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Publication Date

Spring 2013

Degree Type

Thesis - Campus Access Only

Degree Name

Master of Science (MS)




Marc d'Alarcao

Subject Areas



The goal of this research was to design, synthesize, and manipulate polymer crosslinkers that contained groups that degraded in response to stimuli. A quinone-based electrochemically degradable polymer crosslinking reagent (EDCR) with labile ester bonds was prepared and it was used to crosslink carboxymethylcellulose-hydroxyethylcellulose (CMC-HEC) to prepare hydrogels. Chemical or electrochemical reduction of the quinone to a hydroquinone initiated a rapid cyclization reaction accelerated by the "tri-alkyl lock phenomenon." Cyclization broke the crosslinks, causing the hydrogel to revert to CMC's original soluble form. The efficiency and rates of degradation of the hydrogels upon chemical and electrochemical reduction were measured. A polymer whose material properties could be switched electrochemically may have many uses and applications in medicine and biotechnology.