Remarkable solvent isotope dependence on gelation strength in low molecular weight hydro-gelators
| Autor: | Wesley R. Browne, Tjalling R Canrinus, Florian J R Cerpentier, Ben L. Feringa |
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| Přispěvatelé: | Molecular Inorganic Chemistry, Synthetic Organic Chemistry, Basic and Translational Research and Imaging Methodology Development in Groningen (BRIDGE) |
| Rok vydání: | 2017 |
| Předmět: |
MECHANISM
Cyclohexane Carboxylic acid Ionic bonding 02 engineering and technology 010402 general chemistry 01 natural sciences Catalysis Hydrophobic effect C-3-SYMMETRICAL MOLECULES chemistry.chemical_compound DESIGN Materials Chemistry Organic chemistry Molecule WATER SURFACTANTS HYDROGELATORS chemistry.chemical_classification Chemistry Hydrogen bond Metals and Alloys SUPRAMOLECULAR POLYMERIZATION General Chemistry 021001 nanoscience & nanotechnology 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials Solvent Chemical engineering Self-healing hydrogels Ceramics and Composites POLYMERS 0210 nano-technology |
| Zdroj: | Chemical communications (Cambridge, England), 53(10), 1719-1722. ROYAL SOC CHEMISTRY |
| ISSN: | 1364-548X 1359-7345 |
| Popis: | A delicate interplay of anisotropic hydrophobic/hydrophilic, π-π stacking, ionic and hydrogen bond interactions determine the strength of hydrogelators and are considered key factors in efforts to design potent small molecule hydrogelators. Here we show that solvent deuteration and electrolytic strength affect the strength of hydrogels formed from amino acid modified C3-symmetric cyclohexane trisamides profoundly. Gels formed by self-assembly through heating/cooling of solutions or by pH switching show up to a 30 °C increase in their melting temperatures in D2O compared to H2O. The unusually large solvent isotope effect on gel formation and thermal properties indicates that, in contrast to expectations, hydrogen bonding is not the primary determinant of gel strength but instead that hydrophobic interactions between the gelator molecules and the terminal carboxylic acid units are of greater importance. A conclusion that is supported by a similarly large effect of electrolytes on gel strength. |
| Databáze: | OpenAIRE |
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