Active template synthesis of topologically chiral and higher order catenanes

Abstract

Mechanically interlocked molecules were first discussed sixty years ago and have since attracted the curiosity of synthetic and supramolecular chemists. This interest first stemmed from the challenge of making such complex molecules, and has since shifted for the interesting properties of the mechanical bond and their applications in many different fields like sensing, catalysis, material science or molecular machines. Furthermore, novel types of stereochemistry can arise from the mechanical bond, which combined with its crowded environment can lead to new and better ligands, sensors or materials. This area of the field is starting to be explored and gaining interest and is ripe for potential applications. The first chapter of this thesis reviews the different types of mechanical stereogenic units and highlights examples of their synthesis and applications. Nonetheless, their enantiopure synthesis is still challenging and some mechanical stereogenic units are yet to be reported. The second chapter of this thesis focuses on improving the synthesis of topologically chiral catenanes and reports the first example of a co-conformationally ‘topologically’ chiral catenane. Finally, the third chapter is dedicated to the study of higher order catenanes. It starts with a review of notable examples, classified by different topologies, that illustrate the strategies towards such complicated molecules. Then, a new active template approach to access linear catenanes with up to four rings is described.

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Identifiers

ORCID for Stephen Goldup: orcid.org/0000-0003-3781-0464

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

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