Macrocyclic, inter-penetrated and interlocked triazole and triazolium containing anion receptors

Thesis

This thesis describes the synthesis of macrocyclic, interpenetrated, and in particular, interlocked anion receptors containing the triazole and triazolium motifs.

Chapter One introduces the field of supramolecular chemistry with a focus on the areas of particular relevance to this thesis, namely anion coordination, anion templation and the synthesis of interlocked structures.

Chapter Two describes the preparation of acyclic and macrocyclic neutral bis-triazole receptors, and a study of their anion and transition metal cation recognition properties. The synthesis of an acyclic anion receptor incorporating the novel pyridinium-3,5-bis(triazole) motif is also reported. Chapter Three details the incorporation of the pyridinium bis-triazole motif into pseudorotaxanes, catenanes and rotaxanes. A thorough study of the use of a variety of anions, including oxoanions, to template interpenetrated assemblies is described, and the anion binding a nities of the catenane and rotaxane hosts discussed in comparison to analogous amide based systems.

Chapter Four presents research into a series of triazolium containing rotaxanes. A number of structural modifications are made to the interlocked host molecules, and the effect of these changes on the anion recognition properties of the receptors is discussed.

Chapter Five investigates the incorporation of two or more cationic triazolium groups into cyclic and interlocked host systems in order to create highly charged receptors capable of anion recognition in aqueous media.

Chapter Six describes experimental procedures used in this work, and details the characterization of novel compounds.

Chapter Seven summarizes the major conclusions of this thesis.

Chapter Eight contains the references cited within Chapters One to Six.

Authors: White, N; Nicholas White

• Publication date: 2013
• DOI: 10.5287/ora-vyedjba8g
• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: University of Oxford
• Language: English
• Keywords: Chemistry; organic; pseudorotaxanes; inorganic; rotaxanes; supramolecular; catenanes; anions
• Subjects: Inorganic chemistry