Preparation and self-assembly study of amphiphilic and bispolar diacetylene-containing glycolipids.

Diacetylene-containing glycolipids are a unique class of compounds that are able to self-assemble and form ordered supramolecular structures. Polymerizable diacetylene glycolipids that can function as low molecular weight gelators are particularly interesting molecules which can lead to stimuli-responsive smart materials. To discover efficient organogelators with built-in functionality that may be useful in sensing local environmental changes, we have synthesized a series of novel diacetylene-containing amide and urea derivatives using D-glucosamine as the starting material. Both amphiphilic and dipolar glycolipids were synthesized, and these compounds are effective gelators for several organic solvents and aqueous solutions. The resulting gels can be cross-linked under 6 W UV light to produce blue or purple polydiacetylene gels. The cross-linked gels obtained from urea derivatives are generally dark blue and exhibit blue to red color transitions upon heating. Compared to the urea derivatives, the analogous diacetylene amides produced blue to deep purple polymerized gels, depending on the structures of the gelators. The morphologies of the gels were characterized by optical microscopy and scanning electron microscopy. Typically, self-assembled fibrous networks were observed. The synthesis and characterization of these polymerizable gelators and their UV-vis absorption upon polymerization are reported.