Publication Date

April 2019

Advisor(s)

Brian Northrop

Major

Chemistry

Language

English (United States)

Abstract

Thiol-Michael addition, known as a “click” reaction due to its efficiency and high yields, is useful in the synthesis of macromolecules such as polymers and dendrimers. This reaction is catalyzed by either a base or a nucleophile. Nucleophile catalysis is rapid, but has the potential for byproducts. While base catalysis slower than nucleophile catalysis (though it is still quite fast, maintaining its status as a “click” reaction), it does not lead to any known byproducts. In this study, six potential thiol-Michael catalysts were compared based on their efficiency in catalyzing polymer-polymer ligation and end group functionalization reactions. These six catalysts included two traditional nucleophile catalysts, two traditional base catalysts, and two strong base catalysts, not previously used to catalyze the thiol-Michael reaction. Though the strong base catalysts were expected to be the most efficient, it was found that the nucleophile catalysts were typically most efficient. Further, this study presents initial stages of nucleophile byproduct synthesis with the aim of determining the persistence of this byproduct in the presence of thiolate. Optimization of thiol-Michael reaction catalysis will aid in development of new and improved methods in materials synthesis, particularly of polymers and dendrimers.

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