臺灣博碩士論文加值系統

本論文已多步驟有機合成搭配實驗室已發表之數種水溶性可回收鈀觸媒催化系統合成多種單體，並以Horner Wadsworth Emmons reaction進行單體聚合或共聚合，得到新型共軛高分子poly(phenylene butadieneylene)、poly(phenylene butadieneylene)，其共軛長度較文獻中常見之poly(phenylene vinylene)更高，並對其進行基本性質及光學性質的鑑定。

To explore applications of the aqueous palladium catalytic system, we prepared several monomers for the synthesis of conjugated polymers, poly(phenylene butadienylene/hexatrienylene)s, which were polymerized via Horner-Wadsworth-Emmons reaction. The conjugated structures of these kind of novel polymers were much longer than poly(phenylene vinylene)s, which were commonly discussed by articles. We characterized the basic and optical properties and compared with poly(phenylene vinylene)s.

中文摘要 i
英文摘要 ii
謝誌 iii
目 錄 iv
表目錄 vii
圖目錄 1
第一章 緒論 3
1.1 前言 3
1.2 Horner–Wadsworth–Emmons反應相關研究 4
1.3 Mizoroki-Heck reaction相關研究 8
1.4 Poly (phenylene vinylene)之介紹 11
1.5 Poly (phenylene vinylene)相關研究 14
1.6 研究動機 20
第二章 實驗部分 21
2.1 實驗儀器 21
2.1.1 氣相層析儀(Gas Chromatography, GC) 21
2.1.2 核磁共振光譜儀 (Nuclear Magnetic Resonance Spectroscopy, NMR) 21
2.1.3 高解析質譜儀(High Resolution Mass) 22
2.1.4 紫外光/可見光光譜儀(UV/vis Spectrophotometers) 22
2.1.5 螢光光譜儀(Fluorescence Spectrophotometers) 22
2.1.6 凝膠滲透層析儀(Gel Permeation Chromatography, GPC) 22
2.1.7 熔點觀測儀(Melting Point Apparatus) 23
2.1.8 溶劑純化 23
2.2 實驗藥品 23
2.3 實驗過程 23
2.4 實驗步驟與光譜數據 24
2.4.1 合成共軛高分子PPB 25
2.4.1.1 合成2,5-dimethoxy-4-iodobenzaldehyde 26
2.4.1.2 合成2,5-dihydroxy-4-iodobenzaldehyde 27
2.4.1.3 合成2,5-bis((2-ethylhexyl)oxy)-4-iodobenzaldehyde 28
2.4.1.4 合成PPB單體 29
2.4.1.5 聚合共軛高分子PPB 30
2.4.2 合成共軛高分子co-PPB 31
2.4.2.1 合成2.5-dimethoxyterephthalaldehyde 32
2.4.2.2 合成2,5-dihydroxyterephthalaldehyde 33
2.4.2.3 合成2,5-bis((2-ethylhexyl)oxy)terephthalaldehyde 34
2.4.2.4 合成1,4-diiodo-2,5-dimethoxybenzene 35
2.4.2.5 合成2,5-diiodobenzene-1,4-diol 36
2.4.2.6 合成1,4-bis((2-ethylhexyl)oxy)-2,5-diiodobenzene 37
2.4.2.7 合成tetraethyl ((2E,2E)-(2,5-bis((2-ethylhexyl)oxy)-1,4-phenylene)bis(prop-2-ene-3,1-diyl))bis(phosphonate) 38
2.4.2.8 聚合共軛高分子co-PPB 39
2.4.3 合成共軛高分子PPH 40
2.4.3.1 合成(E)-ethyl 3-(2,5-bis((2-ethylhexyl)oxy)-4-iodophenyl)acrylate 41
2.4.3.2 合成(E)-3-(2,5-bis((2-ethylhexyl)oxy)-4-iodophenyl)prop-2-en-1-ol 42
2.4.3.3 合成(E)-3-(2,5-bis((2-ethylhexyl)oxy)-4-iodophenyl)acrylaldehyde 43
2.4.3.4 合成diethyl((E)-3-(2,5-bis((2-ethylhexyl)oxy)-4-((E)-3-oxoprop-1-en-1-yl)phenyl)allyl)phosphonate 44
2.4.3.5 聚合共軛高分子PPH 45
2.4.4 合成共軛高分子co-PPH 46
2.4.4.1 合成(2E,2E)-diethyl 3,3-(2,5-bis((2-ethylhexyl)oxy)-1,4-phenylene)diacrylate 47
2.4.4.2 合成(2E,2E)-3,3-(2,5-bis((2-ethylhexyl)oxy)-1,4-phenylene)bis(prop-2-en-1-ol) 48
2.4.4.3 合成(2E,2E)-3,3-(2,5-bis((2-ethylhexyl)oxy)-1,4-phenylene)diacrylaldehyde 49
2.4.4.4 聚合共軛高分子co-PPH 50
第三章 結果與討論 51
3.1 以HWE reaction合成共軛高分子PPB、PPH 51
3.2 共軛高分子PPB、PPH之結果與討論 51
3.2.1 共軛高分子PPB、PPH基本性質討論 53
3.2.2 共軛高分子PPB、PPH光學性質討論 54
第四章 結論 56
參考文獻 57
附錄 61

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