Synthesis and applications of functional interlocked molecules: anion-π catalysis and mechanically chiral structures

Abstract

Mechanically interlocked molecules (MIMs) have progressed from synthetic curios to readily accessible structures due to the development of high yielding “templated” syntheses. MIMs are able to display molecular chirality in the absence of traditional covalent stereogenic units, and recent studies have begun to investigate effective synthetic approaches to these “mechanically chiral” molecules that avoid chiral stationary phase HPLC separations of products, allowing their potential applications in catalysis, sensing and materials applications to be assessed without the prohibitive cost and scale limitations associated with CSP-HPLC. This thesis describes work to expand the applications of MIMs prepared via an active template approach. In the first chapter, the progress made in the synthesis of mechanically chiral molecules is summarised. In the second, a study on the functional group tolerance of a Ni-mediated macrocyclisation reaction is described. In the third, the application of rotaxanes as anion-π catalysts is explored. Finally, in the fourth chapter, a stereoselective synthesis of mechanically axially chiral catenanes is developed.

More information

Identifiers

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

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

Catalogue record

Export record