Wang, Mingdong. / Thesis (Ph.D.)--Chinese University of Hong Kong, 2011. / Includes bibliographical references. / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstract also in Chinese.

Thesis (Ph. D.)--University of Hong Kong, 2007. / Title proper from title frame. Also available in printed format.

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Field effect transistors (FETs) are a key component of modern electronic devices. They require a semiconducting material that is traditionally made from doped silicon. Recently however it has been shown that porphyrin systems can be used in the same capacity. This thesis therefore describes the investigation of new methods of porphyrin functionalization to synthesise 1,4,5,8-tetraazaanthracene-bridged porphyrin arrays, and their application to the synthesis of extended arrays for use in FETs. The 1,4,5,8- tetraazaanthracene bridge is synthesised through the condensation of a porphyrin alpha-dione with 1,2,4,5-tetraaminobenzene. Accordingly, the synthesis of an extended array requires a porphyrin tetra-one monomer unit. Two methods for the synthesis of porphyrin tetra-ones have been investigated. The first approach attempts to adapt Knudsen's hydroxylation of an aryl halide by sodium benzaldoximate to a porphyrin system. Initial regiospecific halogenation of a porphyrin has been successfully achieved. However when hydroxylation was attempted, partial dehalogenation of the substrate was observed; and when applied to the synthesis of the porphyrin tetra-one the methodology failed. The second approach involves the allylic oxidation of a chlorin (a reduced porphyrin) on silica. The transformation's mechanism has been thoroughly investigated and it has been successfully applied to the synthesis of a porphyrin tetra-one. This methodology has then been applied to the synthesis of extended porphyrin arrays. A sample incorporating 12 porphyrin units has been successfully constructed. It has been characterised by NMR, MALDI, GPC and UV-VIS spectroscopy. By comparison with previous results it has been concluded that the aromatic system- which spans 181 Ǻngstroms from end to end- can be described as a series of weakly interacting chromophores, in agreement with theoretical predictions made by Hush. In addition a medium-scale synthesis of an array incorporating four porphyrins has been achieved so that it may now be tested as the semiconducting material in a FET.

Polymer based photovoltaic cells are being intensively investigated. In such cells three key processes need to occur; namely light absorption, charge separation of the exciton, and transport of the separated charges to the electrodes. Light absorption is reliant on the optical density of the polymer. In general charge separation is achieved by blending an electron acceptor with the polymer film. However, blending materials gives rise to potentially unreliable manufacturing and lifetime issues. This thesis describes the preparation of poly(l,4-phenylenevinylene) derivatives containing dipoles in which the process of charge separation can be achieved intramolecularly. The dipole was created with the use of electron donating alkoxy groups attached to the polymer backbone, and electron withdrawing nitro group attached to the fluorenyl side chains. These groups are believed to facilitate the dissociation of the photogenerated exciton, and potentially stabilise the holes and electrons that are formed when the exciton is separated. The fluorenyl side chains were attached to the polymer backbone via biphenyl or vinyl linkages. The polymers were primarily formed using the Gilch method and the conjugated polymers were obtained either via a soluble precursor route or directly from the monomer. The photophysical properties were studied for polymers with the fluorenyl side-chains as they were found to be more easily formed and stable. For poly[2-(7-nitro-9,9-dipropylfluorenyl)-5-(2'- ethylhexyloxy)-l,4-phenylenevinylene] it was found that the photoluminescence quantum yield dropped by a factor of eight relative to the polymer without the nitro group. It was further elucidated that this was due to the exciton being separated. Solar cells containing the polymers from this study showed modest performance.

Thesis (M.S.)--Brigham Young University. Dept. of Chemistry and Biochemistry, 2006. / Includes bibliographical references.

Thesis (M.M.S.E.)--University of Delaware, 2008. / Principal faculty advisor: Valeria Gabriela Stoleru, Dept. of Materials Science & Engineering. Includes bibliographical references.