Organogels Based on 1<i>H</i>-Imidazolecarboxamide Amphiphiles

Abstract

We prepared 1H-imidazolecarboxamide amphiphiles as potential organogelators. Compounds A1-A3, in which an imidazole head was connected to a hydrophobic trialkyloxyphenyl group, showed an ability to gelate nonpolar solvents, including alkanes. The dry gels obtained from compounds A1-A3 had columnar hexagonal structures. Polycatenar 1H-imidazolecarboxamide amphiphile B2, consisting of a 1H-imidazole head connected through a benzene ring to a tridecyloxyphenyl tail, formed an organogel in DMSO. In a concentrated THF solution (30 wt %), compound B2 exhibited a lyotropic liquid-crystalline phase with a columnar hexagonal structure. X-ray diffraction (XRD) results suggested a molecular arrangement consisting of a disk, via hydrogen bonding between successive imidazole moieties, and an assembly of columnar structures.