本論文中的最終產物是藉由本實驗室已開發的的1,2雙酮化合物經由縮合、酸化及酯化反應所得到，主要目的是希望利用快速且簡便的方式，合成出以二氮三亞苯為核心架構，並引入酯基為柔軟側鏈的盤狀液晶分子，透過偏光顯微鏡、微差掃描卡計和X光粉末繞射儀鑑定此系列化合物液晶相的物理性質。研究結果發現二氮三亞苯雙酯基化合物其展現優於過去三亞苯衍生物的液晶相性值，並在降溫過程時有過冷現象的發生，在室溫下以塑晶的形式呈現，證實酯基官能基能夠有效提升中間相的穩定度，使液晶相範圍大幅提升，最後針對系列化合物具有不同長度的柔軟側鏈進行測定，證實化合物在液晶相時是以反向方式進行排列。

The diazatriphenylene discotic liquid crystals with dicarboxylic ester peripheral side-chains were readily synthesized through the following sequence of reactions:
(i) condensation of 2,3-diaminomaleonitrile with tetraalkoxyphenanthrene-9,10-dione, (ii) hydrolysis of nitrile to carboxylic acid and (iii) esterification with alkanol. Most of these compounds were found to exhibit mesogenic properties as determined by polarized optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD). In our investigations we observed that the carboxylic ester showed improve mesogenic properties as compare to the triphenylene counterpart, and on cooling to room temperature formed plastic phase readily. We also synthesized compounds having different peripheral chain length of the ester to demonstrate that the antiparallel packing of the discogen in this series of discotic liquid crystals.

審定書 i
謝致 ii
中文摘要 iii
Abstract iv
目錄 v
圖目錄 viii
表目錄 xi
第一章緒論 1
1-1前言 1
1-2液晶簡介 2
1-3液晶的分類 3
1-3-1液晶相形成的方式 3
1-3-2分子量的大小 4
1-3-3液晶元的不同 4
1-4盤狀液晶分子特色 9
1-5 Triphenylene盤狀液晶分子文獻回顧 10
1-5-1酯基對盤狀液晶分子的影響 14
第二章實驗部分 20
2-1研究動機 20
2-2合成策略 21
2-3實驗流程與討論 22
2-3-1烷化（alkylation） 22
2-3-2 Friedel-Crafts acylation 22
2-3-3 環化（cyclization） 23
2-3-4縮合（condensation） 24
2-3-5酯化（Esterification） 25
第三章物性檢測與探討 26
3-1 系列一 26
3-1-1系列一之POM觀測 27
3-1-2系列一之DSC檢測 29
3-1-3系列一XRD測量 31
3-1-4系列一之綜合討論 35
3-2系列二 38
3-2-1系列二之POM觀測 39
3-2-2系列二之DSC檢測 42
3-2-3系列二之XRD檢測 45
3-2-4系列二之綜合討論 49
3-3系列三 51
3-3-1系列三之POM觀測 52
3-3-2系列三之DSC檢測 54
3-3-3系列三之XRD測量 55
3-1-4系列三之結論 57
第四章總結論 58
第五章 實驗部分 60
儀器設備 60
藥品與溶劑 61
過程 61
化合物合成條件與檢測資料 62
1,2-Bis(alkoxy)benzene [20] (1) 62
3,3', 4,4'­Tetrakisalkoxybenzil [21] (2) 64
2,3,6,7-Tetrakis(alkoxy) phenathrene-9,10-dione[21] (3) 66
2,3-dicyano-6,7,10,11-tetraalkoxy-1,4-diazatriphenylene[13] (4) 68
2,3-dicarboxylic acid-6,7,10,11-tetraalkoxy-1,4-diazatriphenylene [23] (5) 70
2,3-dicarboxylic ester-6,7,10,11-tetraalkoxy-1,4-diazatriphenylene [23] (6) 71
參考文獻 75
附錄 77

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