臺灣博碩士論文加值系統

9-[N,N-di(4-carboxyphenyl)amino]anthracene是由對氟苯腈與9-蒽胺進行親核性取化反應生成腈基化合物，隨後此二腈中間物以鹼性水解而致使一新型含蒽胺的二羧酸單體化合物的產生。N-(4-Aminophenyl)phenothiazine是由對氟硝基苯與酚噻嗪進行親核性取代反應生成硝基化合物，接著再用聯胺與鉑金屬催化還原而被合成出。更進一步的與對氟硝基苯進行胺基化反應，隨後將二硝中間物還原而獲得一個新型含酚噻嗪的二胺單體化合物[4,4’-diamino-4”-N-phenothiazinyltriphenylamine]。
本論文分成三個部分，包含了以9-[N,N-di(4-carboxyphenyl)amino]anthracene為主體所合成出的二個系列新型含蒽胺之芳香族聚(胺-醯胺) 和聚(胺-1,3,4,-噁二唑)，以及第三個部分以4,4’-diamino-4”-N-phenothiazinyltriphenylamine為主體所合成出的一系列新型含酚噻嗪之芳香族聚(胺-醯胺)。這三個系列新型具蒽胺與酚噻嗪側鏈基團之芳香族高分子之合成與基本特性、光致發光、電化學及電致變色性質已被分別研究與比較。所有的高分子不僅在極性非質子型溶劑中有好的溶解性，出色的薄膜成形能力，高的玻璃轉換溫度、軟化溫度、好的熱穩定性、較低的HOMO能階，而且部分高分子也展現好的光致發光及出色可逆的電致變色特性。如此，這些含蒽胺的新型高分子由於適當的HOMO值和出色熱穩定性、螢光量子效率及電化學不僅能被做為P-LED的電洞傳輸層和綠色發光材料，而且也可應用於新型的電致變色元件；這些含酚噻嗪的高分子由於適當的HOMO值和出色的電化學及熱穩定性也許能被廣泛的應用在P-LED當電洞傳輸層和電致變色的材料。

The newly anthrylamine-based aromatic dicarboxylic acid, 9-[N,N-di(4-carboxyphenyl)amino]anthracene, was successfully synthesized by the sodium hydride-mediated condensation of 9-aminoanthracene with 4-fluorobenzonitrile, followed by the alkaline hydrolysis of the dinitrile intermediate led to a newly anthrylamine-based aromatic dicarboxylic acid. N-(4-Aminophenyl)phenothiazine was prepared by the cesium fluoride-mediated aromatic nucleophilic substitution reaction of phenothiazine with 4-fluoronitrobenzene followed by hydrazine Pd/C-catalytic reduction. Further amination reaction between N-(4-aminophenyl)phenothiazine with 4-fluoronitrobenzene, subsequent reduction of the dinitro intermediate obtained to the new phenothiazine-containing aromatic diamine, 4,4’-diamino-4”-N-phenothiazinyltriphenylamine.
This study has been separated into three parts. Part I and II include two series of novel aromatic poly(amine-amide)s and poly(amine-1,3,4-oxadiazole)s based on 9-[N,N-di(4-carboxyphenyl)amino]anthracene. Part III included a series of novel aromatic poly(amine-amide)s based on 4,4’-diamino-4”-N-phenothiazinyltriphenylamine. The synthesis, basic characterization, photoluminescence, electrochemical and electrochromic properties of three series of novel aromatic polymers bearing pendent anthrylamine and phenothiazine groups were investigated and compared, respectively. All polymers had good solubility in many polar aprotic solvents, and exhibited excellent thin-film-forming ability. In additional to high Tg or Ts values, good thermal stability, and lower HOMO energy levels, some of polymers also exhibited good photoluminescent and excellent reversibility of electrochromic characteristics. Thus, these novel anthrylamine-containing polymers can be considered not only as hole-transporting layer and green light-emitting materials in P-LED but also could be widely applied as a new electrochromic devices due to their proper HOMO values, excellent thermal stability, fluorescence quantum efficiency and good electrochemical behavior; these phenothiazine-containing polyamides may be widely applied in P-LED as hole-transporting layer and electrochromic materials due to their proper HOMO values, excellent electrochemical and thermal stability.

PART I

Novel Thermally Stable Triarylamine-Containing Aromatic Polyamides
Bearing Anthrylamine Chromophores for
Highly Efficient Green-Light-Emitting Materials

ABSTRACT OF PART I 2
CHAPTER1 INTRODUCTION 3
CHAPTER 2 EXPERIMENTAL SECTION 6
2.1. Materials 6
2.2. Monomer Synthesis 6
2.2.1. 9-Nitroanthracene (1) 6
2.2.2. 9-Aminoanthracene (2) 7
2.2.3. 9-[N,N-Di(4-cyanophenyl)amino]anthracene (3) 8
2.2.4. 9-[N,N-Di(4-carboxyphenyl)amino]anthracene (4) 9
2.3. Polymer Synthesis 10
2.4. Preparation of the Films 11
2.5. Measurements 11
CHAPTER 3 RESULTS AND DISCUSSION 14
3.1. Mononer Synthesis 14
3.2. Polymer Synthesis 24
3.3. Polymer Properties 31
3.3.1. Basic Characterization 31
3.3.2. Thermal Properties 33
3.3.3. Optical Properties 36
3.3.4. Solvatochromism 40
3.3.5. Electrochemical Properties 43
3.3.6. Spectroelectrochemical Studies 50
CHAPTER 4 CONCLUSIONS 52
REFERENCES AND NOTES 53



PART II

Cathodic Red Electrochromic Aromatic Poly(amine-1,3,4-oxadiazole)s Bearing Anthrylamine Chromophores: Synthesis and Photophysical, Electrochemical and Electrochromic Properties

ABSTRACT OF PART II 56
CHAPTER 1 INTRODUCTION 57
CHAPTER 2 EXPERIMENTAL SECTION 61
2.1. Materials 61
2.2. Polymer Synthesis 61
2.3. Film Preparation and Cyclodehydration of the Hydrazide Polymers 62
2.4. Measurements 62
CHAPTER 3 RESULTS AND DISCUSSION 65
3.1. Polymer Synthesis 65
3.2. Polymer Properties 70
3.2.1. Basic Characterization 70
3.2.2. Thermal Properties 72
3.2.3. Optical Properties 75
3.2.4. Electrochemical Properties 79
3.2.5. Electrochromic Characteristics 84
CHAPTER 4 CONCLUSIONS 87
REFERENCES AND NOTES 88



PART III

Highly Efficiently Anodic Purple Electrochromic Polymers Bearing Pendent Phenothiazine Redox Units: Synthesis and Characterization

ABSTRACT OF PART III 92
CHAPTER 1 INTRODUCTION 93
CHAPTER 2 EXPERIMENTAL SECTION 96
2.1. Materials 96
2.2. Monomer Synthesis 96
2.2.1. N-(4-Nitrophenyl)phenothiazine (1) 96
2.2.2. N-(4-Aminophenyl)phenothiazine (2) 97
2.2.3. 4,4’-Dinitro-4”-N-phenothiazinyltriphenylamine (3) 98
2.2.4. 4,4’-Diamino-4”-N-phenothiazinyltriphenylamine (4) 99
2.3. Polymer Synthesis 100
2.4. Film Preparation 101
2.5. Measurements 101
CHAPTER 3 RESULTS AND DISCUSSION 104
3.1. Mononer Synthesis 104
3.2. Polymer Synthesis 112
3.3. Polymer Properties 118
3.3.1. Basic Characterization 118
3.3.2. Thermal Properties 120
3.3.3. Optical Properties 123
3.3.4. Electrochemical Properties 126
3.3.5. Electrochromic Characteristics 129
CHAPTER 4 CONCLUSIONS 134
REFERENCES AND NOTES 135



Appendix 138
Curriculum Vitae 138
List of Publications 139
Journal Papers 139
Conference papers 140
Research Creativity Award (in Chinese) 141
Research Creativity Award (in English) 142

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