐bond‐mediated dimeric helix bundles that could be either heterochiral (with a P and an M helix) or homochiral (with two P or two M helices). Formation of the hetero‐ or homochiral dimers could be driven quantitatively using different chlorinated solvents—exemplifying a remarkable case of either social or narcissistic chiral self‐sorting or upon imposing absolute handedness to the helices to forbid PM species. [ABSTRACT FROM AUTHOR]