General approach to low-molecular-weight metallogelators via the coordination-induced gelation of an L-glutamate-based lipid |
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Authors: | Bachman Robert E Zucchero Anthony J Robinson Jamie L |
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Institution: | Department of Chemistry, The University of the South, 735 University Avenue, Sewanee, Tennessee 37383, United States. rbachman@sewanee.edu |
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Abstract: | 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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