Supramolecular design of benzene-1,3,5-tricarboxamide with hydrophobic alkyl side chains toward long-range liquid crystalline properties

Abstract

Herein we report the first approach of benzene-1,3,5-tricarboxamides (BTAs) with long-range liquid crystalline properties by utilizing hydrophobic alkyl side chains at the amide functional group. These compounds were successfully prepared in high yields by reacting 1,3,5-benzenetricarbonyl trichloride with series of aliphatic linear alkyl amines as the side chains. By increasing the length of hydrocarbon chains at the amino, thermograms of BTAs showed the formation of mesophase rangesbetween 21.8- 196.3, 41.9 - 212.4, 57.9 - 203.7, 76.1 - 207.7 and 80.5 - 200.1 degrees for decylamine, dodecylamine, tetradecylamine, hexadecylamineand octadecylamine, respectively. Such liquid crystalline properties indicate the formation of self-assembly through supramolecular interactions with a lamellar structure. In particular, benzene tricarboxamide with short alkyl chains will reduce the Van der Waals interactions to give room temperature range of mesophase structure.