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  • 學位論文

2-芳香族取代吡啶的合成研究

Research on the synthesis of 2-aryl pyridines

指導教授 : 李世元

摘要


2-芳香基吡啶衍生化合物在生活中被廣泛運用,像是藥物治療上與材料上的應用。材料廣泛應用在染敏化太陽能電池和有機發光二極體上。目前合成雙芳香族化合物反應多會添加過度金屬試劑作為催化劑,使反應更容易進行。然而吡啶上的氮孤對電子沒有參與環內共振,所以可以作為配位基和金屬配位,可能抑制過度金屬催化劑,而另一反應芳香族可能因此產生自我耦合反應。為了避免發生此現象,本實驗決定採取最基本的反應型式,即是親核芳香取代反應,且為了使實驗操作方便,採取巴比艾爾反應來找出最佳反應條件,除了操作上簡便且更符合綠色化學。

並列摘要


2-Aryl pyridines are widely used in our lives as medicines or materials. 2-Aryl pyridines are often applied electro-optical material such as DSSC and OLED. Synthesis 2-aryl pyridines, transition metal as catalyst usually was added to pursue the reaction proceed easily. However, the lone pair on nitrogen atom of pyridine does not delocalized in aromatic resonance, so it could behave as ligand to coordinate with metals, which might produce self-coupling compound faster than the expected hetero-coupling product. To avoid this homocoupling side reaction we use the reaction such as the aromatic nucleophilic substitution reaction for synthesis of 2- aryl pyridines. Therefore, we chose Barbier-type reaction to disclose the best reaction conditions for synthesizing 2-aryl pyridines, this method not only simplify the conducting procedures, but also more eco friendly.

參考文獻


[1] Tokito, S. Appl. Phys. Lett. 2003, 83, 569.
[2] Holmes, R. J.; D’Andrade, B. W.; Forrest, S. R. Appl. Phys. Lett. 2003, 83, 3818.
[3] S.‐J. Yeh M.‐F. Wu C.‐T. Chen. Adv. Mater.2004,01,373
[4] Tsuzuki, T.; Shirasawa, N.; Suzuki, T.; Tokito, S. Adv. Mater. 2003, 15, 1455.
[5] Adachi, C.; Baldo, M. A.; Forrest , S. R. Appl. Phys. Lett. 2001, 78, 1622.

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