臺灣博碩士論文加值系統

近年來許多文獻指出旋光中心末端基對液晶材料影響十分顯著，因此本研究以(S)-propylene oxide為起始物和醇類在鹼性條件下合成四系列液晶化合物，探討藉著改變液晶材料的分子結構上的非旋光末端烷鏈長度(m)及旋光末端烷鏈長度(n)對液晶相光電性質的影響。液晶材料的液晶相及相轉移溫度是由偏光紋理圖、DSC來鑑定。
實驗結果顯示:四系列化合物都具SmA*和SmC*相的生成,在第一系列液晶材料中I(m=8-12, n=5)中SmA*相的溫度範圍隨著非旋光末端烷鏈的增長而更窄,此外澄清點溫度隨著旋光末端烷鏈的增長而降低。
材料的物理性質如電流轉換行為、自發性極化值、傾斜角、和介電常數皆於誘電性SmC*液晶相下量測。四系列化合物I(m=8-12, n=5)、II(m=8-12, n=6)、III(m=8-12, n=7)和IV(m=8-12, n=8) 的自發性極化的最大值範圍介於7.84-12.71 nC/cm2。四系列化合物自發極化的最大值隨著旋光末端烷鏈的增長而降低，與化合物PPmPPn(m=8-12, n=1-4)比較之下，其自發極化最大值卻隨著旋光末端烷鏈的增長而增加。前者推測原因為加長旋光末端烷鏈增加了旋光末端基的重量,抑制了旋光中心上的偶極，使得自發性極化值降低。而後者原因為增加旋光末端烷鏈時使得烷鏈跟旋光中心需要花較長的時間沿躺在分子長軸上，而旋光中心的偶極被固定在同一方向上，使得自發極化值增加。四系列化合物I(m=8-12, n=5)、II(m=8-12, n=6)、III(m=8-12, n=7)和IV(m=8-12, n=8)的傾斜角最大值範圍分別介於16.4-32.0°，結果顯示四系列化合物之傾斜角最大值隨著非旋光末端烷鏈的增長而增加，而旋光末端烷鏈長度的改變與傾斜角無顯著的影響。
總而言之，以(S)-1-alkyloxy-2-propanols 作為基楚架構液晶材料已經成功的被合成。而四系列液晶材料皆顯示有雙向型的SmA*向和SmC*相。並且,依非旋光及旋光末端烷鏈長度誘電性液晶相之間的關係已被建立,此結果在學術上提供給後續誘電性液晶材料的設計與合成方面的參考。

The purpose of this research work was an attempt to elucidate the extension of chiral alkyl length of liquid crystal materials possessing the lateral methyl substituent affects on the mesomorphic and electro-optical properties. Thus, new chiral precursors, (S)-1-alkyloxy-2-propanols were designed and synthesized by the reaction of (S)-propylene oxide with alkanols under basic condition. Subsequently, four homologous series of chiral liquid materials, (R)-1-alkyloxy-2-propyl 4-[4’-(4”-alkyloxyphenyl)phenyloxy]benzoates , I(m=8-12,n=5), II(m=8-12,n=6), III(m=8-12,n=7) and IV(m=8-12,n=8), were designed and synthesized to investigate the effect of changing aliphatic alkyl chain length (m) and chiral alkyl chain length (n) on the mesomorphic and electro-optical properties.
The mesomorphic phases and their corresponding transition temperatures were primarily characterized by the microscopic textures and DSC thermograms, and the ferroelectric phase were further identified by the measurements of electric switching behavior and dielectric constant ε'.
The results show that all chiral liquid materials display enantiotropic SmA* phase and SmC* phase. The results also show that compounds with shorter alkyl chain (m=8-10) exhibit a phase sequence of Iso.-SmA*-SmC*- Cr1-Cr2, while compounds (m=11, 12) with longer chain exhibit a phase sequence of Iso.-SmA*-SmC*-Cr in cooling process. With the increasing achiral terminal chain lengths, m, the clearing point decrease. The temperature range of the SmA* phase decreases by extending the length of achiral aliphatic chains in a series of compounds I-6(m=8-12, n=5).
The physical properties such as switching current, spontaneous polarization, tilt angle and dielectric constant in the ferroelectric SmC* phases of the chiral compounds were measured. In general, the magnitudes of spontaneous polarization ascend with decreasing temperature. The maximum magnitudes of the spontaneous polarization for these compounds are approximately in a range of 7.84-12.71 nC/cm2. Comparison of compounds I, II, III, IV(m=8-12, n=5-8) and PPmPPn(m=8-12, n=1-4) clearly show that the maximum Ps value is increased by extending the length (n) of the alkyl chains at chiral tail from n=1, 2, 3 to 4, but that is decreased by extending the length (n) of the alkyl chains at chiral tail from n=5, 6, 7 to 8. The former results are due to, as the alkyl chain is extended, the chiral center and a certain portion of the alkyl chain are supposed to spend more time lying along the long axis of the molecule, such that the chiral center has a fixed spatial arrangement with respect to its local environment, this in tern will fix the orient of the diple at the chiral center. The later results are presumably due to the effect of increasing mass that shield the dipole at the chiral centre and then reduce the Ps.
The maximum tilt angles of compounds are approximately in a range of 16.4-32.00. The magnitudes of apparent tilt angle (θ) values are increased by extending achiral terminal alkyl chain length(m), but that has no significant correlation with the chiral terminal alkyl chain length (n).
In conclusion, the optically active alcohols, (S)-1-alkyloxy-2-propanols for the use as the building blocks of the chiral liquid crystals were designed and synthesized. Four series of chiral materials derived from these alcohols exhibit enantiotropic SmA* and SmC* phases. The structure-property correlation of these chiral materials in terms of achiral and chiral alkyl chain lengths (m and n) are established, herein.

ENGLISH ABSTRATE III
中文摘要 V
ACKNOWLEDGEMENTS VI
TABLE OF CONTENTS VII
LIST OF SCHEME XIII
LIST OF FIGURES XIV
CHAPTER 1
INTRODUCTION 1
1.1. Overview 1
1.2. Chiral smectic phases 4
1.2.1 Chiral smetic A phase 4
1.2.2. Chiral smetic C phase (ferroelectric phase) 5
1.3. Motivation of study 11
CHAPTER 2
EXPERIMENTAL 15
2.1. Preparation of Materials 15
2.1.1. Synthesis of 4-(4’-alkoxyphenyl)benzoic acid, 1(m=8-12) 17
2.1.2. Synthesis of 4-[(methoxycarbonyl)oxy]benzoic acid,2 17
2.1.3. Synthesis of (S)-1-pentyloxy-2-propanol, I-3 18
2.1.4. Synthesis of (S)-1-hexyloxy-2-propanol, II-3, (S)-1-heptyloxy-2-propanol, III-3 and (S)-1-octyloxy-2-propanol, IV-3 18
2.1.5. Synthesis of (R)- 1-methyl-2-(pentyloxy)ethyl 4- (methoxycarbonyloxy)
benzoate 19
2.1.6. Synthesis of (R)-1-methyl -2-(hexyloxy)ethyl 4-[(methoxycarbonyl)oxy]
benzoate, II-4, (R)-1-methyl-2-(heptyloxy)ethyl 4-[(methoxycarbonyl)oxy]
benzoate ,III-4 and (R)- 1-methyl-2-(octyloxy)ethyl 4-[(methoxycarbonyl)oxy]
benzoate,IV-4 19
2.1.7. Synthesis of (R)-1-methyl-2-(pentyloxy)ethyl 4-hydroxybenzoate, I-5 20
2.1.8. Synthesis of (R)-1-methyl-2-(hexyloxy)ethyl 4-hydroxybenzoate, II-5, (R)- 1-methyl-2-(heptyloxy) ethyl 4-hydroxybenzoate, III-5 and (R)-1-methyl -2-octyloxy ethyl 4-hydroxybenzoate, IV-5 20
2.1.9. Synthesis of (R)-1-pentyloxy-2-propyl 4-[4’-(4”-alkyloxyphenyl)phenyloxy]
benzoates, I-6 21
2.1.10. Synthesis of (R)-1-hexyloxy-2-propyl 4-[4’-(4”-alkyloxyphenyl)phenyloxy]
benzoates, II-6 22
2.1.11. Synthesis of (R)-1-heptyloxy-2-propyl4-[4’-(4”-alkyloxyphenyl)phenyloxy]
benzoates, III-6 22
2.1.12. Synthesis of (R)-1-octyloxy-2-propyl 4-[4’-(4”-alkyloxyphenyl)phenyloxy]
benzoates, IV-6 22
2.2. Characterization of Materials 23
2.2.1. Chemical structure identification 23
2.2.2. Masophase identification 23
2.2.3. The spontaneous polarization (Ps) measurement 23
2.2.4. Measurements of switching behavior 26
2.2.5. Dielectric constant measurement 26
2.2.6. Optical tilt angle measurement 27
CHAPTER 3
RESULTS AND DISCUSSION 29
3.1. Chemical structure identification 29
3.2. The effect of peripheral chain length on the mesomorphic properties of compounds I-6(m=8-12, n=5) 29
3.2.1. Mesomorphic phase studies for the compounds I-6(m=8-12) 30
3.2.2. Differential scanning calorimetric (DSC) studies for the compounds I-6(m=8-12, n=5) 32
3.2.3. Switching current behavior studies for the compounds I-6(m=8-12, n=5) 36
3.2.4. Dielectric property measurements for the compounds I-6(m=8-12, n=5) 37
3.2.5. Spontaneous polarization (Ps) measurements for the compounds I-6(m=8-12, n=5) 38
3.2.6. The optical tilt angle (θ) measurements for the compounds I-6(m=8-12) 38
3.3. The effect of peripheral chain length on the mesomorphic properties of compounds II-6(m=8-12, n=6) 40
3.3.1. Mesomorphic phase studies for the compounds II-6(m=8-12, n=6) 40
3.3.2. Differential scanning calorimetric (DSC) studies for the compounds II-6(m=8-12, n=6) 42
3.3.3. Switching current behavior studies for the compounds II(m=8-12, n=6) 46
3.3.4. Dielectric property measurements for the compounds II(m=8-12, n=6) 47
3.3.5. Spontaneous polarization (Ps) measurements for the compounds II-6(m=8-12, n=6) 48
3.3.6. The optical tilt angle (θ) measurements for the compounds II-6(m=8-12, n=6) 48
3.4. The effect of peripheral chain length on the mesomorphic properties of compounds
III-6(m=8-12, n=7 50
3.4.1. Mesomorphic phase studies for the compounds III-6(m=8-12, n=7) 50
3.4.2. Differential scanning calorimetric (DSC) studies for the compounds III-6(m=8-12) 52
3.4.3. Switching current behavior studies for the compounds III-6(m=8-12, n=7) 57
3.4.4. Dielectric property measurements for the compounds III-6(m=8-12, n=7) 59
3.4.5. Spontaneous polarization (Ps) measurements for the compounds III-6(m=8-12, n=7) 60
3.4.6. The optical tilt angle (θ) measurements for the compounds III-6(m=8-12, n=7 60
3.5. The effect of peripheral chain length on the mesomorphic properties of compounds IV-6(m=8-12, n=8) 62
3.5.1. Mesomorphic phase studies for the compounds IV-6(m=8-12, n=8 62
3.5.2. Differential scanning calorimetric (DSC) studies for the compounds IV-6(m=8-12, n=8) 63
3.5.3. Switching current behavior studies for the compounds IV-6(m=8-12, n=8) 68
3.5.4. Dielectric property measurements for the compounds IV-6(m=8-12, n=8) 69
3.5.5. Spontaneous polarization (Ps) measurements for the compounds IV-6(m=8-12, n=8 70
3.5.6. The optical tilt angle (θ) measurements for the compounds IV-6(m=8-12, n=8 71
3.6. Comparison of mesomorphic property, spontaneous polarization, and optical tilt angle for I-6(m=8-12, n=5), II-6(m=8-12, n=6), III-6(m=8-12, n=7), IV-6(m=8-12, n=8) and PPmPPn(m=8-12, n=1-4) 73
3.6.1. Mesomorphic property 73
3.6.2. Spontaneous polarization (Ps) 74
3.6.3. The optical tilt angle (θ) 76
3.7. Comparison of spontaneous polarization for II-6(m=8, n=6) and MHPOBC 77
CHAPTER 4
CONCLCUSIONS 78
LIST OF SCHEME
Scheme 1. Synthetic procedures for the target compounds I-6(m=8-12, n=5), II-6(m=8-12, n=6), III-6(m=8-12, n=7) and IV(m=8-12, n=8 16
LIST OF TABLES
Table 3.2.1. The transition temperatures T(℃) and enthalpiesΔH (KJ/mol) of the transition for the materials I-6(m=8-12, n=5) measured by DSC at 5　℃/min scanning rate on cooling stage 34
Table 3.3.1. The transition temperatures T(℃) and enthalpiesΔH(KJ/mol) of the transition for the materials II-6(m=8-12, n=6) measured by DSC at 5℃/min scanning rate on cooling stage 45
Table 3.4.1. The transition temperatures T(℃) and enthalpiesΔH(KJ/mol) of the transition for the materials III-6(m=8-12, n=7) measured by DSC at 5℃/min scanning rate on cooling stage 55
Table 3.5.1. The transition temperatures T(℃) and enthalpiesΔH(KJ/mol) of the transition for the materials IV-6(m=8-12) measured by DSC at 5℃/min scanning rate on cooling stage 66
LIST OF FIGURES
Figure1.1. The melting process of a calamitic (rod-like) liquid-crystalline material 2
Figure1.2. Placement of the liquid crystal phase within the general scheme of the common states of matter. Two basic group of liquid crystals are distinguished: lyotropic phases, which form as a function of concentration c in the present of an isotropic solvent; and thermotropic phases, which are observed by variation of temperature T. Thermotropic phases are further classified according to their basic molecular shaped: rod-like (calamitic), disk-like (discotic), and lath-like (sanidic) 2
Figure1.3. The structure of the smectic A phase (SmA*) 4
Figure1.4. Symmetry operations in the smectic C phase and chiral smectic C* phase (SmC*) 6
Figure1.5. Helical macrostructure of the chiral smectic C* phase 7
Figure1.6. Schematic representation of a "surface stabilized FLC" (SSFLC) cell where the helix is unwound due to the strong interaction in thin cell. The director of a molecule can be on either side of a cone with an opening angle of 2θ and alternate each other by applying electrical field and vice versa 8
Figure1.7. A surface stabilized ferroelectric liquid crystal devices SSFLCD: schematic of the cell possessed two states 9
Figure2.1. Block diagram for the measure circuit 25
Figure2.2. Schematic illustrations for the current induced by applying a field with a triangular form 25
Figure2.3. Schematic illustrations for the measurement of the apparent tilt angle….28
Figure3.2.1. Microphotographic textures of the mesomorphic phases obtained from I-6(m=11, n=5) (a) the SmA* phase was characterized by the formation of focal conic texture (b) the SmC* phase by the formation of striated focal conic texture (magnification
× 400) 31
Figure 3.2.2. DSC thermogram for I-6(m=12, n=5) on heating and cooling runs at a scanning rate of 5/min 33
Figure3.2.3. A plot of transition temperature as a function of achiral terminal aliphatic chain length “m” for compounds I-6(m=8-12, n=5) on cooling process 35
Figure3.2.4. The switching current behavior of I-6(m=8, n=5) obtained at 10Hz and several temperature on applying triangle wave in 2 μm homogeneous aligned cell. 36
Figure 3.2.5. Temperature dependence of the dielectric constant ε' for I-6(m=8, n=5) at 100Hz in the cell with 25 μm thickness under 1℃/min cooling process 37
Figure3.2.6. Magnitudes of the spontaneous polarization plotted as a function of temperature for I-6(m=8-12, n=5). Tc is the transition temperature of SmA* phase to SmC* phase 39
Figure3.2.7. Optic-tilt angle plotted as a function of temperature for I-6(m=8-12, n=5). Tc is the transition temperature of the SmA* phase to SmC* phase 39
Figure3.3.1. Microphotographic textures of the mesomorphic phases obtained from II-6(m=10, n=6) (a) the SmA* phase was characterized by the formation of a focal-conic texture (b) the SmC* phase by the formation of striated focal-conic texture (magnification × 400) 41
Figure 3.3.2. DSC thermogram for II-6(m=10, n=6) on heating and cooling runs at a scanning rate of 5℃/min 43
Figure 3.3.3. A plot of transition temperature as a function of achiral terminal aliphatic chain length “m” for compounds II-6(m=8-12, n=6) on cooling process 44
Figure 3.3.4. The switching current behavior of II-6(m=8, n=6) obtained at 10Hz and several temperature on applying triangle wave in 2 μm homogeneous aligned cell 46
Figure 3.3.5. Temperature dependence of the dielectric constant ε' for II-6(m=9, n=6) at 100Hz in the cell with 25 μm thickness under 1℃/min cooling process 47
Figure 3.3.6. Magnitudes of the spontaneous polarization plotted as a function of temperature for II-6(m=8-12, n=6). Tc is the transition temperature of SmA* phase to SmC* phase 49
Figure 3.3.7. Optic-tilt angle plotted as a function of temperature for II-6(m=8-12, n=6). Tc is the transition temperature of the SmA* phase to SmC* phase 49
Figure 3.4.1. Microphotographic textures of the mesomorphic phases obtained from III-6(m=12, n=7) (a) the SmA* phase was characterized by the formation of a focal-conic texture (b) the SmC* phase of observed from the striated focal-conic texture (c) the Crystal phase (magnification × 400) 52
Figure 3.4.2. DSC thermogram for III-6(m=8, n=7) on heating and cooling runs at a scanning rate of 5℃/min 54
Figure 3.4.3. A plot of transition temperature as a function of achiral terminal aliphatic chain length “m” for compounds III-6(m=8-12, n=7) on cooling process 56
Figure 3.4.4. The switching current behavior of III-6(m=10, n=7) obtained at 20Hz and several temperature on applying triangle wave in 2 μm homogeneous aligned cell 58
Figure 3.4.5. Temperature dependence of the dielectric constant ε' for III-6(m=9, n=7) at 100Hz in the cell with 25 μm thickness under 1℃/min cooling process 59
Figure 3.4.6. Magnitudes of the spontaneous polarization plotted as a function of temperature for III-6(m=8-12, n=7). Tc is the transition temperature of SmA* phase to SmC* phase 61
Figure 3.4.7. Optic-tilt angle plotted as a function of temperature for III-6(m=8-12, n=7). Tc is the transition temperature of the SmA* phase to SmC* phase 61
Figure3.5.1. Microphotographic textures of the mesomorphic phases obtained from IV-6(m=11, n=8) (a) the SmA* phase was characterized by the formation of a focal-conic texture (b) the SmC* phase by the formation of striated focal-conic texture (magnification × 400) 64
Figure 3.5.2. DSC thermogram for IV-6(m=8, n=8) on heating and cooling runs at a scanning rate of 5℃/min 65
Figure3.5.3. A plot of transition temperature as a function of achiral terminal aliphatic chain length “m” for compounds IV-6(m=8-12, n=8) on cooling process 67
Figure3.5.4. The switching current behavior of IV-6(m=8, n=8) obtained at 20Hz and several temperature on applying triangle wave in 2 μm homogeneous aligned cell 68
Figure3.5.5. Temperature dependence of the dielectric constant ε＇ for IV-6(m=11, n=8) at 100Hz in the cell with 25 μm thickness under 1℃/min cooling process 69
Figure3.5.6. Magnitudes of the spontaneous polarization plotted as a function of temperature for compounds IV-6(m=8-12, n=8). Tc is the transition temperature of SmA* phase to SmC* phase 72
Figure3.5.7. Optic-tilt angle plotted as a function of temperature for IV-6(m=8-12, n=8). Tc is the transition temperature of the SmA* phase to SmC* phase 72
Figure 3.6.1 A plot of transition temperature as a function of the chiral terminal alkyl chain length “n” for chiral materials on cooling process 74
Figure3.6.2 (a) Magnitudes of the spontaneous polarization plotted as a function of temperature for compounds PPmPPn(m=10, n=1-4). Tc is the transition temperature of the SmA* phase to SmC* phase 76
Figure 3.6.3. (b) Magnitudes of the spontaneous polarization plotted as a function of temperature for compounds I-6(m=10, n=5), II-6(m=10, n=6), III-6(m=10, n=7), and IV-6(m=10, n=8). Tc is the transition temperature of the SmA* phase to SmC* phase 76

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