Chemistry of acenes: syntheses, characterizations and reactions.

• Other Authors: Wang, Yuman.
• Format: Others
• Language: English; Chinese
• Published: 2007
• Subjects: Organic compounds > Synthesis
• Online Access: http://library.cuhk.edu.hk/record=b6074519; http://repository.lib.cuhk.edu.hk/en/item/cuhk-344152

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.