Synthesis and applications of mechanically interlocked molecules

Abstract

Mechanically interlocked molecules were firstly described in the 1960s and have since become the centre of the attention for many chemists. These molecules show different interesting aspects such as the synthetic challenges, the potential applications in sensing, catalysis and molecular machines, and the exclusive stereochemistry of those molecules. In this thesis, the first chapter briefly reviews the different approaches adopted for the formation of the mechanical bond with particular emphasis on the recent developments of the active template approach. The second chapter describes the synthesis of a mechanically interlocked molecule able to act as a metal ligand for catalysis. The third chapter is focused on the development of a new strategy for the diastereoselective synthesis of topologically chiral catenanes and the application of this strategy to the synthesis of the first co-conformationally “topologically” chiral. The fourth chapter describes the optimisation of the diastereoselective synthesis of mechanically axially chiral rotaxanes and the extension of the methodology to the direct enantioselective synthesis. Finally, the last chapter describes a study of the factors influencing the selectivity of the synthesis of the under-explored mechanically geometric isomeric rotaxanes and catenanes as well as the description and diastereoselective synthesis of a new form of mechanically geometrically isomeric rotaxanes.

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ORCID for Darren Bradshaw: orcid.org/0000-0001-5258-6224

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