A novel tetrathiafulvalene-based organogelator with multi-stimuli responsiveness and dye adsorption

To create multi-stimulus responsive organogels, a novel low-molecular-weight organic gelator (LMMG) 1 was synthesized by linking two photoresponsive azobenzene groups with two hydrophobic chains containing amide functionalities to a central electroactive tetrathiafulvalene (TTF) unit. The gelation properties of compound 1 were comprehensively evaluated, revealing its ability to immobilize 1,2-dichloroethane and n-butanol, while other solvents tested did not form gels. A series of analyses, including SEM, FTIR, ¹H NMR, and UV/Vis absorption spectroscopy, were conducted to investigate the characteristics of the resulting organogels. The findings indicated that the gelator self-assembled into a three-dimensional supramolecular network, driven by intermolecular hydrogen bonding. As anticipated, the organogels displayed multiple stimuli-responsive sol–gel transitions in response to changes in chemical redox conditions, heating, and the presence of anions due to the dynamic and reversible nature of the non-covalent interactions. Notably, the gelators interacted with various electron acceptor molecules, resulting in the formation of charge transfer (CT) complexes and binary organogels, accompanied by noticeable color changes. Additionally, the gels proved to be effective absorbents, suggesting potential applications for the removal of Rhodamine B cationic dyes from water.