鈀催化呋喃衍生物結構異構物的選擇性合成；
新型有機染料對於染料敏化太陽能電池

這篇論文分為兩個部分，在第一個部分中，我們知道benzofurans的衍生物存在於自然界中，而且具有許多的生物活性，如抗癌、抗病毒、抑制免疫、抗氧化、抗菌等等活性。所以在論文的第一部份我們想要探討的是利用1.Sonogashira coupling reaction 2.heterannulation這兩個步驟，使用Pd(II)這種過渡金屬當催化劑，在CuI當Co-catalyst以及amine base於有機溶劑的環境下，使用兩種相同的起始物，2-iodophenol以及Methyl 3-butynoate去催化合成benzofuran 的衍生物。在固定的反應條件下，僅改變 Co-catalyst ( CuI )的當量數，可以選擇性的得到兩種不同的產物；二號位置或三號位置上有取代的benzofuran。或許可以藉由此方式來幫助研究有關於benzofuran衍生物先導藥物的開發。由於社會的發展，人們對石油的需求越來越大。但是石化燃料終會耗竭，並帶來空氣污染。所以發展乾淨、應用範圍廣、取之不盡、用之不竭的替代能源為當務之急。所以在本論文的第二部分主要討論染料敏化太陽能電池(dye-sensitized solar cells, DSSCs)之染料部分，至目前為止，具備較高效能的染料敏化太陽能電池其成本仍然過高，因此為了降低成本而發展出以有機染料為主的染料敏化太陽能電池。我們計劃開發新型的有機染料。對已知的染料稍做改變，使染料能運用於敏化太陽能電池。化合物 chromeno[3’,2’:3,4]pyrido[1,2a][1,3]benzimidazole chromophore為一種已知的偏長波長染料，其合成方式可由兩步得到。到目前為止並未有以該化合物作為敏化劑的敏化太陽能電池。因此本計畫以該染料為設計模版，在模板上接上carboxylic acid官能基使染料能緊密吸附在TiO2上。

關鍵字

呋喃；選擇性異構物合成；碳-碳偶合；鈀催化染料敏化太陽能電池；有機染料；釕錯合物；二氧化鈦

並列摘要

This thesis consists of two parts. In the first part, as we known Benzo[b]furans are of considerable interest due to their occurrence in nature as well as their biological activities, such as anticancer、antiviral、immunosup-pressive、antioxidant、antifungal. So in the first part of the thesis, we want to investigate that benzo[b]furans accomplished in two steps：1.Sonogashira coupling reaction 2.heterannulation. The reaction is performed with a palladium catalyst, a copper(I) cocatalyst, and an amine base in organic solvent. Using the same compounds; 2-iodophenol and Methyl 3-butynoate to synthesis benzofuran derivatives. In the same reaction condition, we only change the equivalent of CuI that we can get two different compounds, 2 or 3 substitutedbenzofuran derivatives. We can get some help about the investigation of benzofuran derivatives Drug Lead in this way. The change of mankind's life with the development of the technology and becomes more convenience and comfortable. It also makes us to need more energy. So it is very important to develop the new energy. In the second part of this thesis mainly discusses the dyestuffs part of the dye-sensitized solar cell. To date the cost of the highest efficiency of the dye-sensitized solar cell is still too high. Therefore , In order to lower costs, we developed dye-sensitized solar cell based on organic dyes. We plan to develop the new-type organic dyes. We try to modify the known dyestuffs slightly, enable dyestuffs to apply to the dye-sensitized solar cell. The known compound chromeno[3’,2’:3,4]pyrido[1,2a][1,3]benzimidazole chromophore was a relatively long-wavelength fluorophore and easily prepared in two steps. Up till now this chemical compound has not been used on the dye-sensitized solar cell. We will incorporate a carboxylic-acid group in this compound to make sure it can bind strongly to TiO2.

並列關鍵字

benzofuran ； Regioisomer synthesis ； C-C coupling ； Palladium catalysis ； dye-sensitized solar cell ； organic dyes ； Ruthenium complexes ； TiO2

參考文獻

[1]. K. C. Nicolaou, Scott A. Snyder, Tamsyn Montagnon, and Georgios Vassilikogiannakis. “The Diels-Alder Reaction in Total Synthesis,” Angew. Chem. Int. Ed, 41, pp.1668-1698, 2002.

[2]. F. A. Bottino, G. Di Pasquale, A. Pollicino, Antonino Recca, and D. T. Clark. “Synthesis of 2-(2-hydroxyphenyl)-2H-benzotriazole monomers and studies of the surface photostabilization of the related copolymers,” Macromolecules, 23, pp.2662-2666, 1990

[3]. Lai. Y-H. , "Grignard Reagents from Chemically Activated Magnesium," Synthesis, 8, pp.585-604, 1981.

[4]. K. C. Nicolaou, Paul G. Bulger, and David Sarlah, “Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis,” Angew. Chem. Int. Ed, 44, pp.4442–4489, 2005.

[5]. Alec D. Lebsack, J. T. Link, Larry E. Overman, and Brian A. Stearns, “Enantioselective Total Synthesis of Quadrigemine C and Psycholeine,” J. Am. Chem. Soc, 124 , pp.9008-9009, 2002.

國際替代計量

鈀催化呋喃衍生物結構異構物的選擇性合成；新型有機染料對於染料敏化太陽能電池

未授權

主題瀏覽