我們利用威惕反應快速且簡便地合成出以二苯并[a,c]蒽為核心架構的盤型分子，並對其引入長度不同的側鏈基以改變分子的對稱性，再藉由偏光顯微鏡、微差掃描熱卡計以及X光粉末繞射儀對此系列分子進行鑑定，發現到此系列的化合物均不具有液晶性質，而其中某些化合物會產生球晶狀排列。我們亦從威惕反應中得到一未知結構的化合物，其經鑑定後具有六角塑性管柱堆疊的液晶性質。此外，我們也嘗試合成以二苯并[f,h]吡嗪并[2,3-b]喹喔啉為盤狀核心的液晶分子，欲明白盤狀核心之偶極矩對於液晶性質的影響，可是肇因於合成上的困難，最終並未達成目標。

We have synthesized the Dibenz[a,c]anthracene as the discogen via Wittig reaction with simply and quickly routes. Otherwise, We adjusted the molecule symmetry with modifying the alkoxy side-chain length. The properties of the series of compounds which based on Dibenz[a,c]anthracene as discogens were determined through polarized optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD). Finally, we found that all series were not exhibiting liquid crystal properties but some of them showing the spherulite alignment. We also obtained a series of compounds with unknown structure accidentally via Wittig reaction. Some of them exhibited liquid crystal properties with hexagonal plastic columnar phase. On the other hand, we were still curious about the effect upon enhancing dipole moment of the core. So, we attempted to synthesize Dibenzo[f,h]pyrazino[2,3-b]quinoxaline as the discogen. Unfotunately, we finally failed with difficulties in the synthesis procedure.

論文審定書 i
謝誌 ii
中文摘要 iv
英文摘要 v
目錄 vi
圖目錄 ix
表目錄 xiii

第一章 緒論 1
1-1 前言 1
1-2 液晶簡介 2
1-3 盤狀液晶 8
1-4 盤狀液晶之論文回顧 13
1-4.1 盤狀液晶的組成概述 13
1-4.2 不對稱盤狀液晶 15
1-5 非盤狀分子之盤狀液晶 23
第二章 實驗部分 28
2-1 研究動機 28
2-2 合成策略 28
2-3 合成方法探討 31
2-3.1 合成對稱的威悌反應前驅物 31
2-3.2 合成不對稱的威悌反應前驅物 32
2-3.3 合成Tetraalkoxyphenanthrene-9,10-dione 34
2-3.4 合成Dibenz[a,c]anthracene 37
第三章 結果與討論 39
3-1 檢測與分析 39
3-2 物理性質的探討 44
3-2.1 系列一 （Mono-functionalized System） 45
3-2.2 系列二 （Di-functionalized System） 51
3-2.3 系列一－綜合比較 72
3-2.4 系列二－綜合比較 75
3-2.5 系列三 （Tri-functionalized System） 79
3-2.6 系列四 （Unknown Compounds via Wittig rxn） 88
第四章 合成Dibenzo[f,h]pyrazino [2,3-b]quinoxaline盤狀核心 102
4-1 研究動機 102
4-2 合成策略 102
4-3 結果與討論 103
第五章 結論 113
第六章 實驗步驟 117
參考文獻 154
附錄 157
一、 微差掃描熱卡計檢測結果 157
二、 未知化合物X-PC10DC8之一維與二維光譜 172

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