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Publication Date

Spring 2011

Degree Type

Thesis - Campus Access Only

Degree Name

Master of Science (MS)

Department

Chemistry

Advisor

Marc d'Alarcao

Subject Areas

Chemistry

Abstract

Polymers have a variety of properties that have been exploited for controlled drug delivery applications. However, release on command is rarely achievable. A novel strategy has been designed for "on-command" controlled drug release based on the degradation of polymers triggered by electrical current. We have designed an electrochemically degradable crosslinking reagent (EDCR) comprised of a bi-functional polymer cross-linking moiety and an electroactive core that undergoes degradation under reductive conditions. The EDCR consists of a quinone moiety with two alkyl arms each bearing an amide or ester linkage connecting to the crosslinking moiety. Polymers cross-linked with EDCR are expected to degrade when reduced, thereby providing control over the degradation of the polymer and the release of an entrapped drug. In this work, EDCR with divinylbenzene-like ends has been synthesized, and its degradation has been studied using electrochemical experiments. It has been successfully used to crosslink polystyrene (PS). EDCR with divinylsulfone-like ends has also been synthesized and has been used to crosslink carboxymethylcellulose (CMC). Electrochemical experiments conducted on EDCR-crosslinked polystyrene at electric potentials between 0 to -0.9 V, have confirmed the degradation of the polymer.

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