本篇論文分為合成與應用兩章節，第一章為基礎合成部分，一般缺電子芳香環的耦合反應需要先經過活化後再與金屬試劑進行反應，而在本篇論文中使用新合成方法，以Phenyliodine diacetate (PIDA)作為反應試劑，此合成方式環保且有效率，不需經過活化及使用金屬試劑即可一步進行缺電子芳香環吡啶之耦合反應。
第二章則是將前篇得到之3,3’-dihydroxy-2,2’-bipyridine合成一系列的化合物應用在液晶領域上，並以偏光顯微鏡、微差掃描卡計和X光粉末繞射儀做性質的分析，我們假設化合物a-3可能具有具有立方結構相，且對稱性為Im3m，系列二化合物d-1~d-3產生之中間相可能為層形排列。

The thesis can be divided into two chapters: synthesis and application. The first chapter presents the basis of synthesis. Generally, electronic-deficient aromatic molecules require activation before reacting with metal reagents and then can go coupling reaction. Our lab has developed a new bipyridine coupling method without pre-functionalization of pyridines to the corresponding activated halide or metal forms or using of transition metal catalysts. This new method is quite efficient and advantageous for environmental protection.

In second chapter, we synthesized 3,3’-dihydroxy-2,2’-bipyridine -based molecules and the functional groups were modified to investigate its liquid crystal properties. According to analyzing data of differential scanning calorimetry (DSC), polarized optical microscope (POM) and powder x-ray diffraction (XRD), we found that a-3 may possess cubic mesophaes with Im3m symmetry, and a series of d-1~d-3 compounds exhibit mesophase and may be further identified as smectic phase.

論文審定書 i
誌謝 ii
中文摘要 iii
英文摘要 iv
目錄 v
圖目錄 viii
表目錄 xii
流程目錄 xiii
1 合成部分 1
1-1 缺電子芳香環與高價碘試劑之反應 1
1-1.1 多電子芳香環與高價碘試劑的耦合反應 1
1-1.2 研究動機 7
1-1.3 結果與討論 9
1-1.4 結論 14
1-1.5 實驗步驟 15
1-2 3,3’-dihydroxy-2,2’-bipyridine的合成 17
1-2.1 化合物介紹 17
1-2.1.1 化合物之應用 17
1-2.1.2 合成文獻回顧 23
1-2.2 研究動機 28
1-2.3 實驗結果與討論 29
1-2.4 結論 33
1-2.5 實驗步驟 35
2 應用部分 36
2.1 緒論 36
2.1.1 液晶基本構造 36
2.1.2 液晶分類 37
2.1.3 文獻回顧 43
2.1.3.1 具有2,2’-bipyridine結構之液晶 43
2.1.3.2 具相似構型之液晶 46
2.2 實驗原理及液晶相鑑定 49
2.2.1 偏光顯微鏡的原理(Polarizing Microscope, POM) 49
2.2.2 微差掃描熱卡計(Differential Scanning Calorimetry, DSC) 50
2.2.3 X光粉末繞射(Powder X-ray Diffraction, XRD) 52
2.3 合成部分 55
2.3.1 研究動機與目的 55
2.3.2 合成策略 56
2.3.3 實驗流程與討論 58
2.4 液晶相鑑定及探討 62
2.4.1 phenyl系列ㄧ之液晶相鑑定與探討 62
2.4.2 biphenyl系列二之液晶相鑑定與探討 66
2.5 結論 74
2.6 實驗儀器及藥品 75
2.7 實驗步驟 77
3 參考文獻 105

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