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研究生： 潘欣怡
Hsin-yi Pan
論文名稱： 4,5-烷基-吩系列衍生物之合成及性質探討
Synthesis and Characterization of 4,5-alkyl groups thiophenes Derivatives
指導教授： 王英靖
Ing-Jing Wang
口試委員: 陳耿明
Keng-Ming Chen
郭中豐
Chung-Feng Jeffrey Kuo
學位類別： 碩士
Master
系所名稱： 工程學院 - 材料科學與工程系
Department of Materials Science and Engineering
論文出版年： 2007
畢業學年度： 95
語文別： 中文
論文頁數： 74
中文關鍵詞： 偶氮基 、氮次甲基
外文關鍵詞： 3-cyanothiophenes, azo-methine, azo
相關次數： 點閱：211  下載：1 
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    • 本研究旨在以硫粉(Sulfur)、丙二(Malononitrile)及脂肪酮(Aliphatic ketone)合成不同的4,5-二取代-2-胺基-3-基吩[4,5-disubstituted 2-amino-3-cyanothiophenes](4a~4c)中間體，再與4-取代基-苯醛(5a~5c)在鹼性觸媒存在下縮合成具有氮次甲基azo-methine(C=N)發色團的3-基吩氮次甲基染料(6a-6i)，再將4,5-二取代-2-胺基-3-基吩[4,5-disubstituted 2-amino-3-cyanothiophenes](4a、4b)中間體當重氮鹽與4-取代基-苯環(7a~7b)在冰浴下偶合成具有偶氮基azo(N=N)發色團的3-基吩偶氮染料(8a~8d)。進而將合成的吩染料，分別在不同的溶劑下測定其紫外/可見光吸收光譜，探討不同極性對最大吸收波長之影響。所合成之化合物均經（UV、FT-IR、1H-NMR、MS）等光譜鑑定確定其化學構造。

    In this study, different [4,5-disubstituted 2-amino-3-cyanothiophenes] (4a~4c) intermediates have been synthesized by reaction of Sulfur、Malononitrile and Aliphatic ketone. Then, the 4a~4c compounds were condensed with 4-substituted-benzaldehyde in the presence of catalytic amount of piperidine to get the 3-cyanothiophene azomethine dyes(6a~6i) which contain azomethine (C=N) chromophor. Moreover, the 3-cyanothiophene azo dyes(8a~8d) which contain azo chromophor (N=N) were synthesized by 4a and 4c azo compounds coupling reaction with the 4-substituted-benzene in ice bath. The solvatochromic behavior of these thiophene dyes in various solvents was evaluated. The structures of these compounds were determined by spectrometry (UV、FT-IR、1H-NMR、MS).

    中文摘要I ABSTRACTII 誌 謝III 目錄V 圖表目錄VII 第1章前言1 第2章實驗3 2.1實驗材料3 2.2實驗儀器5 2.3合成方法6 2.3.14,5-二取代-2-胺基-3-基吩(4,5-disubstituted-2-amino-3-cyanothiophenes)(4a-4c)之合成………6 2.3.2雜環染料(heterocyclic dyes) (6a-6i)之合成8 2.3.3雜環單偶氮染料(heterocyclic monoazo dyes) (8a-8d)之合成.12 2.4紫外線-可見光吸收光譜測定(UV)16 2.5熔點測試17 2.6紅外線吸收光譜測試17 第3章結果與討論18 3.1化合物(4a~4c)的合成及光譜分析18 3.1.1化合物(4a-4c)之合成18 3.1.2化合物(4a-4c)的物理實驗數據及光譜數據分析22 3.2雜環染料(Heterocyclic dyes)(6a-6i)之合成及光譜分析25 3.2.1化合物(6a-6i)之合成25 3.2.2化合物(6a~6i)的物理實驗數據及光譜數據分析26 3.2.2.1化合物(6a~6i)的光譜數據分析34 3.3雜環單偶氮染料(Heterocyclic monoazo dyes)(8a-8d)之合成及光譜分析37 3.3.1化合物(8a-8d)之合成37 3.3.2化合物(8a-8d)的物理實驗數據及光譜數據分析39 3.3.2.1化合物(8a~8d)的光譜數據分析43 第4章結論45 參考文獻47 作者簡介........................................................................................................74

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