具有benzoxazole結構之無機液晶材料

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姓名

江佩儀(Pei-yi Chiang) 查詢紙本館藏

畢業系所

化學學系

論文名稱

具有benzoxazole結構之無機液晶材料

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摘要(中)

本論文主要分為兩個系列之合成與研究，所有的化合物經由1H-NMR、13C-NMR、Mass與元素分析以鑑定其結構與純度，液晶相性質則是利用偏光顯微鏡(POM)、熱差式掃描卡計儀(DSC)及Powder X-ray來觀察測量。
系列一為合成化合物1；3-Alkoxy-6-[(4-alkoxy-2-hydroxy- phenylimino)- methyl]-benzene-1,2-diol及化合物2；2-Hydroxy-4- alkoxyl-N-(2-hydroxy-4- alkoxybenzylidene)anilines，探討側鏈基的數目以及碳鏈長短對液晶相的影響。化合物1的分子都具有SmC及SmA的液晶相，而化合物2的分子都具有SmC的液晶相。由於這兩個分子結構只差在一OH官能基，我們試著去解釋為什麼有這樣的排列變化，做了變溫IR的測量，而其實驗結果證實其化合物1具有分子間的氫鍵，而Powder X-ray的數據亦證實為層狀液晶的排列。
系列二為合成出配位基2,3-dialkoxyl-6-(6-alkoxyl-benzooxazol- 2-yl)-phenol，所有的配位基都不具有液晶性質。接著，我們將配位基與鋅金屬進行配位，得到單金屬無機液晶，且為所預期的盤狀液晶。錯合物的澄清點皆比配位基提高約30~80 ℃。然而，當我們將配位基與金屬Cu和Pd進行錯合時，皆不具任何液晶相。由Powder X-ray的數據，我們得知錯合物的排列為Colr，其space group是為P21。

摘要(英)

In this thesis, we report the synthesis, characterization and mesomorphic properties of two novel series of new mesogenic derivatives based on 3-Alkoxy-6-[(4-alkoxy-2-hydroxy-phenylimino)- methyl]-benzene-1,2-diol 1 and metal complexes of 2,3-dialkoxyl-6-(6- alkoxyl-benzooxazol-2-yl)-phenol. These compounds were all characterized by 1H-NMR and 13C-NMR spectroscopy, and their mesomorphic properties were studied by differential scanning calorimeter (DSC), polarized optical microscopy (POM) and powder XRD diffraction.
For the first series of 3-Alkoxy-6-[(4-alkoxy-2-hydroxy-phenylimino) -methyl]-benzene-1,2-diol 1 and 2-Hydroxy-4- alkoxyl-N-(2-hydroxy-4- alkoxybenzylidene)anilines 2, all compounds exhibited smectic phases. Compounds 2 exhibited mesomorphic behavior similarly to compounds 1. In contrast, compounds 2 have higher melting points and wider mesogenic temperatures than 1.
In the second series of derivatives; the compounds of 2,3-dialkoxyl -6-(6-alkoxyl-benzooxazol-2-yl)-phenol as ligands were not mesogenic. However, the zinc(Ⅱ) complexes exhibited columnar rectangular (Colr, P21) phases, as predicted for disc molecules. The melting point of zinc complexes is ca. 30~80 ℃ higher than their metal-free ligands. However, palladium(Ⅱ) and copper(Ⅱ) complexes were not mesogenic.

關鍵字(中)

★ 液晶

關鍵字(英)

★ liquid crystal

論文目次

中文摘要…………………………………………………Ⅰ
英文摘要………………………………………………Ⅱ
謝誌………………………………………………………Ⅲ
目錄………………………………………………………Ⅳ
圖目錄…………………………………………………………Ⅸ
表目錄…………………………………………………ⅩⅡ
附圖目錄………………………………………………ⅩⅢ
第一章緒論……………………………………………1
1-1 前言……………………………………………2
1-2 液晶之來源與簡介……………………………2
1-3 液晶分子結構…………………………………3
1-4 液晶之分類………………………………….4
1-5 Schiff base型液晶…………………………11
1-6 雜環液晶……………………………………15
1-7 無機液晶……………………………………17
1-8 液晶之應用……………………………………20
1-9 研究動機………………………………………21
第二章實驗部份………………………………………23
2-1 實驗藥品………………………………………24
2-2 儀器設備……………………………………25
2-3 實驗流程……………………………………34
2-3-1 系列一之實驗流程……………………………34
2-3-2 3-Alkoxyphenols之合成……………………35
2-3-3 5-Alkoxy-2-nitrophenols之合成…………37
2-3-4 2-Amino-5-Alkoxyphenols之合成........39
2-3-5 4-Alkoxy-2,3-dihydroxybenzaldehyde之合成…….…40
2-3-6 3-Alkoxy-6-[(4-alkoxy-2-hydroxy-phenylimino)-methyl]-benzene-1,2-diol之合成…...........................................43
2-3-7 3-Alkoxy-6-[(2-hydroxy-phenylimino)-methyl]-benzene-1,2-diol之合成.............................................47
2-3-8 4-Alkoxy-2-hydroxybenzaldehyde 之合成……………48
2-3-9 2-Hydroxy-4-alkoxyl-N-(2-hydroxy-4-alkoxybenzylidene) anilines之合成…………………49
2-3-10 5-alkoxy-2-[(2-hydroxy-phenylimino)-methyl]-phenol之合成……….......................................51
2-4 實驗流程………………………………………53
2-4-1 系列二之實驗流程……………………………53
2-4-2 3,4-Dialkoxy-2-hydroxybenzaldehyde 之合成………...54
2-4-3 2-Hydroxy-4-alkoxyl-N-(2-hydroxy-3,4-dialkoxybenzylidene) anilines之合成………………56
2-4-4 2,3-dialkoxyl-6-(6-alkoxyl-benzooxazol-2-yl)-phenol之合成……………………………………58
2-4-5 Bis[2,3-alkoxyl-6-(6-alkoxyl-benzooxazol-2-yl)-phenol]zinc(II)之合成.............................................61
2-4-6 Bis[2,3-alkoxyl-6-(6-alkoxyl-benzooxazol-2-yl)-phenol]copper (II)之合成……63
2-4-7 Bis[2,3-alkoxyl-6-(6-alkoxyl-benzooxazol-2-yl)-phenol] palladium(II)之合成…………………….........................63
第三章結果與討論……………………………………65
3-1 系列一…………………………………………66
3-1-1 反應機構之探討………………………………67
3-1-2 化合物之鑑定…………………………………70
3-1-3 熱分析數據……………………………………70
3-1-4 偏光紋理圖……………………………………75
3-1-5 IR光譜數據分析………………………………77
3-1-6 powder X-ray之探討…………………………80
3-2 系列二…………………………………………84
3-2-1 反應機構之探討………………………………85
3-2-2 配位基之討論…………………………………86
3-2-2-1 熱分析數據…………………………………86
3-2-2-2 IR光譜數據分析……………………………88
3-2-3 鋅錯合物之討論………………………………88
3-2-3-1 熱分析數據……………….…………………89
3-2-3-2 IR光譜數據分析…………………………….92
3-2-4 偏光紋理圖……………………………………92
3-2-5 與其他不同金屬配位…………………………94
3-2-6 powder X-ray之探討…………………………95
3-2-7 其他性質之探討………………………………99
3-3 結論…………………………………………103
參考文獻.....................................104

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指導教授

賴重光(Chung-Kung Lai)

審核日期

2005-7-14

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