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Title: Halogen- and hydrogen-bonding cyclic and interlocked hosts for anion recognition and sensing
Author: Gilday, Lydia C.
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2013
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This thesis describes the synthesis of macrocyclic and interlocked receptors which exploit halogen- and hydrogen-bonding intermolecular interactions for anion recognition. Chapter One introduces the field of supramolecular chemistry, with particular focus on applications of host–guest chemistry to anion coordination and anion templation in the construction of mechanically interlocked molecules. Chapter Two details the synthesis of a series of cyclic and cage-like porphyrin-based receptors which bind anions through halogen- and hydrogen-bonding interactions. The ability of these receptor systems to bind and sense anionic guest species is investigated and comparisons between hydrogen- and halogen-bonding are discussed. Chapter Three reports anion-templated pseudorotaxane assemblies stabilised by both halogen- and hydrogen-bonding. The related catenanes are also prepared and their affinity for anions is investigated. The first examples of interpenetrated and interlocked architectures constructed by a single charge-assisted halogen bond are also reported. Chapter Four describes the synthesis of a 1,3-dialkyl-1,2,3-triazolium-containing threading component, whose anion binding properties are studied and compared with other threading molecules. The ability of this novel thread to form pseudorotaxanes is investigated and the preparation of the related rotaxane species is outlined. Chapter Five discusses attempts to prepare rotaxanes with improved anion binding affinities through increasing the lipophilicity of the anion binding clefts. Several novel rotaxanes are described and their anion binding properties are probed. Chapter Six describes the experimental procedures used in this work and the characterisation of compounds presented in chapters two to five. Chapter Seven summarises the conclusions of this thesis.
Supervisor: Beer, Paul Sponsor: EPSRC
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Supramolecular chemistry ; Anions--Spectra ; Hydrogen bonding ; Macrocyclic compounds