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研究生:王鼎傑
研究生(外文):Dean-Jay Wang
論文名稱:具有電子授受基團結構之芳香族高分歧聚醯胺合成與性質研究
論文名稱(外文):Synthesis and Properties of Hyperbranched Aromatic Polyamides Containing Donor and Acceptor Groups
指導教授:汪昆立
指導教授(外文):Kun-Li Wang
口試委員:廖德章鄭如忠黃聲東
口試委員(外文):Der-Jang LiawRu-Jong ZhengSheng-Tung Huang
口試日期:2012-06-25
學位類別:碩士
校院名稱:國立臺北科技大學
系所名稱:化學工程研究所
學門:工程學門
學類:化學工程學類
論文種類:學術論文
論文出版年:2012
畢業學年度:100
語文別:中文
論文頁數:86
中文關鍵詞:高分歧化聚醯胺三苯胺134-噁二唑
外文關鍵詞:HyperbranchedPolyamideTriphenylamine134-oxadiazole
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利用一甲基二硝基的三苯胺1,3,4-噁二唑結構,將甲基氧化成羧基,更進一步將二硝基以Pd/C-聯胺還原後,合成具有一新型三苯胺1,3,4-噁二唑結構(6)含有一羧基二胺基AB2的單體進行自我縮聚反應形成具有多數末端胺基之官能基。此高分歧化聚醯胺為含有大量的胺基末端基,其與acetyl chloride、benzoyl chloride、4-nitrobenzoyl chloride、pentanoyl chloride、1-(4-methoxyphenyl)ethanone進行末端基取代反應後,有較好的溶解性如DMSO,DMF,NMP,DMAc。
以FT-IR和NMR鑑定其結構;UV及PL光譜分析其光學性質;以TGA和DSC測定其熱性質。高分歧聚醯胺的NMP溶液在264~284nm和372~382nm有UV-vis吸收峰,而434~560nm有PL放射峰。其熱性質玻璃轉移溫度並無看出,在氮氣下的5%重量損失溫度為344~455℃,黏度為0.09~0.14 dL/g。其電化學性質是由循環伏安法所檢測,高分歧化聚醯胺的HOMO和LUMO值可藉由氧化電位和吸收光譜的起始波長計算而得,分別是-5.34~ -5.2 eV and -2.82~ -2.73 eV。


4-Nitro-N-(4-nitrophenyl)-N-(4-(5-(p-tolyl)-1,3,4-oxadiazol-2-yl)phenyl)aniline were synthesized via the cesium fluoride-mediated N-arylation reactions of 4-(5-(p-tolyl)-1,3,4-oxadiazol-2-yl)aniline with 1-fluoro-4-nitrobenzene, followed by oxidation reaction by potassium permanganate. Further palladium-catalyzed hydrazine reduction led to a new triphenylamine-based AB2 type monomer containing a carboxylic acid and two amino groups. The self-polycondensation of the AB2 monomer (6) afforded hyperbranched poly(triphenylamine-1,3,4-oxadiazole amide)s with amino end groups. The numerous amino end groups of the hyperbranched polyamide were modified by endcapping with acetyl chloride, benzoyl chloride, 4-nitrobenzoyl chloride,pentanoyl chloride and 1-(4-methoxyphenyl)ethanone.

The structures of hyperbranched polymers were confirmed by FT-IR and NMR. The optical properties were analyzed by UV-Vis and PL spectroscopy. The thermal properties were measured by TGA and DSC. The hyperbranched polyamide exhibited UV-Vis absorption band at 264~284 nm and 372~384nm and showed PL maxium emission peaks at 434~560nm in NMP solution. The glass-transition temperatures were not discernible and 5% weight loss temperature was 344~455℃ under nitrogen. The inherent viscosity of the polymer were 0.09~0.14 dL/g. The electrochemical properties of the hyperbranched polyamide were investigated by cyclic voltammetry. The energy levels of the HOMO and the LUMO wewe respectively estimated as -5.34~ -5.2 eV and -2.82~ -2.73 eV from the oxidation potential and the onset absorption wavelength of the UV-vis spectra.


摘要 i
ABSTRACT ii
誌謝 iv
目 錄 v
表目錄 viii
圖目錄 ix
附圖目錄 xi
第一章 緒論 1
1.1 高分歧化聚合物 1
1.1.1 簡介 1
1.1.2 歷史 4
1.1.3 分歧度(Degree of branching) 5
1.2 聚合方法 6
1.2.1單一單體聚合法(Single-monomer methodology,SMM) 6
1.2.2 雙單體聚合法(Double-monomer methodology,DMM) 12
1.4 聚醯胺(Polyamide) 17
1.5 三苯胺(Triphenylamine) 18
1.6 1,3,4-Oxadiazole 20
1.7 含有電子給體和電子受體化合物介紹 21
1.8 分子設計 24
第二章 實驗 25
2.1 藥品 25
2.2 儀器設備 26
第三章 含三苯胺推電子官能基及1,3,4-噁二唑拉電子官能基之芳香族高分歧高分子合成 29
3.1單體合成 32
5-p-Tolyl-2H-tetrazole(1) 之製備 32
2-(4-Nitro-phenyl)-5-p-tolyl-[1,3,4]oxadiazole (2) 之製備 32
4-(5-p-Tolyl-[1,3,4]oxadiazol-2-yl)-phenylamine (3) 之製備 33
4-nitro-N-(4-nitrophenyl)-N-(4-(5-(p-tolyl)-1,3,4-oxadiazol-2-yl)phenyl)aniline (4)之製備 34
4-(5-(4-(bis(4-nitrophenyl)amino)phenyl)-1,3,4-oxadiazol-2-yl)benzoic acid (5)之製備 35
4-(5-(4-(bis(4-aminophenyl)amino)phenyl)-1,3,4-oxadiazol-2-yl)benzoic acid (6)之製備 36
3.2 高分子合成 37
HBP的聚合 37
HBP-1的聚合 37
HBP-2的聚合 37
HBP-3的聚合 38
HBP-4的聚合 38
HBP-5的聚合 38
第四章 結果與討論 39
4.1 單體鑑定 39
4.2 高分子鑑定 40
4.2.1高分歧化聚醯胺 41
4.2.2末端基取代反應(End-Capping reaction) 43
4.3高分歧化聚醯胺性質 45
4.3.1 溶解性質測試 45
4.3.2黏度性質及分子量測試 46
4.3.3熱性質測試 48
4.3.4光學與電化學性質測試 51
第五章 結論 59
參考文獻 60
附圖 69


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