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研究生：	洪逸樺 Hung, Yi-Hua
論文名稱：	具光子特性手性向列型液晶在感測及顯示元件上的應用研究 Study on The Applications of Photonic Chiral Nematic Liquid Crystals on Sensors and Displays
指導教授：	劉瑞祥 Liu, Jui-Hsiang
學位類別：	博士 Doctor
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2021
畢業學年度：	109
語文別：	英文
論文頁數：	176
中文關鍵詞：	膽固醇液晶、手性向列型液晶、溶致型、熱致型、布拉格反射、兩性、雙穩態裝置、雙頻液晶、鐵電性液晶
外文關鍵詞：	cholesteric liquid crystals, chiral nematic liquid crystals, lyotropic, thermotropic, Bragg reflection, amphitropic, bistable device, dual-frequency liquid crystals, ferroelectric liquid crystals
相關次數：	點閱：171 下載：0
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液晶材料是一種存在於固相和液相之間的中間相材料。液晶具有與常規液體相同的各向同性，同時也具有與結晶固體相同的各向異性。具有特殊排列或對稱性的中間相液晶分子可分為主要三類：向列型、膽固醇型和層列型。液晶材料的特殊性質能將會受到溫度、電場、磁場和應力等外部刺激。因此液晶材料在顯示器、光柵裝置和感測裝置的開發中具有巨大的應用潛力。
為了研究手性向列型液晶材料在傳感器和液晶顯示器上的應用，合成了一系列手性材料並將其應用於傳感器和液晶顯示器。
第二章主要探討了膽固醇衍生的手性兩親性液晶的合成及其熱和光學性質。合成自膽固醇和肉桂酸的手性單體膽固醇肉桂酸酯（CCM），其結果顯示出兩親性液晶相。合成的CCM在偏振光學顯微鏡（POM）下顯示出油膩的條紋紋理，對應於加熱至120℃以上並用有機溶劑如二氯甲烷、氯仿、四氫呋喃和甲苯處理後形成的膽固醇液晶相。熱向型和溶致膽固醇液晶都顯示出選擇性的光反射，並且反射光的波長落在可見光區域中，呈現出五顏六色的外觀。結果表明CCM可用於開發溫度和溶劑傳感器。
第三章主要通過手性向列型液晶混合物的光聚合製備印跡光子膜。聚合後，將手性摻雜劑CB15去除並回收。印跡光子膜在沒有手性摻雜劑的情況下顯示出布拉格反射。感測水溶液中的溶劑後，肉眼和紫外光光譜儀分別觀察到顯著的顏色變化和位移峰。此外，還研究了通過印跡光子膜檢測甲醇，乙醇和丙酮中氯仿的含量。結果表明，印跡光子膜可以檢測不同種類的混合溶劑。通過與羅丹明衍生的單體共聚，進一步提高了印跡光子膜的感測功能。合成的改性印跡光子膜可以檢測水溶液中的重金屬離子。這項研究結果成功展現了新型感測薄膜不只可以檢測水溶液中的有機溶劑，同時也能檢測重金屬離子。
第四章我們合成了預先設計的功能單體液晶（4NN），並將其與雙頻膽固醇液晶混合以製造雙頻雙穩態液晶裝置。4NN單體除乙烯基外還含有一個羰基。由於單體結構的設計，功能單體4NN將被聚合成聚合物鏈。雙頻膽固醇液晶使用了雙頻向列液晶HEF951和自行預先合成的手性鐵電液晶3C所獲得。雙頻向列型液晶通過驅動電壓下高低頻交流電場的控制，提供了一種操作這些雙穩態液晶裝置的新方法。手性鐵電液晶3C用於誘導形成向列型液晶的膽固醇液晶相，並降低所製造的雙頻雙穩態液晶裝置的驅動電壓和響應時間。所製造的雙頻雙穩態液晶裝置在一次開和關切換之後顯示出穩定的不透明焦錐態（Focal Conic State）和穩定的透明平面態（Planar State），且不需要能量來維持相態。結果顯示出新設計後的雙頻雙穩態液晶裝置相較於過去的研究有更好的透射率和更快的響應時間。

Liquid crystal materials are mesophases existing between solid and liquid. Liquid crystals show similar fluidity as conventional liquids and reveal anisotropy as crystalline solids. Liquid crystal molecules with special arrangement or symmetry can be divided into three main categories: nematic, cholesteric and smectic. Liquid crystals are sensitive to external stimuli such as temperature, electric field, magnetic field, and stress. Accordingly, liquid crystals have great potential in the development of display, grating devices and sensing devices.
To study the applications of chiral nematic liquid crystals on sensors and liquid crystal displays, a series of chiral materials were synthesized and their applications on sensors and displays were carried out.
In Chapter 2, synthesis of chiral amphitropic liquid crystals derived from cholesterol and study of their thermal and optical properties were carried out. Chiral monomeric cholesteryl cinnamate (CCM) derived from cholesterol and cinnamic acid has been synthesized, showing amphitropic liquid crystal phases. The synthesized CCM exhibits oily streak textures under a polarized optical microscopy (POM), corresponding to the cholesteric liquid crystal phase formed after heating over 120°C and after being treated with organic solvents such as dichloromethane, chloroform, tetrahydrofuran, and toluene. Both the thermotropic and lyotropic cholesteric liquid crystals exhibit selective light reflection, and the wavelength of the reflected light falls in the visible light region showing colorful appearances. The results suggest that CCM could be used for the development of sensors for both temperature and solvents.
In Chapter 3, preparation of imprinted photonic films by photopolymerization of chiral nematic liquid crystal mixture was carried out. After polymerization, the chiral dopant, CB15, was removed and recycled. The imprinted photonic polymer films showed Bragg reflection without the presence of the chiral dopant. Upon sensing solvents in an aqueous solution, significant color changes and peak shifts were observed by the naked eye and ultraviolet-visible spectroscopy, respectively. Furthermore, the sensing of chloroform content in methanol, ethanol, and acetone via the imprinted film was also investigated. The results suggest that the synthesized imprinted photonic films can detect different kinds of mixed solvents. The sensing properties of the photonic films were further improved by copolymerization with a rhodamine-derived monomer. The synthesized modified photonic films can detect heavy metal ions in an aqueous solution. This study successfully demonstrated that the new sensing film could detect not only organic solvents in aqueous solutions but also detect heavy metal ions.
In Chapter 4, we synthesized a pre-designed functional monomeric liquid crystal (4NN) and mixed it with the dual-frequency cholesteric liquid crystal to make bistable dual-frequency liquid crystal devices. The 4NN monomer contains a carbonyl group in addition to the vinyl group. Due to the design of the monomer structure, the functional monomer 4NN was introduced into polymer chain. The dual-frequency cholesteric liquid crystal is obtained using the dual-frequency nematic liquid crystal HEF951 and the pre-synthesized chiral ferroelectric liquid crystal 3C. Dual-frequency nematic liquid crystals provide a reversible switching of bistable liquid crystal devices with each of high and low-frequency AC electric fields under driving voltage. The chiral ferroelectric liquid crystal 3C is used to induce the formation of cholesteric liquid crystal phase and reduce the manufactured bistable dual-frequency liquid crystal device's driving voltage and response time. The manufactured bistable dual-frequency liquid crystal device exhibits a stable opaque focal conic state and a stable transparent planar state after one time on and off switching without any energy to maintain. The results show that the newly designed bistable dual-frequency liquid crystal device reveals better transmittance and faster response time than previous studies.

Abstract I
中文摘要 IV
誌謝 VI
Contents VII
List of Schemes XIII
List of Tables XIV
List of Figures XV
Chapter 1 1
General Introduction and Theoretical Background 1
1-1 Preface 1
1-2 Introduction of Liquid Crystals 2
1-3 Classification of Liquid Crystals 4
1-3-1 Thermotropic Liquid Crystals 5
1-3-1-1 Nematic Liquid Crystal Phase 6
1-3-1-2 Smectic Liquid Crystal Phase 7
1-3-1-3 Cholesteric Liquid Crystal Phase 9
1-3-1-4 Discotic Liquid Crystal Phase 14
1-3-2 Lyotropic Liquid Crystals 15
1-4 Physical Properties of Liquid Crystals 17
1-4-1 Anisotropic Properties of Liquid Crystals 17
1-4-2 Birefringence of Liquid Crystals[36] 18
1-4-3 Dielectric Properties of Liquid Crystals 20
1-4-4 Identification of Thermotropic Liquid Crystals 22
1-5 Dual-Frequency Liquid Crystals (DFLC) 25
1-6 Ferroelectric Liquid Crystals (FLC) 28
1-7 Polymer Stabilized Cholesteric Liquid Crystals 30
1-7-1 Planar Cholesteric Texture[54] 30
1-7-2 Focal-Conic Texture[54] 31
1-7-3 Homeotropic Texture[54] 31
1-7-4 Polymer Network 32
1-7-5 Polymer Stabilized Cholesteric Liquid Crystals (PSCLC) 34
1-8 Introduction of Photopolymerization Reaction 36
1-9 Introduction of Cholesterol Lyotropic Liquid Crystals 37
1-10 Bistable Liquid Crystal Display 42
1-11 Research Motivations 46
1-12 References 48
Chapter 2 57
Thermal and Optical Properties of Amphitropic Liquid Crystals Derived from Cholesterol and Cinnamic Acid 57
Abstract 57
2-1 Introduction 58
2-2 Materials and Methods 60
2-2-1 Experimental 60
2-2-2 Materials 60
2-2-3 Instruments 61
2-2-4 Synthesis of 4-(6-hydroxyhexyloxy) Cinnamic Acid (1) 62
2-2-5 Synthesis of 4-(6-acryloyloxyhexyloxy) Cinnamic Acid (2) 63
2-2-6 Synthesis of cholesteryl-4-(6-acryloyloxyhexyloxy) cinnamate (CCM) 64
2-2-7 Synthesis of Homopolymer (Poly-CCM) 68
2-3 Results and Discussion 68
2-3-1 Mesomorphic Properties of Monomer CCM 69
2-3-2 Lyotropic Liquid Crystalline Behaviour of CCM 77
2-3-3 Thermal and Optical Properties of Lyotropic Liquid Crystalline CCM 80
2-3-4 Partially Polymerised CCM 82
2-3-5 Synthesis and Thermal Properties of Poly-CCM 83
2-3-6 Liquid Crystal Behaviours of Poly-CCM 85
2-4 Conclusions 86
2-5 References 88
Chapter 3 93
Fabrication of Imprinted Photonic Films via Predesigned Multiple UV-Polymerizations and Their Ability to Detect Solvents and Metal Ions in Aqueous Solution 93
Abstract 93
3-1 Introduction 94
3-2 Experimental Section 96
3-2-1 Materials 96
3-2-2 Instruments 97
3-3 Synthesis of bifunctional 4,4'-bis (6-(acryloyloxy) hexyloxy) biphenyl (BAHB) Monemer[34] 97
3-3-1 Synthesis of 4,4'-bis (6-hydroxyhexyloxy) biphenyl 97
3-3-2 Synthesis of BAHB 98
3-3-3 Synthesis of Rhodamine Hydrazone-FSLC074 Monomer (Rh-FSLC074) 99
3-3-4 Preparation of Imprinted LC Films 102
3-3-5 Preparation of LC Films via Regular UV Polymerization 105
3-4 Results and Discussion 106
3-4-1 Observation of Mixture 106
3-4-2 Optical Characterization of Imprinted Films 107
3-4-3 Dependence of Reflection Band of Imprinted Films on Organic Solvents 108
3-4-4 Sensing Characterization of Imprinted Film on Mixed Organic Solvents 110
3-4-5 Sensing Characterization of Imprinted Film on Toxic Chemicals in Aqueous Solution 113
3-4-6 Selectivity of Ion Detection of the Rhodamine-Derived Monomer 115
3-4-7 Optical Characterization of Copper Ions via CLC Imprinted Film 116
3-5 Conclusions 119
3-6 References 120
Chapter 4 125
Fabrication of High Contrast and Fast Response Bistable Dual-Frequency CLC Cells 125
Abstract 125
4-1 Introduction 126
4-2 Experimental Section 130
4-2-1 Materials 130
4-2-2 Instruments 130
4-2-3 Synthesis of Ferroelectric Liquid Crystal 3C 131
4-2-3-1 Synthesis of (R)-butyl 2-(4-hydroxyphenoxy)propanoate (1A) 131
4-2-3-2 Synthesis of (S)-4'-((3,7-dimethyloct-6-en-1-yl)oxy)-(1,1'-biphenyl)-4- carboxylic acid (2C) 132
4-2-3-3 Synthesis of 4-(((R)-1-butoxy-1-oxopropan-2-yl)oxy)phenyl 4'-(((S)-3,7-dimethyloct-6-en-1-yl)oxy)-(1,1'-biphenyl)-4-carboxylate (3C) 133
4-2-4 Synthesis of Functional Monomer 4NN 134
4-2-4-1 Synthesis of (R)-butyl 2-(4-hydroxyphenoxy)propanoate (1A) 134
4-2-4-2 Synthesis of 4'-((6-hydroxyhexyl)oxy)-(1,1'-biphenyl)-4-carboxylic acid (2NN) 134
4-2-4-3 Synthesis of 4'-((6-(acryloyloxy)hexyl)oxy)-(1,1'-biphenyl)-4-carboxylic acid (3NN) 135
4-2-4-4 Synthesis of (R)-4-((1-butoxy-1-oxopropan-2-yl)oxy)phenyl 4'-((6-(acryloyloxy)hexyl)oxy)-(1,1'-biphenyl)-4-carboxylate (4NN) 136
4-2-5 Preparation of CLC Mixture 137
4-2-6 Fabrication of Polymer Stabilized CLC Cells 139
4-2-7 Measurement of Electro-Optical Properties 139
4-3 Results and Discussion 140
4-3-1 Components of CLC Mixtures 140
4-3-2 Characterization of the Synthesized Compounds 141
4-3-2-1 Structure Identification 141
4-3-2-2 Thermal Properties Analysis 147
4-3-2-3 Optical Properties Analysis 151
4-3-2-4 Ferroelectric Properties Analysis 153
4-3-3 Characterization of Polymer Stabilized Cells 155
4-3-3-1 Electro-Optical Properties of Bistable Sample Cells 155
4-3-3-2 Response Time of Bistable Sample Cells 160
4-3-3-3 Stability of Fast Response BDFCLC Device 162
4-3-3-4 Transparency of Fast Response BDFCLC Device in Visible Light Region 164
4-3-3-5 Thermal Properties of Fast Response BDFCLC Mixture 165
4-4 Conclusions 166
4-5 References 168
Chapter 5 172
Conclusions 172
Appendix 174
                                    

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Chapter 2
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Chapter 3
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