Synthesis of 1,(3S)-Bis[N-p-aryl)-carbamoyloxy]butane as new low molecular weight organogelators

Low molecular weight organic compounds (LMWOs) have the potential to form gels at low concentrations (below 5 wt%) in organic solvents. These compounds form supramolecular networks with weak, non-covalent bonds such as hydrogen bonds, van der Waals forces and π-π interactions. These networks lead to the components forming fibrous, tubular or helical structures and the entrapment of solvent molecules. Structural groups such as aromaticity, hydrogen bonds and aliphatic chains play an important role in gel formation. Moreover, self-assembly processes are influenced by the spatial arrangement of the functional groups of compounds, which creates differences in the gelation abilities of chiral compounds. By influencing molecular stacking, chiral centers can determine whether a compound will function as an organogelator or not. In this project, chiral p-alkyl and p-alkoxy substituted 1,(3S)-Bis-[N-(p-aryl)-carbamoyloxy]butane derivatives were synthesized by reacting p-aryl isocyanates with (S)-(+)-1,3-Butanediol or by the reaction of p-substituted benzoic acid with diphenylphosphoryl azide. After purification and characterization of the compounds, their organogelization abilities in achiral solvents were investigated by test tube inversion method.