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Supramolecular aspects of fluorine chemistry in self-assembled monolayers
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Pinfold, Harry (2021) Supramolecular aspects of fluorine chemistry in self-assembled monolayers. PhD thesis, University of Warwick.
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Official URL: http://webcat.warwick.ac.uk/record=b3756283
Abstract
The role of non-covalent interactions involving fluorine atoms is of significant interest in the field of supramolecular chemistry, with particular focus being invested into understanding the role such interactions have in medicinal chemistry and three-dimensional solid-state materials. Although the formation of two-dimensional surface-confined networks is largely governed by the same principles of supramolecular chemistry as the aforementioned fields, the potential value of interactions involving fluorine within these systems has been little studied. In this thesis, the supramolecular role of fluorine atoms within two-dimensional surface-confined networks is systematically explored. Scanning tunnelling microscopy is used to investigate the ability of an array of fluorinated molecular building blocks to self-assemble into two-dimensional surface-confined networks. The arrangement of the molecular building blocks within the resultant networks gives insight into the structural role of the intermolecular interactions at play. Specific insight into the significance of the fluorine atoms is obtained by comparing the self-assembly behaviour of the fluorinated building blocks with that of their unfluorinated structural analogues. Although some focus is given to simple homomolecular systems, particular emphasis is devoted to investigating the role of fluorination in promoting the formation of complex multicomponent networks. In some of the systems studied, the presence of fluorine atoms is found to have a minimal impact, with isostructural networks being observed with both the fluorinated and unfluorinated analogues. However, in other systems the fluorine atoms are found to play a very prominent role. This is rationalised as being due to a combination of weak intermolecular interactions in which the fluorine atoms can directly partake and the ability of fluorination to augment other intermolecular interactions, such as hydrogen bonds. In particular, fluorination is found to promote the formation of carboxyl–pyridyl and phenol–pyridyl hydrogen bonding interactions, the former of which is rarely observed in two-dimensional surface-confined networks and the latter of which has hitherto not been observed.
Item Type: | Thesis (PhD) | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Library of Congress Subject Headings (LCSH): | Self-assembly (Chemistry), Fluorine, Fluorination, Intermolecular forces | ||||
Official Date: | July 2021 | ||||
Dates: |
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Institution: | University of Warwick | ||||
Theses Department: | Department of Chemistry | ||||
Thesis Type: | PhD | ||||
Publication Status: | Unpublished | ||||
Supervisor(s)/Advisor: | Costantini, Giovanni | ||||
Format of File: | |||||
Extent: | vi, 144 leaves : illustrations | ||||
Language: | eng |
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