Synthesis of a Series of Trimeric Branched Glycoconjugates and Their Applications for Supramolecular Gels and Catalysis

Carbohydrate-derived molecular gelators have found many practical applications as soft materials. To better understand the structure and molecular gelation relationship and further explore the applications of sugar-based gelators, we designed and synthesized eight trimeric branched sugar triazole de...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2023-08, Vol.28 (16), p.6056
Main Authors: Bietsch, Jonathan, Chen, Anji, Wang, Dan, Wang, Guijun
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Azide
Carbohydrates
Catalysis
Chemical properties
click chemistry
Copper
Dextrose
Environmental restoration
Ethanol
Galactose
Glucose
glycoclusters
glycoconjugates
green synthesis
Ligands
Morphology
Rheology
Solvents
Sugars
Technology application
Triazoles
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Summary:Carbohydrate-derived molecular gelators have found many practical applications as soft materials. To better understand the structure and molecular gelation relationship and further explore the applications of sugar-based gelators, we designed and synthesized eight trimeric branched sugar triazole derivatives and studied their self-assembling properties. These included glucose, glucosamine, galactose, and maltose derivatives. Interestingly, the gelation properties of these compounds exhibited correlations with the peripheral sugar structures. The maltose derivative did not form gels in the tested solvents, but all other compounds exhibited gelation properties in at least one of the solvents. Glucose derivatives showed superior performance, followed by glucosamine derivatives. They typically formed gels in toluene and alcohols; some formed gels in ethanol-water mixtures or DMSO water mixtures. The glycoclusters 9 and 10 demonstrated rate acceleration for the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. These were further studied for their metallogels formation properties, and the copper metallogels from compound 9 were successfully utilized to catalyze click reactions. These metallogels were able to form a gel column, which was effective in converting the reactants into the triazole products in multiple cycles. Moreover, the same gel column was used to transform a second click reaction using different reactants. The synthesis and characterization of these compounds and their applications for catalytic reactions were discussed.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28166056