Abstract
The dimer l-lysine derivatives, in which two Nα,Nε-diacyl-l-lysines were crosslinked by calcium ion, were synthesized through a simply synthetic procedure and their gelation properties were examined. These compounds functioned as an organogelator; especially, the gelators possessing both a linear and a branched alkyl chains had the better organogelation ability and formed the thermally stable and rigid organogel. In addition, some organogels had a thixotropic property, which were responsive to a mechanical stimulus and reversibly underwent the gel–sol transition at room temperature. The thixotropic behavior was confirmed by visual contact and rheological experiments. Furthermore, it was assumed the mechanism of the thixotropic behavior.
Highlights
There has been a great study on a low-molecular-weight gelator and its gel over the past decades, because of its academic interests and potential applications to cosmetics, foods, medical and pharmaceutical, photonic and electronic devices [1,2,3,4,5,6,7,8,9,10]
We describe the supramolecular organogelation of new L-lysine-based low-molecular-weight gelators and thixotropic properties of the supramolecular gels
A and B were easier to handle for the gel formation. These results indicate that the alkyl group at Nα position on the lysine plays an important role in the organogelation
Summary
There has been a great study on a low-molecular-weight gelator and its gel (supramolecular gel) over the past decades, because of its academic interests and potential applications to cosmetics, foods, medical and pharmaceutical, photonic and electronic devices [1,2,3,4,5,6,7,8,9,10]. The gelator molecules randomly self-assemble into the three-dimensional networks, involving the formation of nanofibers (one-dimensional aggregates). Weiss et al reported the thixotropic organogels formed by the spherulitic self-assembled fibrillar networks [21]. Shinkai et al prepared the thixotropic gels that the gelators self-assembled into disk-like aggregates [26]. The gelators form a one-dimensional aggregate (supramolecular polymer) through strong hydrogen bonding interaction between the cyclodipeptide segments and create a three-dimensional network by weak interaction of van der Waals force between the side chain segments; the shearing breaks the weak van der Waals interaction (but not the strong hydrogen bonding interaction), and the gel readily collapses. We describe the supramolecular organogelation of new L-lysine-based low-molecular-weight gelators and thixotropic properties of the supramolecular gels
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