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研究生:賴侑成
研究生(外文):You-Cheng Lai
論文名稱:水溶性螢光共軛高分子作為具有氣體響應性的自組裝奈米粒子應用於生物成像
論文名稱(外文):Water-soluble Fluorescent Conjugated Polymers as Self-assembled Nanoparticles with Gas-responsiveness for Biological Imaging
指導教授:鄭智嘉
指導教授(外文):Chih-Chia Cheng
口試委員:邱文英謝永堂張雍蔡協致戴子安
口試委員(外文):Wen-Yen ChiuYeong-Tarng ShiehYung ChangHsieh-Chih TsaiChi-An Dai
口試日期:2019-07-19
學位類別:碩士
校院名稱:國立臺灣科技大學
系所名稱:應用科技研究所
學門:自然科學學門
學類:其他自然科學學類
論文種類:學術論文
論文出版年:2019
畢業學年度:107
語文別:中文
論文頁數:168
中文關鍵詞:三級胺基團生物影像氣體響應性水溶性共軛高分子聚噻吩
外文關鍵詞:tertiary amine functional groupbiological imaginggas-responsivenesswater-soluble conjugated polymerspolythiophene
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摘要 i
Abstract ii
致謝 iii
目錄 iv
表目錄 viii
圖目錄 ix
第一章 緒論 1
1.1研究背景 1
1.2研究動機 3
第二章 文獻回顧 6
2.1水溶性共軛高分子(Water-soluble conjugated polymer) 6
2.1.1共軛高分子概述 6
2.1.2水溶性共軛高分子概述及發展近況 8
2.1.3雙親性共軛共聚高分子 13
2.2水溶性聚噻吩(Water-soluble polythiophene) 16
2.2.1水溶性聚噻吩概述 16
2.2.2聚噻吩聚合方式 20
2.2.3噻吩聚合物奈米粒子形成方式 27
2.3刺激應答(Stimuli-Responsivenesss) 29
2.3.1刺激應答概述 29
2.3.2 CO2刺激響應的官能基團 32
2.4生物影像(Biological image) 36
2.4.1生物成像概述 36
2.4.2螢光成像發展 37
2.4.3水溶性共軛高分子生物成像應用 39
2.5文獻回顧總結 42
第三章 實驗材料與方法 43
3.1研究設計 43
3.2實驗材料 44
3.2.1實驗藥品 44
3.2.2實驗溶劑 47
3.2.3細胞實驗材料 49
3.2.4相關實驗材料 51
3.3實驗儀器與設備參數 52
3.3.1旋轉塗佈機(Spin Coaters) 52
3.3.2桌上型酸鹼度計(pH Meter) 52
3.3.3酵素免疫分析儀(ELISA Reader) 53
3.3.4元素分析儀(elementar vario EL cube) 53
3.3.5 CO2培養箱(CO2 incubators) 54
3.3.6冷凍離心機(Refrigerated Centrifuge) 55
3.3.7斜式旋轉濃縮機(Rotary Evaporation) 55
3.3.8振盪混合器(Vortex Mixer) 55
3.3.9光致螢光光譜儀(Photoluminescence,PL) 56
3.3.10熱重分析儀(Thermogravimetric analysis,TGA) 56
3.3.11紫外線光譜儀(UV/VIis spectrophotometer,UV/Vis) 57
3.3.12電灑游離質譜儀(Electrospray Ionization Mass Spectrometer) 58
3.3.13螢光顯微鏡(Fluorescence microscope) 59
3.3.14原子力顯微鏡(Atomic Force Microscpoic,AFM) 59
3.3.15奈米粒徑分析儀(Dynamic Light Scattering,DLS) 60
3.3.16差示掃描量熱儀(Differential scanning calorimetry,DSC) 61
3.3.17高解析度場發射掃描式電子顯微鏡(Scanning Electron Microscope,SEM) 61
3.3.18傅里葉轉換紅外光譜(Fourier transform infrared spectroscopy,FTIR) 62
3.3.19液態核磁共振光譜(Nuclear Magnetic Resonance Spectrometer,NMR) 63
3.3.20基質輔助雷射脫附游離飛行時間式質譜儀(Matrix Assisted Laser Desorption Ionization Time-of-Flight Mass Spectrometry,MALDI-TOF MS) 63
3.3.21電化學分析儀(Cyclic Voltammetry,CV) 64
3.3.22流式細胞儀(Flow Cytometers) 65
3.4實驗合成步驟 66
3.4.1合成單體前驅物Methyl thiophene-3-acetate 66
3.4.2合成單體N-[3-(Dimethylamino)propyl]-2-(2-thienyl)acetamide 68
3.4.3合成高分子poly[N-[3-(Dimethylamino)propyl]-2-(2-thienyl)acetamide] 69
3.5樣品製備 70
3.5.1高分子保存方式以及製備方法 70
3.6細胞生物性製備 71
3.6.1磷酸鹽緩衝生理鹽水(Phosphate buffered saline,PBS) 71
3.6.2胰蛋白酶(Trypsin - EDTA) 71
3.6.3細胞培養基(Dulbecco's Modified Eagle Medium,DMEM) 71
3.6.4細胞解凍培養 72
3.6.5細胞培養條件 72
3.6.6細胞生物毒性測試 73
3.6.7溶血試驗 74
3.6.8螢光顯微鏡製備 75
3.6.9製備1 % Fetal Bovine Serum(FBS)+ Phosphate buffered saline(PBS) 75
3.6.10流式細胞儀(Flow cytometer) 76
第四章 結果與討論 77
4.1 材料鑑定 77
4.1.1 M1單體透過傅里葉轉換紅外光譜(FTIR)材料鑑定 78
4.1.2 M1單體透過核磁共振儀(1H和13C NMR)材料鑑定 80
4.1.3 M1單體透過元素分析儀(EA)材料鑑定 82
4.1.4 M1單體透過質譜儀(LC MASS)材料鑑定 83
4.1.5 P1高分子透過核磁共振儀1H NMR材料鑑定 84
4.1.6 P1高分子透過基質輔助雷射脫附游離飛行時間式質譜儀(MALDI-TOF MS)材料鑑定 85
4.1.7 P1高分子透過熱重分析儀(TGA)材料鑑定 86
4.1.8 P1高分子透過熱差式分析儀(DSC)材料鑑定 88
4.2 材料性質分析 89
4.2.1高分子氣體響應前後之核磁共振儀1H NMR光譜圖 89
4.2.2高分子氣體響應前後之紫外線光譜以及光致螢光光譜 91
4.2.3高分子氣體響應前後之循環伏安計量(Cyclic voltammetry)分析 98
4.2.4高分子氣體響應後之螢光穩定度 103
4.2.5高分子氣體響應前後之動態光閃射儀測試 105
4.2.6高分子氣體響應前後之電子顯微鏡(SEM)、原子力顯微鏡(AFM)微結構之探討 107
4.2.7高分子氣體響應前後之可逆測試 111
4.2.8高分子加熱後之溫度響應測試 114
4.3生物影像分析 119
4.3.1高分子氣體響應前後之細胞毒性測試(Cytotoxicity test) 119
4.3.2高分子氣體響應前後之螢光顯微鏡觀察(Fluorescence microscope) 121
4.3.3高分子氣體響應前後之流式細胞儀測試(Flow cytometer) 131
4.3.4高分子氣體響應前後之溶血試驗(Hemolysis test) 134
4.3.5高分子氣體響應前後之活體內毒性測試(In vivo cytotoxicity test) 137
4.3.6高分子氣體響應前後之活體內生物影像(In vivo Biological image) 139
第五章 結論 142
第六章 未來展望 144
第七章 參考文獻 145
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