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Self-assembly of interlocked architectures
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Schergna, Stefano (2002) Self-assembly of interlocked architectures. PhD thesis, University of Warwick.
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Official URL: http://webcat.warwick.ac.uk/record=b3884102
Abstract
An area of great interest is the synthesis and characterisation of molecules possessing moving parts, with the goal that they can act as “molecular machine” carrying out tasks that molecules with fixed conventional architectures cannot do. Rotaxanes and catenanes (mechanically interlocked architectures) represent one approach toward achieving these aims as their component wheels and / or threads are connected together but can still move in certain, controlled directions. This thesis focused on the study of structural rigidity and the preorganisation of thread binding sites as factors of major influence on template efficiency in the synthesis of hydrogen bond assembled supramolecular structures (rotaxanes and catenanes).
Chapter One gives a brief outline of the common synthetic approaches to interlocked architectures (catenanes and rotaxanes) that are now being developed to address the problems outlined above.
Chapter Two and Chapter Three concerns the synthesis of novel amide- based rotaxanes containing various saturated and unsaturated skeletons in their templating core. These new amide-based rotaxanes (muconic, hydromuconic and glutaconic) were synthesised by a clipping strategy in high yields.
Chapter Four concerns the synthesis of a novel class of rotaxanes containing a naphthalene tetramide macrocycle that has a larger cavity (102). Several rotaxanation experiments based on macrocycle 102 precursors and threads containing several possible templating motifs were examined. Chapter Five report on the use of rotaxane wheels as a non-covalent protecting group able to influence the chemical behaviour of the functional groups in the central part of the axle.
Chapter Six several heterocircuit [2]catenanes functionalised with various sulphide groups were synthesised and their monolayer forming capability on a gold surface studied. Another approach involving covalent attachment of macrocycles and catenanes on a pre-formed monolayer was also investigated.
Item Type: | Thesis (PhD) | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Library of Congress Subject Headings (LCSH): | Self-assembly (Chemistry), Molecular machinery, Rotaxanes, Catenanes, Hydrogen bonding | ||||
Official Date: | April 2002 | ||||
Dates: |
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Institution: | University of Warwick | ||||
Theses Department: | Department of Chemistry | ||||
Thesis Type: | PhD | ||||
Publication Status: | Unpublished | ||||
Supervisor(s)/Advisor: | Leigh, David A. | ||||
Format of File: | |||||
Extent: | xviii, 207 leaves | ||||
Language: | eng |
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