Diquinoline molecules have been shown previously to have interesting inclusion properties. Of the nine new, targeted molecules produced for this work, seven formed inclusion compounds, and their solid-state structures are discussed herein. Chapter 2 shows the effect that substituting a hydrogen atom with a chlorine atom has on the inclusion properties. This comes about because of the additional intermolecular attractions that are now possible, and a wider range of guest molecules is included as a result. A new homochiral aromatic 'swivel offset face-face (OFF)' interaction is observed. Chapters 3 and 4 deal with the effect of adding extra aromatic planes to the target molecules, two or four planes, respectively. Each of these host molecules formed dimeric host-host units that are extremely similar across all crystal structures. These dimers mainly employed aromatic edgeface (EF) interactions. Chapter 5 looks at the effect of combining the modifications described in Chapters 2-4, namely additional aromatic surfaces and atom substitution. The resulting host molecule specifically includes polyhalomethane guests. In addition, this host molecule formed two concomitant pseudo-dimorph compounds with chloroform-d. The diquinoline host molecule presented in Chapter 6 incorporated an isomeric central linker ring to the other compounds. Although only a single crystal structure could be obtained, 1H NMR spectroscopy experiments show other small aromatics may be included. The effect of electron donating chemical substituents was examined in Chapter 7. These compounds were found to be quite insoluble, and did not produce crystals suitable for X-ray analysis. The host molecules in Chapter 8 contain electron withdrawing nitro groups. The two isomeric compounds that act as inclusion hosts show quite different properties. One of these hosts forms a series of inclusion compounds with water, in which the site occupancy of the guest can range from 0-100% without change to the overall structure. All the X-ray structures described have been analysed in crystal engineering terms, and their supramolecular interactions described in detail.
| Identifer | oai:union.ndltd.org:ADTP/225418 |
| Date | January 2007 |
| Creators | Ashmore, Jason, Chemistry, Faculty of Science, UNSW |
| Source Sets | Australiasian Digital Theses Program |
| Language | English |
| Detected Language | English |
| Rights | http://unsworks.unsw.edu.au/copyright, http://unsworks.unsw.edu.au/copyright |
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