Self-Assembly of Alkylamido Isophthalic Acids toward the Design of a Supergelator: Phase-Selective Gelation and Dye Adsorption.

Abstract

A new series of 5-alkylamido isophthalic acid (ISA) derivatives with varying single and twin alkyl chain lengths were designed and synthesized as potential supramolecular organogelators. 5-alkylamido ISAs with linear or branched alkyl tail-groups of different lengths were effective gelators for low polarity solvents. In particular, among the presented series, a derivative with a branched, 24 carbon atom tail-group behaves as a “supergelator” with up to twenty organic solvents forming gels that are highly stable over time. The gelation behavior was analyzed using Hansen solubility parameters, and the thermal stability and viscoelastic properties of select gels were characterized. Microscopy, spectroscopy, powder X-ray diffraction, and computer modeling studies were consistent with a hierarchical self-assembly process involving the formation of cyclic H-bonded hexamers via the ISA carboxylic acid groups, which stack into elementary fibers stabilized by H-bonding of the amide linker groups and π–π stacking of the aromatic groups. These new nanomaterials exhibited potential for the phase-selective gelation of oil from oil–water mixtures and dye uptake from contaminated water. The work expands upon the design and synthesis of supramolecular self-assembled nanomaterials and their application in water purification/remediation.