Versatile Supramolecular Gelators That Can Harden Water, Organic Solvents and Ionic Liquids

• Published in: Langmuir Vol. 28; no. 25; pp. 9259 - 9266
• Main Authors: Minakuchi, Nami, Hoe, Kazuki, Yamaki, Daisuke, Ten-no, Seiichiro, Nakashima, Kazunori, Goto, Masahiro, Mizuhata, Minoru, Maruyama, Tatsuo
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 26.06.2012
• Subjects: Chemistry; Electrochemistry; Exact sciences and technology; General and physical chemistry; Gluconic acid; Water; Self assembly; Molecular packing; Scanning electron microscopy; Molecular structure; Gelation; Ionic conductivity; Nanofiber; High temperature; Hydrophobicity; Liquid phase; Small angle X ray scattering; Edible oil; Ionic liquid; Organic solvent; Transmission electron microscopy; Synthesis; Aminoacid; Electrochemistry; Density functional method; pH; Aqueous solution
• ISSN: 0743-7463; 1520-5827
• DOI: 10.1021/la301442f

We developed novel supramolecular gelators with simple molecular structures that could harden a broad range of solvents: aqueous solutions of a wide pH range, organic solvents, edible oil, biodiesel, and ionic liquids at gelation concentrations of 0.1–2 wt %. The supramolecular gelators were composed of a long hydrophobic tail, amino acids and gluconic acid, which were prepared by liquid-phase synthesis. Among seven types of the gelators synthesized, the gelators containing l-Val, l-Leu, and l-Ile exhibited high gelation ability to various solvents. These gelators were soluble in aqueous and organic solvents, and also in ionic liquids at high temperature. The gelation of these solvents was thermally reversible. The microscopic observations (TEM, SEM, and CLSM) and small-angle X-ray scattering (SAXS) measurements suggested that the gelator molecules self-assembled to form entangled nanofibers in a large variety of solvents, resulting in the gelation of these solvents. Molecular mechanics and density functional theory (DFT) calculations indicated the possible molecular packing of the gelator in the nanofibers. Interestingly, the gelation of an ionic liquid by our gelator did not affect the ionic conductivity of the ionic liquid, which would provide an advantage to electrochemical applications.