Synthesis and Self-Assembling Properties of Peracetylated β-1-Triazolyl Alkyl D-Glucosides and D-Galactosides

Abstract

Carbohydrate-based low-molecular-weight gelators (LMWGs) are useful classes of compounds due to their numerous applications. Among sugar-based LMWGs, certain peracetylated sugar beta-triazole derivatives were found to be effective organogelators and showed interesting self-assembling properties. To further understand the structural influence towards molecular assemblies and obtain new functional materials with interesting properties, we designed and synthesized a library of tetraacetyl beta-1-triazolyl alkyl-D-glucosides and D-galactosides, in which a two or three carbon spacer is inserted between the anomeric position and the triazole moiety. A series of 16 glucose derivatives and 14 galactose derivatives were synthesized and analyzed. The self-assembling properties of these new triazole containing glycoconjugates in different solvents were analyzed. Several glucose derivatives were found to be effective LMWGs, with compound 7a forming gels in a variety of organic solvents as well as in the presence of metal ions in aqueous solutions. The organogels formed by several compounds were characterized using optical microscopy, atomic force microscopy (AFM) and UV-vis spectroscopy, etc. The co-gels formed by compound 7a with the Fmoc derivative 7i showed interesting fluorescence enhancement upon gelation. Several gelators were also characterized using powder X-ray diffraction and FT-IR spectroscopy. The potential applications of these sugar-based gelators for drug delivery and dye removal were also studied.

4,6-O-Phenylethylidene Acetal Protected D-Glucosamine Carbamate-Based Gelators and Their Applications for Multi-Component Gels

“…Fluorescence emission spectra were obtained using the Shimadzu RF-6000 Spectro Fluorophotometer with excitation and emission bandwidths set at 5.0 nm and a scan speed of 600 nm/min. The gelation tests, optical microscopy, and AFM imaging were carried out following a literature report [ 46 ]. The instruments used for optical microscopy was the Olympus BX60M optical microscope and the Olympus DP73-1-51 high-performance 17MP digital camera with pixel shifting and Peltier cooling.…”

Harnessing Glycolipids for Supramolecular Gelation: A Contemporary Review

“…Further, these hydrogels were implemented to study the controlled release of chloramphenicol and entrapment of dye. 105,106 A series of phenylboronic esters-based glycolipids were prepared using phenylboronic acid and alkylglucosides in a single step. After evaluating their gelation behavior, it was observed that these soft materials can be used for controlled release and drug delivery [Figure 14, (28)].…”

“…A series of glycolipids was prepared, and their gelation and self-assembling characteristics were studied, along with the effect of structural variations. Further, these hydrogels were implemented to study the controlled release of chloramphenicol and entrapment of dye. , …”

“…Further, these hydrogels were implemented to study the controlled release of chloramphenicol and entrapment of dye. 105 , 106 …”

Sugar isoxazole based hydrogelators and their applications as reusable hydrogels for dye removal

“…5 The beta-glucosyl derivatives with triazole functional group linked through a 2 carbon spacer were also reported, some of the compounds are organogelators but the structure flexibility tend to make the molecules more soluble and less prone to form gels. 6 Isoxazoles are five membered ring heterocycles which can be synthesized via 2+3 cycloaddition reactions. 7,8 We envisioned that the nitrogen and oxygen containing isoxazole heterocycle could be used for the design of sugar based molecular gelators through modification of template B.…”