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研究生:張志豪
研究生(外文):Chih Hao Chang
論文名稱:一系列2-(4-烷苯基)6-甲氧基喹林液晶化合物之合成及相轉變之研究
論文名稱(外文):Synthesis and mesomorphic studies of a series of 2-(4-alkylphenyl)6-methoxyquinolines
指導教授:賈文隆賈文隆引用關係
指導教授(外文):Win-Long Chia
學位類別:碩士
校院名稱:輔仁大學
系所名稱:化學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2007
畢業學年度:95
語文別:中文
論文頁數:109
中文關鍵詞:一系列2-(4-烷苯基)6-甲氧基喹林液晶化合物之合成及相轉變之研究
外文關鍵詞:Synthesis and mesomorphic studies of a series of 2-(4-alkylphenyl)6-methoxyquinolines
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與商業用的5-CB比較,本實驗室以pyridine取代5-CB結構上的benzene合成了幾個具液晶相的compound,皆有不錯的成果,而此次研究試圖以6-methoxyquinoline取代pyridine的位置,試圖合成一系列2-(4-alkylphenyl)-6-methoxy quinoline(alkyl group為C4 to C8),首先將4-alkylbromobenzene與Mg混和,反應得到Grignard試劑;又將6-methoxy quinoline與氯甲酸苯酯混和,反應得到4-取代-甲氧基喹林鹽;再與Grignard試劑混和,反應得到一中間產物二氫喹林化合物。再將中間產物與氧化劑混和,進行氧化脫氫反應,可以得到產物2-(4-alkylphenyl)-6-methoxy quinoline。本次合成的化合物,產率約有50%~60%之間,而我們針對這些化合物將分別測定熱性質及觀察其相變化,試圖探討碳鏈長對液晶相的影響,並以1HNMR、13CNMR、IR測定其結構。
摘要.........................................................1
一、導論.....................................................3
1-1前言......................................................3
1-2液晶簡介..................................................8
1-2-1 液晶的由來.............................................8
1-2-2 液晶的結構.............................................9
1-2-3液晶的分類…………………………………………….......……10
1-2-4液晶相形成的條件.......................................12
1-2-5 液晶的觀察方法........................................12
二、文獻回顧……………………………………………………………...13
2-1 合成部分討論……………………………………...………...………13
2-2 研究動機…………………………………………………...………...20
三、原理……………………………………………………...……………22
3-1 3-取代-N-醯基吡啶鹽類………………………………......…………22
3-2格林那親核試劑…………………………………………...…………23
3-3 3-取代-N-醯基吡啶鹽類與格林那親核性試劑的反應...…...………24
四、實驗部份…………………………………………………...…………27
4-1 實驗藥品……………………………………………...……………...27
4-2 實驗儀器……………………………………………...…………….. 30
4-3 合成前的準備………………………………………………………..31
4-4 實驗步驟……………………………………………………………..33
4-3-1典型反應步驟與方法………………………………………………33
4-3-2氧化步驟……………………………………………………………36
4-3-3 實驗流程………………………………………...………………...36
4-4 再結晶的原理………………………………………………………..37
4-5 相轉移溫度測驗方法………………………………………………..39
4-6 液晶相種類的判別……………………………...………..………….40
五、結果與討論………………………………………..…………………47
5-1 合成部份的論:…………………..............................47
5-2 結構鑑定的份…………………………………………..……………49
5-2-1NMR的部份…………………………………………….…………..49
5-2-2 IR的部份………………………………………………….………..49
5-2-3 DSC的部份……………………………………………….………...50
5-2-4 POM觀察的部份……………………………………….………….52
5-2-5 EA部分…………………………………………………………….54
六、結論....................................................56
七、參考資料………………………………………………..…………...58
表目錄
Table 1 DSC(2nd Run)結果與數據…………………………...………...50
Table 2 EA送測結果與誤差.......................................54
Table 3 結果與數據(1H-NMR及13C-NMR)…………………...….…….61
Table 4結果與數據(mp及產率)……………………………...…….……62
Table 5 DSC(1st Run)結果與數據................................63
Table 6 DSC(2nd Run)結果與數據..................................64
Table 7液晶相種類及其溫度範圍...................................65
Table 8碳鏈長與溫度之相變化比較表(Heating).........................66
Table 9碳鏈長與溫度之相變化比較表(Cooling).........................67








圖目錄
Figure-1 起始物1-bromo-4-butylbenzene 之1H-NMR光譜.........68
Figure-2 起始物1-bromo-4-pentylbenzene 之1H-NMR光譜.........69
Figure-3 起始物1-bromo-4-hexylbenzene 之1H-NMR光譜.........70
Figure-4 起始物1-bromo-4-heptylbenzene 之1H-NMR光譜.........71
Figure-5 起始物1-bromo-4-octylbenzene 之1H-NMR光譜..........72
Figure-6 起始物6-methoxyquinoline 之1H-NMR光譜.............73
Figure-7 2-(4-butylphenyl)6-methoxyquinoline之1H-NMR光譜......74
Figure-8 2-(4-pentylphenyl)6-methoxyquinoline之1H-NMR光譜.....75
Figure-9 2-(4-hexylphenyl)6-methoxyquinoline之1H-NMR光譜......76
Figure-10 2-(4-heptylphenyl)6-methoxyquinoline之1H-NMR光譜....77
Figure-11 2-(4-octylphenyl)6-methoxyquinoline之1H-NMR光譜......78
Figure-12 起始物1-bromo-4-butylbenzene 之13C-NMR光譜........79
Figure-13 起始物1-bromo-4-pentylbenzene 之13C-NMR光譜.......80
Figure-14 起始物1-bromo-4-hexylbenzene 之13C-NMR光譜........81
Figure-15 起始物1-bromo-4-heptylbenzene 之13C-NMR光譜.......82
Figure-16 起始物1-bromo-4-octylbenzene 之13C-NMR光譜........83
Figure-17 起始物6-methoxyquinoline 之13C-NMR光譜............84
Figure-18 2-(4-butylphenyl)6-methoxyquinoline之13C-NMR光譜.....85
Figure-19 2-(4-pentylphenyl)6-methoxyquinoline之13C-NMR光譜....86
Figure-20 2-(4-hexylphenyl)6-methoxyquinoline之13C-NMR光譜....87
Figure-21 2-(4-heptylphenyl)6-methoxyquinoline之13C-NMR光譜....88
Figure-22 2-(4-octylphenyl)6-methoxyquinoline之13C-NMR光譜.....89
Figure-23 2-(4-butylphenyl)6-methoxyquinoline之DSC…………...……90
Figure-24 2-(4-pentylphenyl)6-methoxyquinoline之DSC……………….91
Figure-25 2-(4-hexylphenyl)6-methoxyquinoline之DSC……………..…92
Figure-26 2-(4-heptylphenyl)6-methoxyquinoline之DSC………….……93
Figure-27 2-(4-octylphenyl)6-methoxyquinoline之DSC…………..……94
Figure-28 2-(4-butylphenyl)6-methoxyquinoline之IR……………...…...95
Figure-29 2-(4-pentylphenyl)6-methoxyquinoline之IR…………..…......96
Figure-30 2-(4-hexylphenyl)6-methoxyquinoline之IR…………...….......97
Figure-31 2-(4heptylphenyl)6-methoxyquinoline之IR……………..........98
Figure-32 2-(4octylphenyl)6-methoxyquinoline之IR………....................99
Figure-33 2-(4-butylphenyl)6-methoxyquinoline之EA………….……..100
Figure-34 2-(4-pentylphenyl)6-methoxyquinoline之EA……….………101
Figure-35 2-(4-hexylphenyl)6-methoxyquinoline之EA…………….….102
Figure-36 2-(4-heptylphenyl)6-methoxyquinoline之EA……..….....…..103
Figure-37 2-(4-octylphenyl)6-methoxyquinoline之EA…………......….104
Figure-38 2-(4-butylphenyl)6-methoxyquinoline之 POM圖(cooling at86.9℃- x200)…………………………105
Figure-39 2-(4-pentylphenyl)6-methoxyquinoline之 POM圖(heating at 96.9℃- x400)…………………………106
Figure-40 2-(4-pentylphenyl)6-methoxyquinoline之 POM圖(cooling at 98.4℃- x200)…………………………106
Figure-41 2-(4-hexylphenyl)6-methoxyquinoline之 POM圖(cooling at 83.6℃- x400)………….……………107
Figure-42 2-(4-heptylphenyl)6-methoxyquinoline之 POM圖(heating at 94.0℃- x200)…………………………108
Figure-43 2-(4-heptylphenyl)6-methoxyquinoline之 POM圖(cooling at 94.8℃- x200)…………………………108
Figure-44 2-(4-octylphenyl)6-methoxyquinoline之 POM圖(cooling at 85.8℃- x20)…………………..………109











圖目錄
Figure-1 起始物1-bromo-4-butylbenzene 之1H-NMR光譜.........68
Figure-2 起始物1-bromo-4-pentylbenzene 之1H-NMR光譜.........69
Figure-3 起始物1-bromo-4-hexylbenzene 之1H-NMR光譜.........70
Figure-4 起始物1-bromo-4-heptylbenzene 之1H-NMR光譜.........71
Figure-5 起始物1-bromo-4-octylbenzene 之1H-NMR光譜..........72
Figure-6 起始物6-methoxyquinoline 之1H-NMR光譜.............73
Figure-7 2-(4-butylphenyl)6-methoxyquinoline之1H-NMR光譜......74
Figure-8 2-(4-pentylphenyl)6-methoxyquinoline之1H-NMR光譜.....75
Figure-9 2-(4-hexylphenyl)6-methoxyquinoline之1H-NMR光譜......76
Figure-10 2-(4-heptylphenyl)6-methoxyquinoline之1H-NMR光譜....77
Figure-11 2-(4-octylphenyl)6-methoxyquinoline之1H-NMR光譜......78
Figure-12 起始物1-bromo-4-butylbenzene 之13C-NMR光譜........79
Figure-13 起始物1-bromo-4-pentylbenzene 之13C-NMR光譜.......80
Figure-14 起始物1-bromo-4-hexylbenzene 之13C-NMR光譜........81
Figure-15 起始物1-bromo-4-heptylbenzene 之13C-NMR光譜.......82
Figure-16 起始物1-bromo-4-octylbenzene 之13C-NMR光譜........83
Figure-17 起始物6-methoxyquinoline 之13C-NMR光譜............84
Figure-18 2-(4-butylphenyl)6-methoxyquinoline之13C-NMR光譜.....85
Figure-19 2-(4-pentylphenyl)6-methoxyquinoline之13C-NMR光譜....86
Figure-20 2-(4-hexylphenyl)6-methoxyquinoline之13C-NMR光譜....87
Figure-21 2-(4-heptylphenyl)6-methoxyquinoline之13C-NMR光譜....88
Figure-22 2-(4-octylphenyl)6-methoxyquinoline之13C-NMR光譜.....89
Figure-23 2-(4-butylphenyl)6-methoxyquinoline之DSC…………...……90 Figure-24 2-(4-pentylphenyl)6-methoxyquinoline之DSC……………….91
Figure-25 2-(4-hexylphenyl)6-methoxyquinoline之DSC……………..…92
Figure-26 2-(4-heptylphenyl)6-methoxyquinoline之DSC………….……93
Figure-27 2-(4-octylphenyl)6-methoxyquinoline之DSC…………..……94
Figure-28 2-(4-butylphenyl)6-methoxyquinoline之IR……………...…...95
Figure-29 2-(4-pentylphenyl)6-methoxyquinoline之IR…………..…......96
Figure-30 2-(4-hexylphenyl)6-methoxyquinoline之IR…………...….......97
Figure-31 2-(4heptylphenyl)6-methoxyquinoline之IR……………..........98
Figure-32 2-(4octylphenyl)6-methoxyquinoline之IR………....................99
Figure-33 2-(4-butylphenyl)6-methoxyquinoline之EA………….……..100
Figure-34 2-(4-pentylphenyl)6-methoxyquinoline之EA……….………101
Figure-35 2-(4-hexylphenyl)6-methoxyquinoline之EA…………….….102
Figure-36 2-(4-heptylphenyl)6-methoxyquinoline之EA……..….....…..103
Figure-37 2-(4-octylphenyl)6-methoxyquinoline之EA…………......….104
Figure-38 2-(4-butylphenyl)6-methoxyquinoline之 POM圖(cooling at86.9℃- x200)………………………….…………………105
Figure-39 2-(4-pentylphenyl)6-methoxyquinoline之 POM圖(heating at 96.9℃- x400)………………………………..……………106
Figure-40 2-(4-pentylphenyl)6-methoxyquinoline之 POM圖(cooling at 98.4℃- x200)……………………………….……..……….106
Figure-41 2-(4-hexylphenyl)6-methoxyquinoline之 POM圖(cooling at
83.6℃- x400)………….…………………….……..………107
Figure-42 2-(4-heptylphenyl)6-methoxyquinoline之 POM圖(heating at 94.0℃- x200)…………………………………...………….108
Figure-43 2-(4-heptylphenyl)6-methoxyquinoline之 POM圖(cooling at 94.8℃- x200)……………………………..………………..108
Figure-44 2-(4-octylphenyl)6-methoxyquinoline之 POM圖(cooling at 85.8℃- x20)…………………..………………...………….109
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