Abstract
Carbohydrate-based low molecular weight gelators (LMWGs) exhibit many desirable properties making them useful in various fields including applications as drug delivery carriers. In order to further understand the structural connection to gelation properties, especially the influence of halide substitutions, we have designed and synthesized a series of para-chlorobenzylidene acetal protected D-glucosamine amide derivatives. Fifteen different amides were synthesized, and their self-assembling properties were assessed in multiple organic solvents, as well as mixtures of organic solvents with water. All derivatives were found to be gelators for at least one solvent and majority formed gels in multiple solvents at concentrations lower than 2 wt%. A few derivatives rendered remarkably stable gels in aqueous solutions at concentrations below 0.1 wt%. The benzamide 13 formed gels in water and in EtOH/H2O (v/v 1:2) at 0.36 mg/mL. The gels were characterized using optical microscopy and atomic force microscopy, and the self-assembly mechanism was probed using variable temperature 1H-NMR spectroscopy. Gel extrusion studies using H2O/DMSO gels successfully printed lines of gels on glass slides, which retained viscoelasticity based on rheology. Gels formed by the benzamide 13 were used for encapsulation and the controlled release of chloramphenicol and naproxen, as well as for dye removal for toluidine blue aqueous solutions.
Highlights
Introductionlow molecular weight gelators (LMWGs) systems typically form one dimensional self-assembled fibers, which interact with each other to create intricate networks
Carbohydrate-based low molecular weight gelators (LMWGs) are small molecules with the ability to self-assemble into three dimensional structures that entrap surrounding solvent, creating solid-like materials known as supramolecular gels
The synthesis of the 4,6-O-(p-chlorobenzylidene) acetal-functionalized D-glucosamine amide derivatives is shown in Scheme 1
Summary
LMWG systems typically form one dimensional self-assembled fibers, which interact with each other to create intricate networks. The design and study of sugar based gelators have attracted much attention. They have been explored for applications in several research fields ranging from drug delivery [5,6,7,8], to environmental applications [9,10,11,12,13,14], enzyme immobilization, ion sensing [15,16,17], and supramolecular gel catalysts [18,19,20]
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