Supramolecular self-assembly of two-component systems comprising aromatic amides/Schiff base and tartaric acid

Abstract

The gelating properties and thermotropic behaviors of stoichiometric mixtures of aromatic amides 1, 2, and the aromatic Schiff base 3 with tartaric acid (TA) were investigated. Among the three gelators, 2-TA exhibited superior gelating ability. Mixture 2-TA exhibits a smectic B phase and an unidentified smectic mesophase during both heating and cooling runs. The results of Fourier transform infrared spectroscopy and X-ray diffraction revealed the existence of hydrogen bonding and p-p interactions in 2-TA systems, which are likely to be the dominant driving forces for the supramolecular self-assembly. Additionally, it was established that all of the studied gel self-assemblies and mesophases possess a lamellar structure. The anion response ability of the tetrahydrofuran gel of 2-TA was evaluated and it was found that it was responsive to the stimuli of F⁻, Cl⁻, Br⁻, I⁻, AcO⁻.

Graphical abstract

Keywords

supramolecular self-assembly / organogel / liquid crystal / tartaric acid / hydrogen bond

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