臺灣博碩士論文加值系統

本研究的主要目的是合成兩系列的新旋光性液晶材料HNP(p,n,2)。藉著改變液晶材料的分子結構上的非旋光末端烷鏈及在酯基和燕尾結構的烷基間增加一個甲基，以探討結構變化對液晶相及其物性的影響，以建立分子結構與旋光性液晶相物性的關係。
化合物HNP(p,0,2; p=8~14) 都具有Iso-N*-TGBA-SA-SCA*-Cr.的相轉移順序。由化合物的電流轉換行為、自發極化值、介電性質及光電應答的研究結果顯示SCA*相具有無閥反誘電的特性。延長化合物HNP(p,0,2)非旋光末端烷鏈的長度p對SCA*相中的電流轉換行為、自發極化值及介電性質的量測結果並沒有顯著的影響。在無閥反誘電液晶相中，化合物HNP(p,0,2)之適當長度非的旋光末端烷鏈可得到良好的V形轉換。
化合物HNP(p,1,2; p=9~14) 大多只具有Iso -SA-SCA*-Cr.的相轉移順序。而在非旋光末端烷鏈長度p=11~12的化合物中，發現溫度範圍為0.1~02℃的N*相及TGBA相。由化合物的電流轉換行為、自發極化值、介電性質及光電應答的研究結果顯示SCA*相具有無閥反誘電的特性。延長化合物HNP(p,1,2)非旋光末端烷鏈的長度p對SCA*相中的電流轉換行為、自發極化值及介電性質的量測結果並沒有顯著的影響。在無閥反誘電液晶相中，化合物HNP(p,1,2)之適當長度非的旋光末端烷鏈可得到良好的V形轉換。
在研究酯基和燕尾結構的烷基間增加一個甲基對於電流轉換、自發極化值、介電性質及光電應答並沒有顯著的不同。
綜合以上結果得知兩系列HNP(p,0,2) 及HNP(p,1,2)的化合物均有反誘電性液晶相，SCA*相。此SCA*相均可獲得良好的V-型轉換行為，證實此類液晶相為無閥反誘電性液晶相。至於酯基和燕尾結構的烷基間增加一個甲基，則對於V-型轉換行為並沒有顯著的改變。在無閥反誘電液晶相中，化合物HNP(p,0,2)及HNP(p,1,2)之適當長度非的旋光末端烷鏈都可得到良好的V形轉換。

The purpose of this research work was an attempt to elucidate the structure-property correlation in the chiral smectic liquid crystals, because the exciting results have been obtained this field of chiral system. A homologous series of chiral materials HNP(p,n,2) was designed for the synthesis and investigation of the structure-property relationship in the chiral liquid crystal system. The target compounds was modified independently by the length of the alkyl chain p and n methylene group for the study.
Compounds HNP(p,0,2; p=8~14) have the Iso-N*-TGBA-SA-SCA*-Cr. transitions. The study of dielectric property, switching behavior and electro-optical response demonstrates that these chiral materials in the antiferroelectric SCA* phase possess thresholdless antiferroelectricity. The variations of peripheral chain length, p, in the series of compounds HNP(p,0,2) have no remarkable effect on spontaneous polarization, dielectric property and switching behavior in the SCA* phase. The moderate peripheral chain length of HNP(p,0,2) favors the formation of good V-shaped switching behavior in the thresholdless SCA* phase.
Compounds HNP(p,1,2; p=9~14) mostly have the Iso-SA-SCA*-Cr. transitions. In the compounds with non-chiral peripheral chain length p=11~ 12, a N* phase and a TGBA phase with the temperature range of 0.1~0.2℃were detected. The study of dielectric property, switching behavior and electro-optical response demonstrates that these chiral materials in the antiferroelectric SCA* phase possess thresholdless antiferroelectricity. The variations of peripheral chain length, p, in the series of compounds HNP(p,1,2) have no remarkable effect on spontaneous polarization, dielectric property and switching behavior in the SCA* phase. The moderate peripheral chain length of HNP(p,1,2) favors the formation of good V-shaped switching behavior in the thresholdless SCA* phase.
Investigating the effect of additional methylene group between carboxyl group and swallow-tailed group on the switching behavior, spontaneous polarization, dielectric properties, and electro-optical responses for these compounds also indicate that there has no remarkable difference.
In conclusion, the results from above indicate that of HNP(p,0,2) and HNP(p,1,2) possess antiferroelectric phase, SCA* phase. Good V-shaped switching behavior achieved in the SCA* phase, demonstrating the existence of thresholdless antiferroelectricity. It also indicates additional methylene group (n=1) between carboxyl group and swallow-tailed group has no remarkable effect on V-shaped switching behavior. The moderate peripheral chain length of HNP(p,0,2) and HNP(p,1,2) favors the formation of good V-shaped switching behavior in the thresholdless SCA* phase.

TABLE OF CONTENTS
ACKNOWLEDGMENTS III
ABSTRACT IV
中文摘要 VI
TABLE OF CONTENTS VIII
LIST OF SCHEME XI
LIST OF TABLES XII
LIST OF FIGURES XIII
CHAPTER 1
INTRODUCTION 1
1.1 Overview 1
1.2 Chiral nematic phase or cholesteric phase 1
1.3 Smectic phase 3
1.3.1 Smectic A phase 3
1.3.2 Smectic C* phase or ferroelectric phase 5
1.3.3 Antiferroelectric phase 10
1.4 Frustrated phases 16
1.4.1 Double twist blue phase 16
1.4.2 Twist grain boundary phases 19
1.5 Motivation of study 19
CHAPTER 2
EXPERIMENTAL 26
2.1 Preparation of materials 26
2.1.1 Synthesis of 4-(4’-alkoxyphenyl)benzoic acids, PBA(p) 28
2.1.2 Synthesis of 1-ethylpropyl (s)-2-(6-methoxy-2-naphthyl) propio-nates, MNP(0,2) 29
2.1.3 Synthesis of 1-ethylpropyl (s)-2-(6-hydroxy-2-naphthyl) propio-nates, HNP(0,2) 29
2.1.4 Synthesis of 1-ethylpropyl (s)-2-(6-(4-(4’-alkoxy-phenyl)benzoyl-oxy)-2-naphthyl)propionates, HNP(p,0,2) 30
2.1.5 Synthesis of 2-ethylbutyl (s)-2-(6-methoxy-2-naphthyl) propio-nates, MNP(1,2) 31
2.1.6 Synthesis of 2-ethylbutyl (s)-2-(6-hydroxy-2-naphthyl) propio-nates, HNP(1,2) 31
2.1.7 Synthesis of 2-ethylbutyl (s)-2-(6-(4-(4’-alkoxy-phenyl)benzoyl-oxy)-2-naphthyl)propionates, HNP(p, 1,2) 31
2.2 Characterization of materials 32
2.2.1 Chemical structure identification 32
2.2.2 Mesophase identification 34
2.2.4 Spontaneous polarization measurement 40
2.2.5 Dielectric constant measurement 41
2.2.6 Optical response measurement 42
CHAPTER 3
RESULTS and DISCUSSION 44
3.1 1-Ethylpropyl (s)-2-(6-(4-(4'-alkoxyphenyl) benzoyl-oxy)-2-naphthyl) propionates, HNP(p,0,2) 44
3.1.1 Mesomorphic properties 44
3.1.2 Calorimetry studies 47
3.1.3 Switching behavior 54
3.1.4 Spontaneous polarization 57
3.1.5 Dielectric properties 57
3.1.6 Electro-optical responses 57
3.2 2-Ethylbutyl (s)-2-(6-(4-(4'-alkoxyphenyl)benzoyl-oxy)-2-naphthyl) propionates, HNP(p,1,2) 72
3.2.1 Mesomorphic properties 72
3.2.2 Calorimetry studies 75
3.2.3 Switching behavior 82
3.2.4 Spontaneous polarization 86
3.2.5 Dielectric properties 86
3.2.6 Electro-optical responses 90
CHAPTER 4
CONCLUSIONS 101
REFERENCES 103
APPENDIX 108
LIST OF SCHEME
Scheme 2.1 Synthetic procedures for the compounds 1- and 2-ethylalkyl (s)-2-(6-(4-(4’-alkoxyphenyl)benzoyloxy)-2-naphthyl)propionates, HNP(p, n,2). 27
LIST OF TABLES
Table 2.1 Chemical shifts of 1H NMR for intermediates MNP(n,2). 35
Table 2.2 Chemical shifts of 1H NMR for intermediates HNP(n,2). 35
Table 2.3 Chemical shifts of 1H NMR of compounds HNP(p,0,2). 36
Table 2.4 Chemical shifts of 1H NMR of compounds HNP(p,1,2). 37
Table 2.5 Results of elemental analysis and physical data of specific rotation for intermediates HNP(n,2). 38
Table 2.6 Results of elemental analysis and physical data of specific rotation for compounds HNP(p,0,2). 38
Table 2.7 Results of elemental analysis and physical data of specific rotation for compounds HNP(p,1,2). 39
Table 3.1 Transition temperature and enthalpies DH(in italics) of materials HNP(p,0,2) at 5℃/min scanning rate. 52
Table 3.2 Transition temperature and enthalpies DH(in italics) of materials HNP (p,1,2) at 5℃/min scanning rate. 80
LIST OF FIGURES
Figure 1.1. The melting process of a calamitic (rod-like) liquid-crystalline material. 2
Figure 1.2 Helical structure of the chiral nematic 4
Figure 1.3 The structure of smectic A phase 6
Figure 1.4 Symmetry operations in the smectic C and chiral smectic C* phase. 6
Figure 1.5 Helical macrostructure of the chiral smectic C* phase. 8
Figure 1.6 Schematic representation of a "surface stabilized FLC" (SSFLC) cell where the helix is unwound due to the strong interaction in thin cell. The director n of a molecule can be on either side of a cone with an opening angle of 2o and alternate each other by applying electrical field and vice versa. 9
Figure 1.7 The structure of the antiferroelectric smectic C* phase 11
Figure 1.8 Antiferroelectric-ferroelectric switching 11
Figure 1.9 Schematic illustration of the molecular orientational structures and the simulated light transmittance as function of electrical field in the three stable states. 13
Figure 1.10 (a) A three-component mixture of compound I, II and III with the mixing ratio of I:II:III=40:40:20, (b) the observed V-shaped switching (Upper) and the simulated light transmittance as a function of the normalized electrical field and (c) the simplified model of the phase with thresholdless antiferroelectricity. 15
Figure 1.11 Schematic representation of phases for non-chiral and chiral liquid crystal molecules. (a) Non-chiral molecules have only nematic (N) and isotropic (Iso) phases. (b) Chiral molecules exhibit a chiral nematic (N*) phase up to three blue phases and the isotropic phase. 17
Figure 1.12 Double twist cylinder found in blue phases. 18
Figure 1.13 Helical structure of the TGBA phase. 20
Figure 1.14 Transmittance versus electrical field obtained from compound HNP(10,0,2) at 74.9℃ in the SCA* phase on applying triangular wave 23
Figure 1.15 Schematic representation the molecular structure of the studied compounds. 24
Figure 2.1 The NMR spectra of MNP(0,2), HNP(0,2) and HNP(11,0,2). 33
Figure 2.2 Optical setup for the transmittance measurement, L, He-Ne laser; P, Polarizer; C, LC sample cell; D, Detector; F, Function generator; A, Power preamplifier; S, Digital oscilloscope. 43
Figure 3.1 Non-iridescent platelet texture of BPII phase obtained from HNP(8,0,2) under crossed polarizing microscope at 150.6℃. (magni-fication×200) 45
Figure 3.2 A scale-like or fan like texture of N* phase obtained from HNP(8,0,2) under crossed polarizing microscope at 148.0℃. (magni-fication×200) 45
Figure 3.3 A planar texture of N* phase obtained from HNP(8,0,2) in the 2 mm thickness of homogeneously aligned cell under crossed polarizing microscope at 137.1℃. (magnification×200) 46
Figure 3.4 A spiral filament texture of TGBA phase obtained from displayed a HNP(8,0,2) under crossed polarizing microscope at136.0℃. (magni-fication×200) 46
Figure 3.5 A Grandjean-like steps texture of TGBA* phase obtained from HNP(8,0,2) in the 5mm thickness of homogeneously aligned cell under crossed polarizing microscope at 136.0℃. (magnification×200) 48
Figure 3.6 Focal-conic and homeotropic texture of SA obtained from HNP(12,0,2) under crossed polarizing microscope at 124.6℃. (magni-fication×200) 48
Figure 3.7 Two kinds of textures in the SCA* phases obtained from HNP(12,0,2) under crossed polarizing microscope at 107.6℃ (magni-fication×200); (a) striated focal-conic, and (b) two brushes and four brushes defect in the pseudo-homeotropic texture 49
Figure 3.8 (a) The birefringence texture at 124.6℃, and (b) the parquet texture at 124.4℃ in the SA phase obtained from HNP(12,0,2) in homogeneous alignment cell with 2 mm thickness under crossed polarizing microscope. (magnification×200.) 50
Figure 3.9 The microscope striped pattern of the homogeneous texture in the SCA* phase obtained from HNP(12,0,2) under crossed polarizing microscope at 101.0℃ (a) before and (b) after switching of the electric field with ±1.0V. (magnification×200) 51
Figure 3.10 DSC thermogram for HNP(13,0,2) in heating and cooling runs at a scanning rate of 5℃/min scanning rate. 53
Figure 3.11 A plot of transition temperature on cooling process as a function of terminal aliphatic chain length for compounds HNP(p,0,2). 55
Figure 3.12 Switching behaviors in the SA phase at 110.0℃ (curve a), SCA* phase at 105.0℃ (curve b), 90.0 ℃(curve b), and 65℃ (curve c) obtained from HNP(12,0,2) in the homogeneous aligned cell with 2 mm thickness. 56
Figure 3.13 Magnitude of the spontaneous polarization plotted as a function of temperature for HNP(p,0,2). Tc is the temperature of SA-SCA* transition. 58
Figure 3.14 Temperature dependence of the dielectric constant e' of compound HNP(13,0,2) at 10kHz in the cell with 25 mm thickness. 59
Figure 3.15 Transmittance versus electrical field obtained from compound HNP(8,0,2) at several temperatures and frequencies in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 61
Figure 3.16 Transmittance versus electrical field obtained from compound HNP(9,0,2) at several temperatures and frequencies in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 62
Figure 3.17 Transmittance versus electrical field obtained from compound HNP(11,0,2) at several temperatures and 1Hz in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 64
Figure 3.18 Transmittance versus electrical field obtained from compound HNP(12,0,2) at several temperatures and 0.5Hz in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 65
Figure 3.19 Optical transmittance and switching current peaks as a function of applied electric field observed from HNP(12,0,2) at 0.5Hz , 100℃, in a 5 mm homogeneous cell. 66
Figure 3.20 Optical transmittance and switching current peaks as a function of applied electric field observed from HNP(12,0,2) at 0.5Hz , 80℃ in a 5 mm homogeneous cell. 68
Figure 3.21 Transmittance versus electrical field obtained from compound HNP(12,0,2) at several temperatures and 0.5Hz in the SCA* phase on applying triangular wave in a 2 mm homogeneous cell. 69
Figure 3.22 Transmittance versus electrical field obtained from compound HNP(13,0,2) at several temperatures and 1Hz in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 70
Figure 3.23 Transmittance versus electrical field obtained from compound HNP(14,0,2) at several temperatures and 1Hz in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 71
Figure 3.24 Transmittance versus electrical field obtained from compound HNP(13,0,2) at several temperatures and 1Hz in the SCA* phase on applying triangular wave in a 2 mm homogeneous cell. 73
Figure 3.25 A focal conic texture of N* phase obtained from HNP(11,1,2) under crossed polarizing microscope at 118.5℃.(magnification×200) 74
Figure 3.26 Two kinds of Textures in TGBA phase obtained from HNP(11,1, 2) under crossed polarizing microscope on cooling process. (a) The spiral filament texture (118.3℃, magnification×200), and (b) The vermis texture (118.3℃, magnification×200). 76
Figure 3.27 Textures of (a) N*→TGBA transition at 116.8℃, and (b) TGBA→SA transition at 116.5℃ obtained from HNP(12,1,2) in the 2 mm thickness of homogeneously aligned cell under crossed polarizing microscope. (magnification×200) 77
Figure 3.28 Focal-conic and homeotropic texture of SA obtained from HNP(12,1,2) under crossed polarizing microscope at 115.6℃. (magni-fication×200) 78
Figure 3.29 Two kinds of textures in the SCA* phases obtained from HNP(12,1,2) under crossed polarizing microscope at 108.5℃ (magni-fication×200); (a) broken focal-conic, and (b) two brushes and four brushes defect in the pseudo-homeotropic texture 79
Figure 3.30 DSC thermogram for HNP(12,1,2) in heating and cooling runs at a scanning rate of 5℃/min scanning rate. 81
Figure 3.31 DSC thermogram for HNP(12,1,2) near the clearing point in (a) heating and (b) cooling runs at a scanning rate of 0.3℃/min. 83
Figure 3.32 A plot of the transition temperature as function of the alkyl chain length (p) for HNP(p,1,2). 84
Figure 3.33 Switching behaviors in the SA phase and SCA* phase at 110.0℃(curve a), SCA* phase at 106.0℃ (curve b) and 103℃ (curve c) of HNP(10,1,2) in the homogeneous aligned cell with 2 mm thickness. 85
Figure 3.34 Magnitude of the spontaneous polarization plotted as a function of temperature for HNP(p,1,2). Tc is the temperature of SA-SCA* transition.. 87
Figure 3.35 Temperature dependence of the dielectric constant e' of compound HNP(10,1,2) at 10kHz in the cell with 25 mm thickness. 88
Figure 3.36 Frequency dependence of the dielectric dispersion curve (·) and absorption curve (o) of material HNP(10,1,2) in the SCA* phase at 100℃. 89
Figure 3.37 Transmittance versus electrical field obtained from compound HNP(9,1,2) at several temperatures 1Hz in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 91
Figure 3.38 Transmittance versus electrical field obtained from compound HNP(10,1,2) at several temperatures and 1Hz in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 92
Figure 3.39 Transmittance versus electrical field obtained from compound HNP(11,1,2) at several temperatures and 1Hz in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 94
Figure 3.40 Transmittance versus electrical field obtained from compound HNP(12,1,2) at several temperatures and 1Hz in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 95
Figure 3.41 Transmittance versus electrical field obtained from compound HNP(13,1,2) at several temperatures and 1Hz in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 96
Figure 3.42 Transmittance versus electrical field obtained from compound HNP(13,1,2) at several frequencies in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 97
Figure 3.43 Transmittance versus electrical field obtained from compound HNP(14,1,2) at several temperatures and 1Hz in the SCA* phase on applying triangular wave in a 5 mm homogeneous cell. 99
Figure 3.44 Transmittance versus electrical field obtained from compound HNP(14,1,2) at several temperatures and 1Hz in the SCA* phase on applying triangular wave in a 2 mm homogeneous cell. 100
Figure A.1 Switching behaviors in the SA phase at 95.0℃ (curve a), SCA* phase at 94.2℃ (curve b), and 90.0℃ (curve c) obtained from HNP(8, 0,2) in the homogeneous aligned cell with 2 mm thickness. 108
Figure A.2 Switching behaviors in the SA phase at 102.0℃ (curve a), SCA* phase at 100.5℃ (curve b), and 87.0℃ (curve c) obtained from HNP(9, 0,2) in the homogeneous aligned cell with 2 mm thickness. 109
Figure A.3 Switching behaviors in the SA phase at 105.0℃ (curve a), SCA* phase at 103.2℃ (curve b), and 70.0℃ (curve c) obtained from HNP (11,0,2) in the homogeneous aligned cell with 2 mm thickness. 110
Figure A.4 Switching behaviors in the SA phase at 107.0℃ (curve a), SCA* phase at 106.2℃ (curve b), and 80.0℃ (curve c) obtained from HNP (13,0,2) in the homogeneous aligned cell with 2 mm thickness. 111
Figure A.5 Switching behaviors in the SA phase at 110.0℃ (curve a), SCA* phase at 109.5℃ (curve b), and 75.0℃ (curve c) obtained from HNP (14,0,2) in the homogeneous aligned cell with 2 mm thickness. 112
Figure A.6 Temperature dependence of the dielectric constant e' for compound HNP(8,0,2) at 10kHz in the cell with 25 mm thickness. 113
Figure A.7 Temperature dependence of the dielectric constant e' for compound HNP(9,0,2) at 10kHz in the cell with 25 mm thickness. 114
Figure A.8 Temperature dependence of the dielectric constant e' for compound HNP(11,0,2) at 10kHz in the cell with 25 mm thickness. 115
Figure A.9 Temperature dependence of the dielectric constant e' for compound HNP(12,0,2) at 10kHz in the cell with 25 mm thickness. 116
Figure A.10 Temperature dependence of the dielectric constant e' for compound HNP(14,0,2) at 10kHz in the cell with 25 mm thickness. 117

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