Date of Award

Fall 12-2020

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry & Biochemistry

Program/Concentration

Chemistry

Committee Director

Guijun Wang

Committee Member

Richard Gregory

Committee Member

Nancy Xu

Committee Member

Jindong Mao

Committee Member

Yaohang Li

Abstract

Carbohydrate based low molecular weight gelators (LMWGs) are biocompatible and have many potential applications. They have been used for drug delivery, environmental clean-up, and for reaction catalysis. In recent years, copper catalyzed azide alkyne cycloaddition reactions (CuAACs) also termed “Click reactions” have shown great applications in the synthesis of various glycoconjugates and carbohydrate derivatives.

In this research, three diverse classes of glycoconjugates (I, II, III) have been designed and synthesized. The first class of compounds (I) in Chapter 2 are D-glucosamine based amide and triazole derivatives with different spacers between the amide and triazole (n=2-5) function groups. These compounds were found to be gelators for organic solvents and aqueous mixtures with polar organic solvents. The gelation properties were analyzed and the factors influencing molecular self-assembling were evaluated. Covalently linking small molecules and forming dendric compounds can result in new classes of supramolecular gelators with enhanced intermolecular interactions. Using pentaerythritol and dipentaerythritol as the core building blocks, several glycoconjugates (II) were synthesized and characterized in Chapter 3. These glycoconjugates showed structure correlation with molecular self-assembly and gelation. The resulting gels were characterized using optical microscopy and rheology. Some effective gelators were also used for drug delivery study and for catalyzing CuSO4 mediated click reactions. In the Chapter 4 (III), bis-triazole containing glycomacrocycles were synthesized using click chemistry, these macrocycles include both α and β anomers of D-glucosamine derivatives. The various macrocycles are being studied for their complexation properties with anions and other guest molecules. They may also have biological activities as enzyme inhibitors.

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DOI

10.25777/rbrk-y329

ISBN

9798557053662

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