Publication Date

April 2015

Advisor(s)

Brian Northrop

Major

Chemistry

Language

English (United States)

Abstract

Organic synthesis deals with the construction of complex organic compounds via a variety of chemical pathways. Mechanical bonding is a unique method of joining two molecules, often likened to the key in a key chain analogy. Polymers are ubiquitous and exhibit characteristic bulk properties that differ from their starting monomers. This thesis discusses the combined utilization of these three disciplines in order in order to reach our ultimate goal of synthesizing a mechanically interlocked polymer. Interlocked molecules are known to have many useful functions, but this research focuses on incorporating mechanically interlocked molecules into a polymer system using thiol-ene click chemistry, thereby yielding mechanically interlocked polymers, which are expected to have their own unique properties, such as resistance to stress. The mechanically interlocked molecule is a rotaxane, which is structured as a dumbbell shaped molecule threaded through a large cyclic ring, or macrocycle. The bulky ends of the dumbbell are called stoppers, which prevent the ring from falling off. Synthesis of these stoppers is discussed in this thesis, and they are an integral part of rotaxane functionality. 1H NMR and thin layer chromatography (TLC) were used to characterize each step in stopper synthesis, as well as verify stopper effectiveness. Computational chemistry assists wet chemistry to provide insight into rotaxane test results and future synthetic stopper design. When we reach the cross-linking stage, characterization of the mechanically interlocked polymer will reveal its unique properties and give greater insight into its potential applications across materials science.

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