Directional Threading and Sliding of a Dissymmetrical Foldamer Helix on Dissymmetrical Axles

We have investigated the self‐assembly of a dissymmetrical aromatic oligoamide helix on linear amido‐carbamate alkyl and PEG chains. A dissymmetrical sequence bearing two differentiated ends is able to wind itself around dissymmetrical dumbbell rod‐like guest molecules. Structural and thermodynamic investigations allowed us to decipher the specific mode of binding of the helix to the amide and carbamate groups of the rod. In parallel kinetic studies of threading and sliding of the helix along linear axles were monitored by 1H NMR. Results show that threading of a dissymmetrical host can be kinetically biased by the nature of the guest terminus allowing for a preferential orientation of sliding of the helix. This study thus further demonstrates the usefulness of foldaxanes to combine designed molecular recognition patterns with fine control of self‐assembly kinetics in order to orchestrate supramolecular events.

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