Yeung, Angus 
ORCID: 0009-0006-9652-8716
(2025).
Chiral perylene diimide containing macrocycles and rotaxanes.
University of Birmingham.
Ph.D.
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Yeung2025PhD.pdf
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Abstract
This thesis describes an investigation into a class of chiral organic dyes, perylene diimides (PDIs). Specifically, configurationally stable PDI dyes are targeted through the design, synthesis and analysis of PDI-based macrocycles and rotaxanes.
Chapter One introduces PDIs and outlines how the synthetic diversity of PDI derivatives impacts their photophysical, redox, supramolecular and chiral properties, with a particular focus on the integration of PDIs into macrocycles and rotaxanes.
Chapter Two describes the design and synthesis of a series of novel chirally-locked PDI-based macrocycles, including an investigation into kinetic templation in the macrocyclisation reaction. The successful synthesis of PDI-based macrocycles with πelectron donors in the macrocycle linkers evidences the importance of π-π donor-acceptor interactions.
Chapter Three explores kinetic templation in PDI-based macrocycles containing a second chiral aromatic component. Here, the diastereoselective synthesis of a PDI-based macrocycle is realised, in which templating non-covalent interactions between the aromatic units that direct the outcome of the dynamic kinetic resolution are discussed.
Chapter Four describes the progress towards a configurationally stable chiral PDI through mechanical bonding by the synthesis of a novel [3]rotaxane containing a PDI-based axle and two macrocycle components. When positioned in close proximity to the chiral PDI, the macrocycles are shown to slow down PDI atropisomer interconversion. The pH-induced molecular shuttling of these macrocycles is also presented.
Chapter Five describes the experimental procedures used throughout this work and details the characterisation of novel compounds.
Chapter Six provides a summary of the major conclusions from the research described in this thesis.
| Type of Work: | Thesis (Doctorates > Ph.D.) | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Award Type: | Doctorates > Ph.D. | |||||||||
| Supervisor(s): |
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| Licence: | All rights reserved | |||||||||
| College/Faculty: | Colleges > College of Engineering & Physical Sciences | |||||||||
| School or Department: | School of Chemistry | |||||||||
| Funders: | Engineering and Physical Sciences Research Council | |||||||||
| Subjects: | Q Science > QD Chemistry | |||||||||
| URI: | http://etheses.bham.ac.uk/id/eprint/15893 |
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