Homochiral versus Heterochiral Dimeric Helical Foldamer Bundles: Chlorinated‐Solvent‐Dependent Self‐Sorting
Friedericke S. Menke, Barbara Wicher, Victor Maurizot, Ivan Huc
Abstract
Abstract 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 1 H 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.