Self-assembled Polydiacetylene Nanoribbons for Semi-heterogeneous and Enantioselective Organocatalysis of Aldol Reactions in Water

We report the synthesis, characterization, and supra-molecular assembly of novel diacetylene amphiphilic units bearing a chiral proline-derived head group. In water, these amphiphiles self-assemble into twisted ribbons that are photo-polymerized to afford stable nanostructures. The nanoribbons were valorized in the semi-heterogeneous and enantioselective catalysis of aldol reactions in water. The system is active on a variety of substrates, operates under sustainable conditions (room temperature, air atmosphere, low catalyst loading), and provides access to the target compounds with high enantiomeric excess. Moreover, the organocatalyst can be recycled over several runs with no loss in activity.