General Approach to Low-Molecular-Weight
Metallogelators
via the Coordination-Induced Gelation of an l-Glutamate-Based
Lipid
Version 4 2017-11-17, 19:18
Version 3 2017-10-20, 18:49
Version 2 2017-10-20, 17:49
Version 1 2016-02-22, 09:37
Posted on 2017-11-17 - 19:18
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 (Cg) of 0.3 wt %. The gelation of more polar solvents, such as
ethanol, THF, dichloromethane, and chloroform, occurs with a Cg 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 Cg 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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Bachman, Robert E.; Zucchero, Anthony J.; Robinson, Jamie L. (2016). General Approach to Low-Molecular-Weight
Metallogelators
via the Coordination-Induced Gelation of an l-Glutamate-Based
Lipid. ACS Publications. Collection. https://doi.org/10.1021/la203569y
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AUTHORS (3)
RB
Robert E. Bachman
AZ
Anthony J. Zucchero
JR
Jamie L. Robinson