Self-assembled nanohelix from a bolaamphiphilic diacetylene via hydrogelation and selective responsiveness towards amino acids and nucleobases.

A bolaamphiphile with diacteylene mesogen unit and l-glutamic acid as the terminal group was newly designed and its self-assembly was investigated. The compound formed hydrogels with water upon heating and cooling. The as-formed gel could be switched to a dispersion upon mechanical shaking. Both the gel and the water dispersion undergo polymerization upon UV irradiation. However, the gel turned to blue and then purple red color, while the dispersion turned red directly. Using AFM and SEM observations, it was found that nanohelix was formed in the as-prepared gel and polymerized blue gels, while nanobelt was formed from the water dispersion. The blue nanohelix was stable but showed selective response to certain amino acids and nucleobases. It was found that the blue gel underwent shrinkage when reacting with charged amino acids such as Glu, Asp, Lys, Arg and His. In the shrunk gel, the solution phase further turned pink in the case of His and Arg. In addition, the blue gel showed also shrinkage and color change when reacting with cytosine.