2,3,9,10-Tetrakis(trimethylsilyl)pentacene (169) and a series of its derivatives were synthesized. In addition, their structures, physical properties and reactions were fully studied. Longer substituted heptacenequinone 219 was synthesized and used to synthesize the heptacene derivative. / Chapter 2 concerns the aim of our research work and strategy. Soluble 2,3,9,10-tetrakis(trimethylsilyl)pentacene (169) and its deriva- tives 171-182, bulky o-carboranyl substituted pentacene derivative 190 and 6-chloro-2,3,9,10-tetrakis(trimethylsilyl)pentacene (192 ) were successfully synthesized. In addition, Diels-Alder reactions of 2,3,9,10- tetrakis(trimethylsilyl)pentacene (169) and 6-chloro-2,3,9,10-tetrakis- (trimethylsilyl)pentacene (192) with different dienophiles were carried out. Sterically hindered and unreactive 6-chloro-2,3,9,10-tetrakis(trimethylsilyl)pentacene (192) underwent coupling reaction with Grignard reagent in the presence of a nickel complex affording coupling product 208 and pentacene dimer 209 as a Wurtz-like coupled product. In addition, 2,3,11,12-tetrakis(trimethylsilyl)-7,16-bis(trimethylsilylethynyl)heptacene (220) was found to dimerize very readily with a head-to-tail structure confirmed by an X-ray diffraction study. / Chapter 4 is the experimental section. / In Chapter 1, a brief introduction of properties, applications, syntheses and reactions of pentacene is given. In addition, the chemistry of heptacene is also presented. / In Chapter 3, a brief conclusion is provided. / Wang, Yuman. / "September 2007." / Source: Dissertation Abstracts International, Volume: 69-08, Section: B, page: 4765. / Thesis (Ph.D.)--Chinese University of Hong Kong, 2007. / Includes bibliographical references (p. 128-147). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Electronic reproduction. [Ann Arbor, MI] : ProQuest Information and Learning, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstracts in English and Chinese. / School code: 1307.
| Identifer | oai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_344152 |
| Date | January 2007 |
| Contributors | Wang, Yuman., Chinese University of Hong Kong Graduate School. Division of Chemistry. |
| Source Sets | The Chinese University of Hong Kong |
| Language | English, Chinese |
| Detected Language | English |
| Type | Text, theses |
| Format | electronic resource, microform, microfiche, 1 online resource (v, 231 p. : ill.) |
| Rights | Use of this resource is governed by the terms and conditions of the Creative Commons “Attribution-NonCommercial-NoDerivatives 4.0 International” License (http://creativecommons.org/licenses/by-nc-nd/4.0/) |
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