臺灣博碩士論文加值系統

利用氫核磁共振光譜、13碳核磁共振光譜及元素分析來鑑定所有合成化合物的分子化學結構式。並以傅利葉紅外線光譜儀(FTIR)、微差掃描熱卡儀(DSC)、偏光顯微鏡(POM)、熱重分析儀(TGA)及廣角X光繞射儀之測量，研究所合成之新穎小分子液晶(HAMS-n 及 AMS-n) 和碳酸酯高分子(HAMS-n-PC)的液晶形態、性質及物性。
本研究首先以α-甲基二苯乙烯為液晶基，合成一系列不同長度之烷基鏈，並且烷基鏈末端是OH基的化合物，4,4’-雙-(羥基烷基氧)-α-甲基二苯乙烯，代表符號為HAMS-n (其中n是烷基鏈碳數, n= 2, 3, 4, 5, 6, 7, 8, 11)。有OH氫鍵結的新穎HAMS-n 均可呈現液晶相，烷基鏈長度影響著HAMS-n的液晶形態及性質。烷基鏈碳數是偶數的HAMS-n呈現雙向型(enantiotropic)液晶形態，而奇數之HAMS-n (除HAMS-11外)，則在冷卻過程呈現單向型(monotropic)液晶形態；HAMS-8 和HAMS-11 呈現單一晶相的CrG or CrH 液晶相，但對烷基鏈碳數小於 8 的HAMS-n，則呈現三晶相液晶相，液晶相包括CrG or CrH、SmA 及向列型液晶相。HAMS-7有多相共存。Tm及Ti隨烷基鏈碳數增加而下降，且Tm有明顯奇偶效應。
在3300-3600cm-1 吸收區的紅外線光譜分析顯示，OH伸縮振動吸收峰之原峰半寬(band half-width) 和經分解原峰後之各種氫鍵結OH吸收峰的面積比，在結晶相-CrG(or CrH) 、 CrG(or CrH)-SmA及SmA-N的轉移溫度處有明顯的不連續性；其中於SmA phase中，有無氫鍵結OH吸收峰產生，這表示末端OH基氫鍵可能是決定液晶形態的重要要素。另一方面，在400-1700cm-1指紋吸收區的光譜分析指出，以CH2彎曲及rocking progression振動為溫度的函數所得的光譜，可提供在相轉移溫度處其烷基鏈構型的起始變化之情形；而在苯環上C=C伸縮和ring skeletal振動隨溫度變化所得的光譜，也同樣可提供在苯核起始運動上的訊息。
為了探討 OH 氫鍵的效應，也同時合成末端是甲基的一系列相對應化合物，4,4’-雙-(烷基氧)-α-甲基二苯乙烯，代表符號為AMS-n(其中n是烷基鏈碳數, n= 2, 3, 4, 5, 6, 7, 9, 10, 11)。HAMS-n與AMS-n比較的結果顯示，氫鍵對液晶性質的效應主要有可促使產生雙向型液晶相、可提昇等方性液体溫度、可加寬液晶相範圍以及可促進產生排列規則度更高的層列型液晶相。
本研究接下來，利用先前所合成之HAMS-n與二苯碳酸酯進行熱熔融縮合，產生具有不同長度之亞甲基間距基的新型聚碳酸酯，Poly(-4-oxy-alkyloxy-α-methylstilbene-oxy-alkyloxy-carbonyl)，代表符號為HAMS-n-PC (其中 n 是亞甲基碳數, n= 2, 3, 4, 6, 8, 11)。熱熔融聚縮合反應所採用的反應步驟與條件能獲得介於 71~83 % 之間的良好產率和本質黏度在0.73~1.73 dL/g 之範圍的高分子量聚碳酸酯。此新型聚碳酸酯可溶於一般有機溶劑如氯仿來製得柔軟膜。
除HAMS-11-PC 外，其他所有HAMS-n-PC均呈現雙向型單一晶相的向列型液晶相。由熱重分析結果，HAMS-n-PC有高至400℃的熱裂解溫度，這顯示雖於高分子鏈引入柔軟性亞甲基，但其熱安定性與主鏈全為苯環者相當。HAMS-n-PC的 Tg、 Tm (Tm= Tk-N) 及 Ti (Ti= TN-i) 隨間距基長度增加而下降，但其熱裂解溫度卻隨間距基長度增加而增加。間距基長度也顯著影響HAMS-n-PC的液晶相範圍，研究發現間距基與液晶基的長度比值於決定液晶相的生成上扮演著重要角色。HAMS-n-PC由於分子量大和多了碳酸酯基，使得其比低分子量液晶(AMS-n)有較佳的液晶相形成能力、較穩定的液晶相以及較高的Tm和Ti值。致於HAMS-n-PC的非-直接型結構，則可促使產生雙向型液晶相、可降低Tm與Ti以及可拉寬液晶相範圍。

The chemical structures of all the synthesized compounds were characterized by 1H-NMR, 13C-NMR and elemental analysis. FTIR, DSC, POM, TGA and Wide Angle X-ray were used to study the mesomorphism and liquid crystal properties of the synthesized compounds.
This research used α-methylstilbene as mesogen. A homologues series of the compounds containing various lengths of alkyl chain terminated with hydroxyl group as spacer, 4,4’-bis(hydroxyalkyloxy)-α-methylstilbenes, denoted HAMS-n, has been synthesized. Here n is the carbon atom number of the peripheral n-alkyl chain; in this work, n= 2 to 8 and 11. All the novel HAMS-n with the OH hydrogen bonding is mesomorphic compounds. The lengths of the peripheral n-alkyl chain influenced on the mesomorphism and liquid crystalline properties. The homologues with n=8 and 11 were enantiotropic monomorphic, CrG or CrH phase. The odd homologues showed monotropic trimorphism on cooling, while the even homologues exhibited enantiotropic trimorphism including the CrG or CrH, SmA and nematic phases. The homologues with n=7 presented the co-existence of multiple mesophases. Tm and Ti were decreased with increasing of the length of n-alkyl chain and an obvious even-odd effect was observed at Tm.
The spectroscopic studied of HAMS-4 and HAMS-8 in the 3300-3600cm-1 region showed that the band half-width of overall band and the ratio of integrated intensity of the modes of hydrogen bonding of OH stretch occurred significant discontinuous at the crystalline-CrG(or CrH), CrG(or CrH)-SmA and SmA-N transitions. The free OH groups formed upon entering the SmA phase. These results indicate that the hydrogen bonding of terminal OH groups may be the important factor dominating to the morphology of liquid crystals. The spectra about the bending and rocking progression of CH2 moieties as a function of temperature suggest the onset change of the conformation of alkyl terminal chain at the temperature associated with phase transitions. The spectra on the benzene ring C=C stretch and the ring skeletal vibration as functions of temperature provide the information on the onset of motion of the phenyl mesogenic core.
In order to study the influences of OH hydrogen bonding on mesomorphic properties, a homologues series of corresponding compounds with methyl group at the terminal of terminal chain, 4,4’-bis(alkyloxy)-α-methylstilbenes, denoted AMS-n, were prepared. Here n is the carbon atom numbers of the peripheral n-alkyl chain; in this work, n= 2 to 7 and 9 to 11. The results of comparison of HAMS-n with AMS-n indicated that the hydrogen bonding effect can promote to produce enantiotropic mesophase, can increase the isotropic temperature, can broaden the temperature range of mesophase, and can promote to produce the smectic phase with higher orientational ordered such as CrG or CrH phase.
A series of novel polycarbonates with various lengths of methylene units as spacers, Poly(-4-oxy-alkyloxy-α-methylstilbene-oxy-alkyloxy-carbonyl), denoted HAMS-n-PC, were prepared from the HAMS-n and diphenyl carbonate by melt polycondensation. Here n is the numbers of methylene units in polymer chain; in this work, n= 2 to 4, 6, 8 and 11. The reaction steps and conditions used in the melt polycondensation could give good yields (71-83%) and high molecular weight polycarbonates with intrinsic viscosity in the range of 0.73-1.73 dl/g. These new polycarbonates soluble in organic solvents such as chloroform to obtain the flexible films.
Except for HAMS-11-PC, all the others HAMS-n-PC exhibited enantiotropic monomorphic nematic phase. The results of TGA showed the HAMS-n-PC had good thermal stability up to 400℃, which similar to the polymer with fully aromatic in the main chains. This indicated that the introducing of flexible methylene units into the polymer chain do not depress the decomposition temperature. Tg, Tm(Tm= Tk-N) and Ti(Ti= TN-i) were decreased with increasing of the spacer length, however, the decomposition temperatures were increased with increasing of the spacer length. The spacer lengths were also influenced on the temperature range of mesophase of HAMS-n-PC and found that the relative length of spacer to mesogen played an important role in the mesophase formation. The increasing of the molecular weight and having a carbonate linkage in the chain lead the HAMS-n-PC have better mesogenity, more stable mesophase, and higher Tm and Ti than the low molecular weight liquid crystals (AMS-n). The non-directed type structure in the polymer chain of HAMS-n-PC, can promote to produce enantiotropic mesophase, can lower the Tm and Ti , and broaden the temperature range of mesophase.

封面
中文摘要
英文摘要
誌謝
目錄
圖目錄
表目錄
第一章、諸論
第二章、文獻回顧
2-1　液晶分子的基本結構與液晶性質
2-1-1　柔軟鏈段的效應
2-1-2　核的效應
2-1-3　連接基因的效應
2-1-4　末端基因的效應
2-1-5　側邊取代基的效應
2-2　液晶晶相的種類
2-3　主鏈型聚碳酸酯液晶高分子的合成
2-4　主鏈型液晶高分子的分子結構與液晶性質的關係
2-4-1　液晶基的效應
2-4.2　間距基的效應
2-4-2-1　聚甲烯基間距基
2-4-2-2　聚乙烯氧間距基
2-4-2-3　聚矽氧烷間距基
2-4-2-4　間距基上取代基效應
2-5　直接連接型結構與非－直接連接型結構的分子結構
第三章、實驗部份
3-1　實驗藥品
3-2　合成
3-2-1.4，4''－二羥基－α－甲基二苯乙烯（HMS）
3-2-2.4，4''－雙－（ｗ－羥基烷基氧）－α－甲基二苯乙烯（HAMS－ｎ）
3-2-3.4，4''－雙（W－烷基氧）－α－甲基二苯乙烯（AMS－ｎ）
2-2-4　相容性測試方法中所用到的參考物
3-2-5　Poly(-4-oxy-alkyloxy-α-methystilbene-oxy-alkyloxy-carbonyl)(HAMS-n-PC聚碳酸酯)
3-3 儀器設備
3-4 結構鑑定
3-4-1.4，4''-雙-(羥基烷基氧)-α-甲基二苯乙烯(AMS-n)
3-4-4 相容性測試方法中所用到的參考物
3-4-5 Poly(-4-oxy-alkyloxy-α-methylstilbene-oxy-alkyloxy-carbonyl)(HAMS-n-PC聚碳酸酯)
第四章 4，4''-雙-(羥基烷基氧)-α-甲基苯乙烯與4，4''-雙-(烷基氧)-α式-甲基二苯乙烯的合成、液晶形態及氫鍵效應
4-1 前言
4-2 HAMS-n及AMS-n的合成反應
4-3 HAMS-n的液晶形態
4-3-1 浣基鍵碳數是偶數之HAMS-n(n=2，4，6)
4-3-2 烷基鍵碳數是奇數之HAMS-n(n=3，5，7)
4-3-3 HAMS-8和HAMS-11
4-4 HAMS-n的熱向性質
4-5 HAMS-7的特殊現象
4-6 AMS-n的液晶形態及性質
4-7 HAMS-n與AMS-n的液晶性質比較
4-8 結論
第五章 4，4''-雙-(羥基烷基氧)-α-甲基二苯乙烯之紅外線光譜分析與液晶形態
5-1 前言
5-2 紅外線光譜分析
5-2-1 OH伸縮振動吸收區
5-2-2 400-1700cm-1 吸收區
5-3 結論
第六章 含α-甲基二苯烯液晶基之新穎液晶聚碳酸酯的合成液晶形態與性質
6-1 前言
6-2 聚合反應
6-3 有機溶劑的溶解性
6-4 熱轉移行為
6-5 液晶紋理與晶態
6-6 晶相、晶相變化與分子構造的關係
6-7 熱安定性
6-8 結論
第七章 總結論
參考文獻
自述
著作目錄

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