Hydrogen-bonding A(LS)2-type low-molecular-mass gelator and its thermotropic mesomorphic behavior

A unique cholesterol-based A(LS)2-type gelator, which is a hydrogen-bonding complex based on an ALS-type non-gelator molecule 3-cholesteryl 4-(trans-2-(4-pyridinyl)vinyl)phenyl succinate and a counterpart 3-cholesteryloxycarbonylpropanoic acid, shows strong gelation ability in alcohol and aromatic solvents. The formed gel has a high Tg at low gelation concentration, and its xerogel shows fibrillar microstructure revealed by scanning electron microscopy (SEM). FTIR confirms the existence of intermolecular hydrogen bond in the gelator, and X-ray diffraction (XRD) analysis reveals that the gelator possesses a folded conformation in gel and self-assembles into the fibrillar structure mainly by van der Waals interaction between cholesteryl moieties of the gelator. Further more, the thermotropic behavior of the xerogel is studied by differential scanning calorimetry (DSC) and polarized optical microscopy (POM), which shows typical optical textures of liquid crystals.

A hydrogen-bonding A(LS)2-type gelator shows fibrillar microstructure in xerogel (left) and fan-shaped texture in thermotropic mesophase (right).Figure optionsDownload as PowerPoint slide