| This Dissertation describes the development of the synthesis of mechanically interlocked molecules, beginning with the initial statistical syntheses of [2]catenanes and [2]rotaxanes, through advanced methods aimed at synthesizing complex molecular structures such as Borromean rings and suit[n]anes. Chapter 1 chronicles the successful use of donor/acceptor-based supramolecular interactions to drive the synthesis of functional molecular switches, muscles, and a molecular elevator. Chapter 2 describes two different strategies aimed at synthesizing the elusive hydrogen-bonding based Borromean rings, by virtue of ammonium-binding interactions. With their unique topology in which three mutually interlocked rings must be brought together in a highly-specific fashion, the Borromean rings are a formidable synthetic challenge. In Chapter 3, dynamic covalent chemistry is used to synthesize a family of mechanically interlocked molecules, including a bridged [2]rotaxane, a doubly-bridged [2]rotaxane, a cyclic [3]rotaxane, a doubly-bound [2]pseudorotaxane, and a branched [2]rotaxane, all from a dynamic covalent library. Through the ongoing development of dynamic synthetic techniques, it is possible to synthesize molecules of greater structural complexity in high yields and with fewer synthetic steps. Thus, this work aids in the development of the next generation of synthetic methods necessary to build functional molecular scaffolds. |
