Journal
LANGMUIR
Volume 28, Issue 1, Pages 27-30Publisher
AMER CHEMICAL SOC
DOI: 10.1021/la203569y
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Funding
- Research Corporation Cottrell College [CC5549]
- Jesse Ball duPont Foundation
- University of the South
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A twin-tailed glutamate-based lipid with a pyridine headgroup was prepared in good yield using standard amide coupling and protection/deprotection chemistry. The resulting Lewis basic lipid gels a wide array of hydrocarbon solvents at a critical gelation concentration (C-g) of 0.3 wt %. The gelation of more polar solvents, such as ethanol, THF, dichloromethane, and chloroform, occurs with a C-g of between 2 and 5 wt %, demonstrating the importance of hydrogen bonding interactions in gel formation. The importance of hydrogen bonding in this system was also demonstrated by IR observation of the amide bands, which show a substantial shift upon gelation. Solutions of this new organogelator with concentrations below C-g rapidly form gels upon the introduction of a wide variety of metal salts or complexes, providing a convenient general method for the preparation of metallogelators. Spectroscopic evidence suggests that the enhanced gelation seen in the metal-containing systems can be explained by a cross-linking of gel fibril aggregates similar to those formed by the unmetalated gelator.
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