臺灣博碩士論文加值系統

本論文討論的主題包括兩個部份，第一部份以生醫相容的高分子材料為目標，先合成含磷脂(PC)的化合物，再接上具有光反應性的疊氮基(N3)，形成含磷脂的疊氮苯甲酸酯(N3P4)，所有合成化合物均經FT-IR、NMR、EA分析其性質，確認含有親水性的磷脂構造，將此化合物以UV 光照射接枝於PE、PP、PU 膜表面，改質後高分子膜之水面下接觸角均呈現明顯下降趨勢，顯示改質後PE、PP、PU 膜表面的確因磷脂構造而呈現親水性，ESCA 分析則顯示C、O化學位移均偏向極性基且有P、N存在，因此可以進一步確認表面含有磷脂構造，改質後PE、PP、PU 膜之血小板黏附試驗，SEM 顯示具有親水性的磷脂構造表面血小板吸附量較改質前明顯減少，而具有負電性的酸基表面血小板吸附量則並未減少，且血小板有變形活化現象，因此單純負電性並不能改善血液相容性，而擁有仿細胞膜的磷脂構造表面則可以，以溶液鑄造PU 膜比較表面形態的影響，SEM顯示靠空氣面較光滑均勻，血小板吸附量較多，而靠容器面則較粗糙，但血小板吸附量則較少，因此具親水性的兩性磷脂構造表面與表面形態的粗糙度均為改善血液相容性的要件。
第二部份以光學活性化合物的特性及其在液晶的應用為目標，先合成一系列不同碳鏈長度(n=3,6,11)之偶氮苯化合物(MnH,MnE,MnC)，POM及DSC顯示三組偶氮苯化合物中各有液晶相存在，且出現在降溫過程居多，但碳鏈長度在液晶相範圍並無簡單規律性，所合成之偶氮苯分子以UV光照射並以UV-vis分析，結果顯示具有極快速的光異構化反應(< 2 min)，也有明顯的熱回復現象，為典型的E-Z異構化反應，將此特性應用於PDLC 元件，均可以降低PDLC 元件之澄清點溫度，因此添加偶氮苯分子之PDLC元件具有影像記錄之特性。
其次合成一系列含有碳碳双鍵(C=C)光可異構化的(+)-樟腦衍生物(HnB,MnB)，探討其照射UV光時的E-Z異構化行為，及此異構化對選擇性反射光波長的影響，同時由分子結構觀點推測其光學活性差異。使用UV燈照射再以UV-vis檢測，結果顯示存在光誘發E-Z 異構化現象，但與前章的偶氮苯化合物不同，並無常溫暗回復現象，以模式化合物HBB 照射UV光，經FT-IR檢測無明顯結構破壞，NMR顯示Z-form 量大約5 %，而以旋光儀分析，比旋光度隨照光時間而漸減，30分鐘達到穩定值，變化量亦約5 %，因此推測具有光E-Z異構化行為。以線性UV 偏光照射含C=C 衍生物，再經偏光UV-vis分析，實驗顯示因E-Z 異構化使垂直偏光方向變化較大，比較一系列樟腦衍生物的比旋光度，緊鄰酮基有C=C 者比旋光度明顯較大，酮基消失或有立體障礙的exo 則較低，兩者差異極大，因此推測緊鄰酮基的C=C基之間的共振作用會增強光學活性。將含樟腦酮的光學活物添加至向列型液晶製作PSCT 元件，可調整反射光波長至可見光範圍，經UV照射後，因E-Z 異構化的擾動作用，反射光波長呈現紅位移。

There are three sections in this thesis. Firstly, an aryl azide (N3P4) containing a phosphorylcholine(PC) endgroup was synthesized and characterized by the FTIR, NMR spectra and elemental analysis. The PE, PP, PU films of which surface was grafted with N3P4 and 4-azidobenzoic acid (N31) by UV irradiation. The surface of modified films were characterized by FTIR-ATR, ESCA and contact angle measurement. ESCA shows that element P and N exist on the surface of N3P4-modified polymer films. The N3P4-modified polymer films have the lowest contact angles. The blood compatibility of the modified polymer films was evaluated with attention to platelet adhesion onto the surface. SEM observation revealed that numerous platelets adhered onto the surface of the original polymer films and polar N31-grafted films. On the other hand, few platelets adhered onto the surface of the polymer films grafted with amphiphilic N3P4. The result indicates the phosphorylcholine endgroup and morphology of the modified surface can improve hemocompatibility.
Secondly , azobenzene derivatives( MnH, MnE, MnC ) with various alkyl chain lengths were synthesized and identified by FTIR, EA and NMR .The physical properties were analyzed by DSC, TGA and POM. Liquid crystal phase exists in above azobenzene derivatives. UV-vis spectra show that all the azobenzene molecules can be photoisomerized through UV light irradiation and dark recovery. This means that azobenzene molecules exist reversible E-Z isomerization. The E-Z isomerization which irradiated by UV light can decrease the clear point of PDLC samples. This unique characteristic can be used to record image patterns.
Finally, the E-Z photoisomerizable chiral compounds were synthesized from camphor. The chiral compounds(HnB, MnB) with various alkyl spacer lengths (n= 0 ,3, 6, 9, 11)，were synthesized and identified with FTIR， NMR，and EA. Specific rotation of the chiral compounds were estimated by a Jasco DIP-360 automatic digital polarimeter with readings to ±0.003. The E-Z photo induced isomerization through C=C bonds was investigated to use UV-vis spectrophotometer. Variation of the intensity of UV-vis absorption due to the E-Z isomerization of chiral compounds was studied through various UV irradiation times. The E-Z isomerization was confirmed and it was found that the Z form of the chiral compounds is thermally stable. The results suggest that chiral compounds synthesized in this investigation can be used as a chiral dopant for the preparation of photo-imageable polymer stabilized cholesteric texture (PSCT) liquid crystal films. Compare to a series of camphor derivatives, the compounds contaning " C=C-C=O " resonance structure have higher specific rotation. Addition of chiral compounds to nematuc liquic crystal can induce the cholesteric phase. The reflective band of PSCT cell was induced a red shift by E-Z isomerization on UV irradiation.

中文摘要 I
英文摘要 III
目錄 V
流程圖目錄 IX
表目錄 X
圖目錄 XII
符號表 XX

第一章 緒論 1
1-1 生醫材料簡介 1
1-2 生醫材料與血液相容性 5
1-3 光學活性 10
1-4 光學活性之量測 11
1-5 液晶材料簡介 13
1-6 液晶的分類 14
1.7 液晶特性與量測 19
1-8 液晶的應用 22
1-9 研究動機與目的 25
1-10 參考文獻 26

第二章 磷脂衍生物高分子表面改質之血液相容性性探討 29
2-1 生醫相容原理與文獻回顧 29
2-1-1 前言 29
2-1-2 血液組成與磷脂質 31
2-1-3 血小板功能 32
2-1-4 凝血機制 37
2-1-5 生醫材料之處理及改質 39
2-1-6 磷脂質與血液相容性關係 40
2-1-7 高分子表面改質 50
2-2 實驗 53
2-2-1 藥品 53
2-2-2 儀器 54
2-2-3 合成 55
2-2-4 PE、PP、PU膜表面接枝 64
2-2-5 表面化學官能基分析 64
2-2-6 接觸角測試 64
3-2-7 表面化學分析(ESCA) 65
2-2-8 血小板吸附測試 65
2-3 結果與討論 67
2-3-1 光譜分析 67
2-3-2 表面官能基分析 80
2-3-3 接觸角測試 84
2-3-4 ESCA表面元素分析 85
2-3-5 血小板吸附測試 87
2-4 結論 101
2-5 參考文獻 102

第三章 偶氮苯衍生物之光異構化特性與應用 107
3-1 原理與文獻回顧 107
3-1-1 前言 107
3-1-2 液晶的光學異方性 107
3-1-3 液晶的光電作用 110
3-1-4 液晶高分子 112
3-1-5 光致變色與光致變機制 117
3-1-6 光及熱異構化原理 119
3-1-7 偶氮苯衍生物之異構化 122
3-1-8 含偶氮苯衍生物液晶高分子之應用 123
3-2 實驗 130
3-2-1 藥品 130
3-2-2 儀器 131
3-2-3 合成 134
3-2-4 PDLC試件的製作 138
3-2-5 偶氮苯分子之異構化特性量測 141
3-2-6 PDLC 元件之溫度–穿透度量測 141
3-2-7 偶氮苯高分子光開關之量測 142
3-3 結果與討論 143
3-3-1 合成與光譜分析 143
3-3-2 甲氧基偶氮苯衍生物之熱性質分析 154
3-3-3 偶氮苯照光異構化反應 157
3-3-4 光開關 162
3-4 結論 171
3-5 參考文獻 172

第四章 樟腦酮衍生物之光學活性與液晶應用 175
4-1 原理與文獻回顧 175
4-1-1 前言 175
4-1-2 光學活性物旋光特性 176
4-1-3 光學活性基團 178
4-1-4 含碳碳雙鍵化合物之異構化 179
4-1-5 膽固醇液晶之選擇性光反射 181
4-1-6 小分子膽固醇型液晶可逆性顏色儲存 183
4-1-7 膽固醇型液晶高分子於顏色儲存 185
4-1-8 光異構化之應用 186
4-2 實驗 192
4-2-1 藥品 192
4-2-2 儀器 193
4-2-3 合成 194
4-2-4 光學活性化合物之旋光度測試 204
4-2-5 光學活性化合物之光致變性測試 204
4-2-6 Reverse mode PSCT液晶元件的製作 205
4-2-7 選擇性光反射波長的測量 208
4-3 結果討論 209
4-3-1 合成與光譜分析 209
4-3-2 碳碳双鍵的照UV光異構化特性 233
4-3-3 碳碳双鍵照線性UV偏光之光異構化特性 241
4-3-4 含樟腦環化合物的光學活性 246
4-3-5 含樟腦基團分子在選擇性光反射系統之應用 255
4-4 結論 263
4-5 參考文獻 264

第五章 總結 267

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