Yates, Jennifer (2012) Rotaxane synthesis via the 'threading followed by stoppering' approach. PhD thesis, University of Warwick.

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Abstract

The development of template directed synthesis towards the formation of interlocked
architectures has allowed for the synthesis of a variety of rotaxanes. Chapter 1 covers the
history of rotaxanes including their nomenclature and methods of formation. An overview of
the intermolecular interactions used to facilitate the synthesis of these architectures is
described and examples of template directed synthesis and properties of rotaxanes are
discussed.
In Chapter 2 the use of the Diels-Alder reaction towards formation of rotaxanes in a
‘threading followed by stoppering’ protocol is covered. The synthesis of [n]rotaxanes is
described with secondary ammonium ions, a novel perimidine benzimidazole and
bispyridinium binding templates integrated into threads.
In Chapter 3 a novel binding template was developed, incorporating a triazole into a
dibenzylammonium binding motif. Binding studies were carried out and [n]rotaxanes were
synthesised using this motif with the groups Diels-Alder ‘threading followed by stoppering’
protocol.
Chapter 4 discusses the modification of the DB24C8 macrocycle with the aim to enhance
binding interactions with a variety of binding motifs. Two macrocycles were successfully
synthesised and their binding affinities calculated with known and novel binding templates
investigated in the previous chapters.
The work in this thesis shows a Diels-Alder stoppering reaction can be successfully used to
synthesise [n]rotaxanes with a variety of binding templates including novel templates
discovered during this project. During the work it was also revealed that modifications to
known binding templates can provide an enhancement in binding interactions in comparison
to their unmodified predecessors.

Item Type:	Thesis or Dissertation (PhD)
Subjects:	Q Science > QD Chemistry
Library of Congress Subject Headings (LCSH):	Rotaxanes -- Synthesis, Diels-Alder reaction
Official Date:	July 2012
Dates:	Date Event July 2012 Submitted
Institution:	University of Warwick
Theses Department:	Department of Chemistry
Thesis Type:	PhD
Publication Status:	Unpublished
Supervisor(s)/Advisor:	Clarkson, Guy J.
Sponsors:	University of Warwick
Extent:	xxii, 281 leaves : illustrations
Language:	eng

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