Synthesis of Multi-Responsive Polymers of Boronic Acid Derivatives and Their Applications

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Synthesis of Multi-Responsive Polymers of Boronic Acid Derivatives and Their Applications
Jeong, Eun Sun
Ryu, Ja-Hyoung
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Graduate School of UNIST
Stimuli-responsive polymers alter their chemical and physical properties upon recognition of external stimuli such as temperature, pH, light and the presence of specific molecules. These polymers and their block copolymers have attracted attention for their possible applications as drug delivery vehicles, hydrogels, and self-healing materials. In particular, organoboronic acid and its derivatives are important synthetic molecules that are currently used as antifungal reagents and reagents for cross-coupling. Polymers containing derivatives of organoboronic acid and their block copolymers are receiving recent interest because of their ability to recognize important natural diol compounds such as saccharides and nucleotides under biologically relevant conditions. The reversible binding of diol compounds to organoboronic acid moieties triggers the change of their physical properties such as solubility in water. Therefore, it is an important task to develop new polymers and block copolymers that can respond to the presence of diols at low concentration in solution. These new polymers and block copolymers could be useful for the smart materials for the development of sensor and drug delivery system for glucose related human diseases such as diabetes. In this dissertation, I describe the synthesis of new monosaccharide-responsive polymers composed of random copolymers of organoboronic acid-containing monomers and a variety of monomers possessing stimuli-responsiveness toward temperature and pH. To synthesize well-defined polymers and block copolymers, controlled polymerization techniques, such as reversible addition-fragmentation chain transfer polymerization, and ring-opening polymerization, were investigated. By these synthetic procedures, monomers having responsiveness toward desired external stimuli were combined to the benzoboroxole-containing monomers to form multi-responsive polymers and block copolymers. The reversible binding of the resulting polymers with diols such as monosaccharides and adenosine-triphosphate was studied by turbidity test. The controlled polymerization techniques with these monomers allowed us to synthesize block copolymers having well-defined molecular weights and architectures. The block copolymers could be self-assembled into glucose-responsive micelles or vesicles. These structures showed glucose triggered disassembly under physiologically relevant pH condition and glucose levels. Due to the presence of hydrophilic solubilizing group between the solubility-switching organoboronic acid derivatives in the membrane-forming block, the structures of block copolymers responded to a lower level of glucose in the medium. The vesicles containing organoboronic acid derivatives can encapsulate water soluble molecules such as insulin. That results the monosaccharide responsive block copolymers could be utilized as new drug delivery vehicles for cargo molecules such as insulin.
Department of Chemistry
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