Morphology and Photophysical Properties of Conjugated Polymer Nanoparticles Based on Rapid Precipitation and Self-Assembled π-Conjugated Systems

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研究生：	Alis Godana Alis Godana
論文名稱：	Morphology and Photophysical Properties of Conjugated Polymer Nanoparticles Based on Rapid Precipitation and Self-Assembled π-Conjugated Systems Morphology and Photophysical Properties of Conjugated Polymer Nanoparticles Based on Rapid Precipitation and Self-Assembled π-Conjugated Systems
指導教授：	游進陽 Chin-Yang Yu
口試委員:	游進陽 Chin-Yang Yu 陳志堅 Jyh-Chien Chen 王丞浩 Chen-Hao Wang 趙基揚 Chi-Yang Chao 堀江正樹 Masaki Horie
學位類別：	博士 Doctor
系所名稱：	工程學院 - 材料科學與工程系 Department of Materials Science and Engineering
論文出版年：	2019
畢業學年度：	107
語文別：	英文
論文頁數：	142
中文關鍵詞：	carbazole 、conjugated polymer 、diphenylamine 、fluorene 、nanoparticle 、triethylene glycol side chains 、self-organization 、sheet-like structures
外文關鍵詞：	carbazole, conjugated polymer, diphenylamine, fluorene, nanoparticle, triethylene glycol side chains, self-organization, sheet-like structures
相關次數：	點閱：261 下載：0
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本論文利用奈米沉澱與分子自組裝製備共軛高分子。第一部分利用鈴木偶合反應合成出含芴—二苯胺、芴—咔唑(2,7位)、芴—咔唑(3,6位)等三種交替共軛高分子。由SEM觀察得知，這三種高分子的奈米尺寸介於35-65奈米之間。由吸收光譜發現，芴—二苯胺與芴—咔唑(2,7位)其水溶液分散狀態，與在THF溶劑中相比，具有藍位移的現象。由放射光譜發現，水溶液分散狀態芴—咔唑(2,7位)、芴—咔唑(3,6位)相較於THF溶劑中，具有約7nm的紅位移。而量子產率在這三種高分子中，從THF溶液至水溶液分散的過程中，都有降低的現象。第二部分利用鈴木偶合反應合成出芴—二苯胺之高分子，並探討其側鏈為疏水基團辛基烷和親水基團三乙二醇之自組裝現象。在THF/MeOH與THF/Acetone系統中由SEM及XRD發現，其形貌為晶形；在水中為非晶形結構。另外，在水溶液中的放射光譜相較於有機溶劑中具有紅位移的現象。

The design and synthesis of novel -conjugated materials is still an attractive research field due to their interesting optoelectronic properties, which make them potential candidates in various applications such as light emitting devices, solar cells and sensors. We have prepared conjugated polymer nanoparticles using rapid precipitation and self-assembled method. Self-assembly refers to the process by which nanoparticles or other discrete components spontaneously organize due to direct specific interactions, or indirectly, through their environment. Rapid precipitation was prepared by rapid injection of conjugated polymer (good solvent) solution into poor solvent under sonication. This dissertation is organized based on two independent sections.
In the first section, novel conjugated polymers containing fluorenes, PEGylated carbazoles and diphenylamines were synthesized by the palladium catalyzed Suzuki-Miyaura cross-coupling reaction. The dimensions of the conjugated polymer nanoparticles were in a range of 35–65 nm as observed by SEM analysis. A blue-shifted absorption of the conjugated polymer nanoparticles containing fluorenes and diphenyl amines or 2,7-linked carbazoles was observed compared to that of the polymer solution, this can be attributed to aggregation-induced disorder. The emission of the polymer nanoparticles containing fluorenes and carbazoles is red-shifted and this can be attributed to the increase in interchain interactions possibly due to conjugated polymer chains collapsing in water during nanoparticle formation. For all polymers, the decreases in emission quantum yields on going from polymer solution to nanoparticle dispersion were reflected the aggregation of the polymer chains in aqueous media.
In the second section, we synthesized conjugated copolymers containing fluorene and diphenylamine moieties containing octyl and triethylene glycol side chains via Suzuki-Miyaura cross-coupling reaction and their structures have been characterized. Conjugated polymer nanoparticles and self-organization of the polymers have been prepared by rapid precipitation and solvent diffusion methods, respectively. The morphologies of the conjugated polymers exhibited well-defined spherical amorphous structures and crystalline microspheres with the diameter ranging from several nanometer to micrometer. Self-assembled conjugated polymer aggregates were obtained in a selective good solvent/ poor solvent mixture. The emission maximum of the dispersed polymers in water was significantly red-shifted with dramatically reducing the photoluminescence quantum yield in comparison with those polymers in good solvents. In addition, the emission maximum of the self-assembled copolymers was barely red shifted with slightly decreasing the photoluminescence quantum yield.

Abstract    iii
Acknowledgments    v
List of Table    x
List of Figure    xi
List of Scheme    xiii
Appendix    xiv
Chapter 1: Introduction    1
Chapter 2: Background and literature review    4
1. Conjugated polymer nanoparticles and preparation methods    4
2. Backbone constructions and side chain modifications    6
3. Biological applications of conjugated polymer nanoparticle    9
3.1. Conjugated polymer nanoparticle for sensing and imaging    10
3.2. Conjugated polymer nanoparticle for drug delivery systems    14
4. Organic electronics    15
4.1. Organic solar cell    18
4.2. Organic light emitting devices    22
4.3. Optical sensors    24
5. Self-assembly of conjugated polymer    27
5.1. Organic electronics of self-assemblies    28
5.2. Supramolecular organic light emitting devices    28
5.3. Self-assembled nanomaterials for biomedical applications    29
5.4. Polymer micelles as drug delivery systems    30
5.5. Self-assembled nanomaterials for environmental sciences    31
6. Controlled and directed self-assembly    32
Chapter 3. Research Objectives    34
1. General objective    34
2. Specific objectives    34
Chapter 4: Experimental section and characterization    36
1. General considerations    36
2. Chemicals    38
3. Instruments    39
4. Synthesis of monomers    39
5. Polymerization and nanoparticle preparation    43
 Chapter 5: Conjugated Polymer Nanoparticles Based on Fluorenes, PEGylated Carbazoles and Diphenylamines    45
1. Introduction    45
2. Results and Discussion    48
2.1. Characterization of polymers by NMR spectroscopy    49
2.2. Molecular weights of polymers    51
2.3. Nanoparticle preparation and characterization    52
2.4. Photophysical properties of copolymers    54
2.5. Thermal properties    57
2.6. Electrochemical properties of polymers    58
3. Summary    59
Chapter 6: Fluorescent Conjugated Polymer Nanoparticles and Aggregates Based on Rapid Precipitation and Self-Assembled π-Conjugated Systems    60
1. Introduction    60
2. Experimental section    62
3. Results and discussion    67
3.1. Characterization of polymers by NMR spectroscopy    68
3.2. Conjugated polymer nanoparticles and aggregates    71
3.3. Photophysical properties of the copolymers    74
4. Summary    77
Chapter 7: Conclusion and Outlook    78
1. Conclusion    78
2. Outlook    78
Reference    80
Appendix    111

                                

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