Self-assembly of a Chiral Amphiphilic Macrocyclic Diacetylene
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Creation of chiral superstructures through self-assembly of small organic chiral molecules has gained significant attention. Owing to the intrinsic pore generation, molecular stacking of macrocyclic compounds has been actively investigated. Macrocyclic diacetylenes (MCDAs) are unique since self-assembly followed by UV induced polymerization can lead to the formation of rigid nanotubular structures. Amphiphilic MCDAs are structurally intriguing and resulted in the generation of 2D nanosheets with tubular channels and striated hollow nanotubes. Herein we present new supramolecular structures derived from a chiral amphiphilic MCDA. A enantiomerically pure phenylalanine-substituted oligoethylene glycol-containing MCDAs, MCDA-L-Phe-OEG and MCDA-D-Phe-OEG were prepared. The water-compatible chiral MCDAs resulted in the formation of helical fibers under self-assembly conditions in aqueous solution. Interestingly, UV irradiation to the helical fiber solution afforded generation of polydiacetylene, which was confirmed by spectroscopically.