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研究生:王翔正
研究生(外文):Hsiang-cheng Wang
論文名稱:具有benzoxazole結構之有機及無機液晶材料
指導教授:賴重光賴重光引用關係
指導教授(外文):Chung-Kung Lai
學位類別:碩士
校院名稱:國立中央大學
系所名稱:化學研究所
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:2005
畢業學年度:93
語文別:中文
論文頁數:223
中文關鍵詞:液晶
外文關鍵詞:benzoxazoleliquid cyrstal
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本篇論文包含兩種具有benzoxazole結構之有機及無機液晶。
系列一為具有萘環及benzoxazole結構之無機液晶,此系列以化合物2 ( 6-alkoxynaphthalene-2-carboxylic acid 4-(6-alkoxybenzooxazol- 2-yl)-3-hydroxyphenyl ester )為配位基,與過渡金屬銅及鈀配位形成無機液晶,所得之化合物皆以1H、13C-NMR及元素分析鑑定,並以DSC、偏光顯微鏡及POWDER X-RAY鑑定其液晶相。
此系列配位基皆具有N相,碳鏈長度大於6 (n = 6 ~ 12)時出現SmC相,銅錯合物亦都具有N相,碳鏈長度為12時才出現SmC相;鈀錯合物僅短碳鏈(n = 1,4)時才出現N相。二價銅離子與鈀離子皆為平面四邊形配位,造成此現象的原因應與金屬離子與配位基之間鍵長的差異有關。此系列化合物皆有化合物單晶結構,並亦對配位基及錯合物做螢光發光測試。
系列二為具有兩個benzoxazole結構之有機分子,並分別做了碳鏈長度(n = 6 ~ 16)與碳鏈根數(R = 2 ~ 6)的變化,希望能得到盤狀及桿形的分子結構,並形成液晶相,但是由DSC及偏光顯微鏡鑑定之後發現所有化合物皆為結晶相,顯示分子間吸引力大於碳鏈擾動的能力,無論碳鏈根數多寡及碳鏈長度,皆無法形成液晶相。另外亦對此系列化合物做螢光發光測試,討論側鏈根數及位置對發光效率的影響。
In this thesis, we report the synthesis, characterization and mesomorphic properties of two novel series of new mesogenic derivatives based on benzoxazole structure.
In serie one , this synthesis, characterization, and mesomorphic properties of a new type of transition metal complexes 1a-1b derived from benzoxazoles 2 as core group are reported. These metal complexes were obtained by the reactions of 6-alkoxynaphthalene-2-carboxylic acid and 4-(6-dodecyloxy benzooxazol-2-yl)-3-hydroxyphenyl esters. The metal complexes were obtained by reaction of benzoxazoles 2 and copper (II) or palladium acetate in refluxing ethanol. All compounds were characterized by 1H, 13C-NMR spectroscopy and elemental analysis. The phase behavior of these mesogenic compounds was characterized and studied by differential scanning calorimeter (DSC) and polarization optical microscope.
All compounds with shorter chains (n = 0, 1, 4, 6, 7, 8, 10, 12) exhibited nematic (N) and/or smectic C (SmC) phases, as expected for rod-like molecules. For copper(II) compounds 1a with shorter chains (n = 0, 1, 4, 6, 7, 8, 10) nematic phase was observed only, whereas those compounds having longer carbon chains (n = 12) smectic C phase was also observed at lower temperatures. However, palladium(II) complexes formed nematic phases with short chains (n = 1, 4) only. The difference in the mesomorphic properties observed by compounds 1a and 1b was probably attributed to the geometry at the metal center. Although the Cu2+ ions and Pd2+ ions are both square planar geometries, but the difference of bond length between metal center and ligand is the major effect of mesomorphic behavior. The fluorescent properties of these compounds were also examined.
In serie two,we designed and characterized a series of new type of organic molecule 3 ~ 6 derived from two benzoxazoles with two to six side chains. These compounds were prepared by the ring closure reaction of 4,4'-Bis[(3,4,5-trialkoxybenzylidene)amino]biphenyl-3,3'-diol in the presence of lead(Ⅳ) acetate. All compounds were characterized by 1H, 13C-NMR spectroscopy and elemental analysis. The phase behavior of these mesogenic compounds was characterized and studied by differential scanning calorimeter (DSC) and polarization optical microscope.
All compounds with two(n = 16) to six side chain(n = 6 ~ 16) exhibited crystal phase, indicate that the interaction between molecules are more larger than the side chain flexibility, no matter how many side chain does the molecule have. The fluorescent properties of these compounds were also examined.
中文摘要……………………………………………………………………Ⅰ
英文摘要……………………………………………………………………Ⅱ
謝誌…………………………………………………………………………Ⅳ
目錄…………………………………………………………………………Ⅵ
圖目錄……………………………………………………………………ⅩⅠ
表目錄……………………………………………………………………ⅩⅤ
附圖目錄…………………………………………………………………ⅩⅥ
第一章 緒論………………………………………………………………1
1-1 前言………………………………………………………………2
1-2 液晶分子的構造與物理性質……………………………………3
1-3 液晶的分類………………………………………………………5
1-4 包含發光基團的桿狀液晶材料的研究及應用…………………11
1-5 盤狀液晶材料的研究及應用……………………………………14
1-6 研究動機…………………………………………………………19
第二章 實驗部分…………………………………………………………21
2-1 實驗藥品…………………………………………………………22
2-2 實驗儀器設備……………………………………………………23
2-3 實驗流程…………………………………………………………29
2-3-1 系列一之實驗流程………………………………………………29
2-3-2 系列二之實驗流程………………………………………………30
2-4 實驗步驟…………………………………………………………31
2-4-1 Bis[6-alkoxynaphthalene-2-carboxylic acid 4-(6-dodecyl oxybenzooxazol- 2-yl)-3-hydroxyphenyl ester] metal 系列之合成……………………………31
2-4-1-1 6-Alkoxynaphthalene-2-carboxylic acid之合成………………………………31
2-4-1-2 6-Alkoxynaphthalene-2-carboxylic acid 4-formyl-3- hydroxyphenyl ester
之合成……………………………………………………………………………… 32
2-4-1-3 3-Alkyloxyphenol之合成………………………………………………………… 37
2-4-1-4 5-Alkyloxy-2-nitrophenol之合成……………………………………………… 38
2-4-1-5 2-Amino-5-alkyloxyphenol之合成.………………………………………………39
2-4-1-6 6-Alkoxynaphthalene-2-carboxylicacid4-[(4-dodecyloxy-2-hydroxy-
phenylimino)-methyl]-3-hydroxyphenyl ester之合成……………………… 41
2-4-1-7 6-Alkoxynaphthalene-2-carboxylicacid4-(6-dodecyloxy-benzooxazol-2-yl)-
3-hydroxyphenyl ester之合成……………………………………………………49
2-4-1-8 Bis[6-alkoxynaphthalene-2-carboxylic acid 4-(6- dodecyloxybenzooxazol-
2-yl)-3-hydroxyphenyl ester] copper(Ⅱ) 之合成………………………… 58
2-4-1-9 Bis[6-Alkoxynaphthalene-2-carboxylic acid 4-(6- dodecyloxyenzooxazol-
2-yl)-3-hydroxyphenyl ester] palladium (Ⅱ) 之合成…………………… 61
2-4-2 6,6’-Bis[2-(3,4,5-trialkoxyphenyl)-benzooxazole]系列之合成…………64
2-4-2-1 Methoxy-3,4,5-trialkoxybenzoate之合成………………………………………64
2-4-2-2 Methyl-3,5-dialkoxybenzoate之合成.………………………………………… 66
2-4-2-3 3,4-Dialkoxybenzoaldyhide之合成.…………………………………………… 67
2-4-2-4 4-Alkoxybenzoaldyhide之合成.………………………………………………… 68
2-4-2-5 (3,4,5-Trialkoxyphenyl)-methanol之合成…………………………………… 68
2-4-2-6 (3,5-disalkoxyphenyl)-methanol之合成……………………………………… 71
2-4-2-7 3,4,5-Trialkoxybenzoaldehyde之合成………………………………………… 71
2-4-2-8 3,5-Dialkoxybenzoaldehyde之合成………………………………………………74
2-4-2-9 4,4'-Bis[(3,4,5-trialkoxybenzylidene)amino]- biphenyl-3,3'-diol之合
成…………………………………………………………………………………… 74
2-4-2-10 4,4'-Bis[(3,4-dialkoxybenzylidene)amino]-biphenyl-3,3'-diol之合成…77
2-4-2-11 4,4'-Bis[(4-alkoxybenzylidene)amino]-biphenyl-3,3'-diol之合成………78
2-4-2-12 4,4'-Bis[(3,5-dialkoxybenzylidene)amino]-biphenyl-3,3'-diol之合成…79
2-4-2-13 6,6’-Bis[2-(3,4,5-trialkoxyphenyl)-benzooxazole]之合成………………80
2-4-2-14 6,6’-Bis[2-(3,4-dialkoxyphenyl)-benzooxazole]之合成………………… 83
2-4-2-15 6,6’-Bis[2-(3,5-dialkoxyphenyl)-benzooxazole]之合成………………… 84
2-4-2-16 6,6’-Bis[2-(4-alkoxyphenyl)-benzooxazole]之合成……………………… 85
第三章 結果與討論……………………………………………………87
3-1 反應機構探討…………………………………………………88
3-1-1 系列一化合物合成之反應機構探討…………………………88
3-1-1-1 酯化反應………………………………………………………88
3-1-1-2 硝化反應( nitration reaction )…………………………89
3-1-1-3 還原反應( Reduction reactions )……………………… 89
3-1-1-4 Schiff base反應…………………………………………… 90
3-1-1-5 Benzoxazole合環反應……………………………………… 91
3-1-2 系列二化合物合成之反應機構探討…………………………92
3-1-2-1 還原反應( Reduction reactions )……………………… 92
3-1-2-2 氧化反應………………………………………………………92
3-2 結果與討論……………………………………………………94
3-2-1 系列一之結果與討論…………………………………………94
3-2-1-1 化合物鑑定……………………………………………………94
3-2-1-2 系列一化合物液晶相之鑑定與探討…………………………96
3-2-1-3 系列一化合物2之單晶繞射數據……………………………102
3-2-1-4 系列一化合物1a及1b液晶相之鑑定與探討……………… 104
3-2-1-5 系列一化合物1a之單晶繞射數據………………………… 111
3-2-1-6 系列一化合物1a及1b其他光譜性質探討………………… 118
3-2-1-7 系列一化合物發光性質探討……………………………… 119
3-2-2 系列二之結果與討論……………………………………… 124
3-2-2-1 化合物之鑑定……………………………………………… 124
3-2-2-2 系列二化合物液晶相之鑑定與探討……………………… 125
3-2-2-3 系列二化合物發光性質探討……………………………… 129
3-3 結論………………………………………………………… 132
3-3-1 系列一之結論……………………………………………… 132
3-3-2 系列二之結論……………………………………………… 133
參考文獻…………………………………………………………………135
附圖………………………………………………………………………138

圖目錄
圖1 液晶分子設計之基本架構……………………………………………………………3
圖2 常見芳香族官能基之結構……………………………………………………………3
圖3 液相性液晶與熱相性液晶……………………………………………………………6
圖4 ( a )向列型液晶 ( nematic )、( b ) 層列性液晶 ( smectic )、
( c ) 膽固醇性液晶 ( cholesteric ) 排列方式示意圖………………………7
圖5 盤狀型液晶分子堆疊方式……………………………………………………………8
圖6 高分子型液晶分子構型………………………………………………………………9
圖7 香蕉形液晶分子衍生物………………………………………………………………10
圖8 (a) TN(STN) Mode、(b)VA Mode及(c) IPS Mode 顯示器結構示意圖………… 11
圖9 (a) TN(STN) Mode、(b) VA Mode及(c) IPS Mode常用液晶分子……………… 12
圖10 二色性液晶顯示器示意圖……………………………………………………………12
圖11 分子二色性比UV-Vis吸收圖譜示意圖………………………………………………13
圖12 可應用於OFET的桿狀型液晶分子……………………………………………………14
圖13 向列型盤狀液晶(ND)材料……………………………………………………………15
圖14 可應用於OFET之盤狀液晶材料………………………………………………………16
圖15 OLED裝置與所使用之液晶材料………………………………………………………17
圖16 太陽能電池裝置與所使用之液晶材料………………………………………………18
圖17 90級學姊胡惠美合成之液晶結構……………………………………………………19
圖18 系列二之液晶結構……………………………………………………………………20
圖19 布拉格繞射之原理……………………………………………………………………26
圖20 酯化反應機構…………………………………………………………………………88
圖21 硝化反應( nitration reaction )機構……………………………………………89
圖22 還原反應 ( Reduction reactions )機構…………………………………………90
圖23 Schiff base反應機構……………………………………………………………… 91
圖24 Benzoxazole合環反應機構………………………………………………………… 91
圖25 還原反應機構…………………………………………………………………………92
圖26 氧化反應機構…………………………………………………………………………93
圖27 化合物2之分子結構………………………………………………………………… 94
圖28 化合物1a及1b之分子結構……………………………………………………………94
圖29 化合物2相變化分析圖(cooling)……………………………………………………97
圖30 化合物2(10-12)於160 ℃下之N相偏光紋理圖…………………………………… 99
圖31 化合物2(10-12)於120 ℃下之SmC相偏光紋理圖………………………………… 99
圖32 化合物2(12-12)於95 ℃之SmC相powder X-ray繞射圖………………………… 100
圖33 化合物2(12-12)於155 ℃之N相powder X-ray繞射圖……………………………100
圖34 化合物2(12-12)以MM2模擬之分子長度……………………………………………101
圖35 分子層列傾斜角示意圖…………………………………………………………… 101
圖36 化合物2之單晶繞射分析結果………………………………………………………102
圖37 化合物2晶格之中的分子排列狀況(010)………………………………………… 102
圖38 化合物2分子排列示意圖……………………………………………………………103
圖39 化合物1a相變化分析圖(cooling)…………………………………………………105
圖40 化合物1b相變化分析圖(cooling)…………………………………………………109
圖41 化合物1a(12-12)於215 ℃下之N相偏光紋理圖………………………………… 110
圖42 化合物1a(12-12)於209 ℃下之N → SmC相轉變之偏光紋理圖…………………110
圖43 化合物1a(12-12)於205 ℃下之SmC相偏光紋理圖……………………………… 110
圖44 化合物1b(1-12)於250 ℃下之N相偏光紋理圖……………………………………110
圖45 化合物1a(6-12)的x-ray單晶繞射結構(a)(b)……………………………………111
圖46 1a分子由長軸方向觀察之單晶結構……………………………………………… 112
圖47 91級學姊李馥戎結構相似的Pd錯合物單晶結構………………………………… 113
圖48 化合物1a(6-12)分子構形………………………………………………………… 114
圖49 化合物1a(6-12)的x-ray單晶繞射結構(a)晶格(b)雙分子………………………115
圖50 1a分子間銅、氮原子間距示意圖………………………………………………… 116
圖51 化合物1a(12-12)之IR光譜圖………………………………………………………118
圖52 化合物1b(12-12)之IR光譜圖………………………………………………………118
圖53 化合物2之(a)紫外-可見光吸收光譜,(b)螢光放射光譜……………………… 119
圖54 benzoxazole結構共振示意圖(37)…………………………………………………121
圖55 (a)化合物1a、(b)化合物1b之UV-Vis 吸收光譜…………………………………121
圖56 (a)化合物1a、(b)化合物1b之螢光放射光譜…………………………………… 122
圖57 化合物3之分子結構…………………………………………………………………124
圖58 Liquid Crystals, 2005, 32, 85之結構…………………………………………126
圖59 MM2模擬之rigid core 構形……………………………………………………… 126
圖60 化合物3(n = 12)於60 ℃之結晶相偏光紋理圖………………………………… 127
圖61 化合物3(n = 6)於70 ℃之結晶相偏光紋理圖……………………………………127
圖62 化合物4(n = 12)於50 ℃之結晶相偏光紋理圖………………………………… 127
圖63 化合物6(n = 16)於160 ℃之結晶相偏光紋理圖…………………………………127
圖64 化合物3(n = 6)之MM2模擬分子結構………………………………………………128
圖65 化合物3 ~ 6之(a) UV-Vis、(b) 螢光 圖譜…………………………………… 129

表目錄
表1 常見連接官能基之結構……………………………………………………………… 4
表2 實驗所用之化學藥品…………………………………………………………………22
表3 化合物2元素分析及質譜數據……………………………………………………… 95
表4 化合物1a、1b元素分析數據…………………………………………………………95
表5 化合物2相變化數值分析…………………………………………………………… 96
表6 化合物2(12-12)的d-spacing值……………………………………………………101
表7 化合物1a相變化數值分析………………………………………………………… 104
表8 化合物2與1a進入液晶相溫度及熔點比較…………………………………………107
表9 化合物2與1a進入液晶相熱焓值比較………………………………………………107
表10 化合物1b相變化數值分析………………………………………………………… 108
表11 化合物1a(6-12)鍵長(Å)與鍵角(°)……………………………………………… 111
表12 91級學姊李馥戎結構相似的Pd錯合物鍵長(Å)與鍵角(°)……………………… 113
表13 化合物2的發光效率( quantum yield )………………………………………… 120
表14 比較不同benzoxazole結構衍生物發光效率………………………………………120
表15 化合物1a及1bUV-Vis光譜數據…………………………………………………… 122
表16 化合物3 ~ 6之元素分析及質譜數據………………………………………………124
表17 化合物3之DSC相變化數據整理表………………………………………………… 125
表18 化合物3 ~ 6 UV吸收及發光效率( quantum yield )………………………… 129
表19 比較不同benzoxazole結構衍生物發光效率………………………………………130
附圖目錄
附圖1 6-heptlyoxynathphalene-2-carboxylic acid之1H-NMR圖譜…………………… 1
附圖2 6-heptlyoxynathphalene-2-carboxylic acid之13C-NMR圖譜……………………2
附圖3 6-Hexyloxynaphthalene-2-carboxylic acid 4-formyl-3-hydroxy- phenyl
ester之1H-NMR圖譜……………………………………………………………………3
附圖4 6-Hexyloxynaphthalene-2-carboxylic acid 4-formyl- 3-hydroxy- phenyl
ester之13C-NMR圖譜………………………………………………………………… 4
附圖5 3-Dodecyloxyphenol之1H-NMR圖譜………………………………………………… 5
附圖6 3-Dodecyloxyphenol之13C-NMR圖譜…………………………………………………6
附圖7 5-Dodecyloxy-2-nitrophenol之1H-NMR圖譜……………………………………… 7
附圖8 5-Dodecyloxy-2-nitrophenol之13C-NMR圖譜………………………………………8
附圖9 2-Amino-5-dodecyloxyphenol之1H-NMR圖譜……………………………………… 9
附圖10 2-Amino-5-dodecyloxyphenol之13C-NMR 圖譜……………………………………10
附圖11 6-Hexyloxynaphthalene-2-carboxylic acid 4-[(4-dodecyloxy-2- hydroxy-
phenylimino)-methyl]-3-hydroxyphenyl ester之1H- NMR圖譜……………… 11
附圖12 6-Hexyloxynaphthalene-2-carboxylic acid 4-[(4-dodecyloxy-2-hydroxy-
phenylimino)-methyl]-3-hydroxyphenyl ester之13C- NMR圖譜………………12
附圖13 6-Dodecyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxy-benzooxazol-
2-yl)-3-hydroxyphenyl ester之1H-NMR圖譜…………………………………… 13
附圖14 6-Dodecyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzooxazol-
2-yl)-3-hydroxyphenyl ester之13C-NMR圖譜……………………………………14
附圖15 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之1H-NMR圖譜…………………………………………………………15
附圖16 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之13C-NMR 圖譜………………………………………………………16
附圖17 Methyl-3,4,5-trihexyloxybenzoate之1H-NMR圖譜………………………………17
附圖18 Methyl-3,4,5-trihexyloxybenzoate之13C-NMR圖譜…………………………… 18
附圖19 (3,4,5-Trishexadecyloxyphenyl)-methanol之1H-NMR圖譜…………………… 19
附圖20 3,4,5-trihexyloxybenzaldyhide之1H-NMR 圖譜…………………………………20
附圖21 3,4,5-trihexyloxybenzaldyhide之13C-NMR圖譜…………………………………21
附圖22 6,6’-Bis[2-(3,4,5-trihexyloxyphenyl)-benzooxazole] 之1H-NMR圖譜……22
附圖23 6,6’-Bis-[2-(3,4,5-trihexyloxyphenyl)-benzooxazole] 之13C-NMR圖譜…23
附圖24 6,6’-Bis[2-(3,4-tridodecyloxyphenyl)-benzooxazole] 之1H-NMR圖譜……24
附圖25 6,6’-Bis[2-(3,4-tridodecyloxyphenyl)-benzooxazole] 之13C-NMR圖譜… 25
附圖26 6-Dodecyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzooxazol-
2-yl)-3-hydroxyphenyl ester之MASS質譜圖…………………………………… 26
附圖27 6-Dodecyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzooxazol-
2-yl)-3-hydroxyphenyl ester之MASS質譜圖…………………………………… 27
附圖28 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之MASS質譜圖…………………………………………………………28
附圖29 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之MASS質譜圖…………………………………………………………29
附圖30 6-Dodecyloxynaphthalene-2-carboxylicacid4-(6-dodecyloxybenzooxazol-2-
yl)-3-hydroxyphenyl ester之DSC圖譜……………………………………………30
附圖31 Bis[6-dodecyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxy-
benzooxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ) 之DSC圖譜……… 31
附圖32 6-butoxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-oxazol-2-
yl)-3-hydroxyphenyl ester之DSC圖譜……………………………………………32
附圖33 Bis[6-butoxynaphthalene-2-carboxylic acid 4-(6-dodecyloxy-
benzooxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ) 之 DSC圖譜………33
附圖34 Bis[6-butoxynaphthalene-2-carboxylic acid 4-(6-dodecyloxy-
benzooxazol-2-yl)-3-hydroxyphenyl ester] palladium(Ⅱ) 之DSC圖譜……34
附圖35 Bis[naphthalene-2-carboxylic acid 4-(6-octyloxybenzooxazol-2-yl)-3-
hydroxyphenyl ester ] copper(Ⅱ) 之DSC圖譜…………………………………35
附圖36 6,6’-Bis[2-(3,4,5-trioctyloxyphenyl)-benzooxazole] 之DSC圖譜……… 36
附圖37 6,6’-Bis[2-(3,4-didodecyloxyphenyl)-benzooxazole] 之DSC圖譜…………37
附圖38 6,6’-Bis[2-(4-hexadecyloxyphenyl)-benzooxazole] 之DSC圖譜……………38
附圖39 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之單晶繞射結果………………………………………………………39
附圖40 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之單晶繞射數據(1)………………………………………………… 40
附圖41 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之單晶繞射數據(2)………………………………………………… 41
附圖42 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之單晶繞射數據(3)………………………………………………… 42
附圖43 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之單晶繞射數據(4)………………………………………………… 43
附圖44 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之單晶繞射數據(5)………………………………………………… 44
附圖45 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之單晶繞射數據(6)………………………………………………… 45
附圖46 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之單晶繞射數據(7)………………………………………………… 46
附圖47 Naphthalene-2-carboxylic acid 4-(6-butoxybenzooxazol-2-yl)-3-hydroxy-
phenyl ester之單晶繞射數據(8)………………………………………………… 47
附圖48 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射結果…………48
附圖49 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(1)…… 49
附圖50 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(2)…… 50
附圖51 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(3)…… 51
附圖52 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(4)…… 52
附圖53 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(5)…… 53
附圖54 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(6)…… 54
附圖55 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(7)…… 55
附圖56 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(8)…… 56
附圖57 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(9)…… 57
附圖58 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(10)……58
附圖59 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(11)……59
附圖60 Bis[6-hexyloxynaphthalene-2-carboxylic acid 4-(6-dodecyloxybenzo-
oxazol-2-yl)-3-hydroxyphenyl ester] copper(Ⅱ)之單晶繞射數據(12)……60
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