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研究生:陳宗禾
研究生(外文):Tsung-Ho Chen
論文名稱(外文):Polyphenylene Linked Multi-functional Phthalimides : Synthesis, Solid-State Structures, and Ring-Opening Metathesis Polymerization
指導教授:周德璋周德璋引用關係
學位類別:碩士
校院名稱:國立中正大學
系所名稱:化學所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2005
畢業學年度:93
語文別:中文
論文頁數:203
中文關鍵詞:鍵入論文中文關鍵字並利用英文逗號來區分
外文關鍵詞:PolyphenylenePhthalimides
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2,3-二氰基二氫醌 (22) 可藉由一連串的氧化、狄爾斯-亞德環化加成反應、烯醇化、二氫醌羥基甲基化、水解氰基為二酸與酸性條件下脫水等反應步驟,合成起始物酸酐 26 。酸酐 26 與共軛體系的氨類化合物,以控制當量數及反應濃度,進行脫水縮合反應後,得到單邊 [1+1] 與雙邊 [2+1] 的醯亞胺化合物。醯亞胺化合物 40 、 41 、 44 於合成過程中,會得到不同構形的異構物,我們以高磁場之氫核磁共振光譜儀,經由升溫實驗,克服結構中立體阻礙所造成的能障,對於此三個化合物之光譜分析,成弗o到合理的解釋。
於 X - 射線單晶結構解析中,除了化合物 40 、41 與 44 之外,我們發現在單一晶格中,都存在有相同比例的鏡像異構物。醯亞胺化合物 42 、 43 、 44 與 46 ,於固態解析下,雙邊的亞甲基橋是互為反式並且雙邊的異吲哚環面又互為共平面,此二個現象推測是因為分子自身是以最低能量且最穩定狀態來進行堆疊。
醯亞胺化合物 37 、 38 、 40 與 45 ,以釕碳烯金屬化合物 作為催化劑,進行開環置換聚合反應。就聚合特性而言,所得四個聚合物其所得聚合物分佈指數 (PDI) 皆小於1.4 ,屬於典型的活性聚合。
The anhydride 26 used as starting material was made from 2,3-dicyanohydroquinone via a series of treatments, such as oxidation, Diels-Alder cycloaddition, enolization, methylation, basic hydrolysis, and acidic dehydration. The condensations of anhydride 26 with conjugated amines were successfully achieved under specific concentration or equivalent conditions to give both [1+1] and [2+1] imide products. The conformational isomers of imide 40, 41, 44 were also detected in our characterizations. In dynamic NMR studies, the interconversions of the conformational isomers of each compound were obviously observed, because the increasing temperature technique overcame the steric hindrance of single bond rotations. The phenomena shown in NMR spectra provided us reasonable evidences for the isomers we found.
Except compounds 40, 41, and 44 , we found that there exists enantiomers in equal ratio inside each unit cell, in the X-ray diffraction characterization for each imide product. In the solid-state structural analysis of each diimide compound, we observed the methylenes on the bridges were trans to one another, and the isoindole planes of either sides of the imide molecules were coplanar with one another. By these the crystalline packing pattern shown, we may estimate that the observed conformations of imides correspond to most steady energetic requirements for crystalline packings.
Imide 37, 38, 40, and 45, were also reacted with ruthenium carbene catalyst to undergo ring-opening metathesis polymerization (ROMP) in our researches. The polymerization feature of the four polymers obtained was also analyzed to give respective PDI value. All of the PDI values are lower than 1.4, these ROMP was classified as typical active polymerization.
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