1. Synthesis of the Heterocyclic Natural Products and the Skeletons: Application of Organotungsten Chemistry.2. Synthesis and Characterization of the Novel Organic Light-Emitting Diode (OLED) Materials.

• Main Authors: Heh Lung Huang, 黃賀隆
• Other Authors: Rai Shung Liu
• Format: Others
• Language: en_US
• Published: 2003
• Online Access: http://ndltd.ncl.edu.tw/handle/71750397150840640163

博士 === 國立清華大學 === 化學系 === 91 === The dissertation discusses several new tungsten- and iridium-mediated reactions and their applications. This dissertation has three chapters. The first two chapters elucidate tungsten-mediated cyclizations and the third chapter addresses the synthesis of organic materials used as light-emitting diodes (OLEDs). The first chapter establishes a short and easy route for synthesizing naturally occurring bicyclic alkaloids－(±)-lupinine, (±)-epilupinine, and (±)-laburnine, via the intramolecular cyclization of alkynyltungsten compounds with N-acyliminium ions. Using this method, a common synthetic route for constructing the bicyclic lactam derivatives is determined. The second chapter establishes a short and effective route for synthesizing chiral tricyclic furanyl and pyranyl derivatives via tungsten-mediated cycloalkenation. The chiral endocyclic dienes are synthesized using the chiral dioxolane group as a chiral auxiliary and they further undergo diastereoselective Diels-Alder reactions to produce tricyclic furanyl and pyranyl cycloadducts. The chiral dioxolane substituents of the cycloadducts were degraded to cause these molecules to have common furanyl and pyranyl rings. In the third chapter, some OLED materials, including fluorescent and phosphorescent materials, are synthesized. The organic blue emissive fluorescent materials are characterized by the ease of their preparation, thermal stability and high brightness. The orange to red emissive organo-iridium complex as a phosphorescent material is easily prepared and has moderate luminance.