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

Synthesis and applications of functional interlocked molecules: anion-π catalysis and mechanically chiral structures
Synthesis and applications of functional interlocked molecules: anion-π catalysis and mechanically chiral structures
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.
University of Southampton
Maynard, John, Robert James
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Maynard, John, Robert James
4e09e766-1294-4056-8bff-4277874f0495
Goldup, Stephen
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Bradshaw, Darren
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Maynard, John, Robert James (2021) Synthesis and applications of functional interlocked molecules: anion-π catalysis and mechanically chiral structures. Doctoral Thesis, 290pp.

Record type: Thesis (Doctoral)

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.

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Published date: April 2021

Identifiers

Local EPrints ID: 450214
URI: http://eprints.soton.ac.uk/id/eprint/450214
PURE UUID: 99b9c774-cd0f-47c6-8a44-bb3c4a10df8d
ORCID for Stephen Goldup: ORCID iD orcid.org/0000-0003-3781-0464
ORCID for Darren Bradshaw: ORCID iD orcid.org/0000-0001-5258-6224

Catalogue record

Date deposited: 15 Jul 2021 16:53
Last modified: 21 Mar 2024 05:01

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Contributors

Author: John, Robert James Maynard
Thesis advisor: Stephen Goldup ORCID iD
Thesis advisor: Darren Bradshaw ORCID iD

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