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標題: | 新型具蒽醌之芳香族功能性高分子合成及電化學與記憶體元件性質之研究 Synthesis, Electrochemical and Memory Properties of Novel Functional Aromatic Polymers with Anthraquinone Moiety |
作者: | Jung-Hsiang Chang 張容祥 |
指導教授: | 劉貴生(Guey-Sheng Liou) |
關鍵字: | 三苯胺,??,質子耦合電子轉移,記憶體元件, triphenylamine,anthraquinone,proton-coupled electron transfer,memory property, |
出版年 : | 2014 |
學位: | 碩士 |
摘要: | 本論文分成四個章節。第一章序論包含了高性能高分子,質子耦合電子轉移及高分子記憶體材料之介紹。第二章合成新型聚醯胺之二胺單體1-(bis(4-aminophenyl)amino)anthracene-9,10-dione,利用親核性取代反應製得硝基化合物1-(bis(4-nitrophenyl)amino)anthracene-9,10-dione接著以聯胺與鈀金屬催化還原反應方式而合成得之。蒽醌(anthraquinone)於電化學之還原反應可藉由氫鍵及質子化作用之影響來控制電位轉移及反應機制。以循環伏安儀測試方式之結果顯示,發現藉由酸度係數改變可產生電位平移及電位反轉之效應。第三章是以1-(bis(4-aminophenyl)amino)anthracene-9,10-dione以及同分異構物二胺2-(bis(4-aminophenyl)amino)anthracene-9,10-dione 所合成出一系列聚醯亞胺1AQODPI, 1A6FPI, 1AQDSPI, 2AQDSPI,及聚醯胺1AQCHPA, 1AQTPA, 1AQ6FPA, 2AQTPA, 並探討其記憶體性質。由於在α位置取代較β位置取代之蒽醌具有較高非平面結構以及立體阻礙效應而導致非揮發性write-once-read-many-times (WORM)之特性。由此得知記憶體材料之特性是由於電子受體結構之影響。第四章為結論。所合成的高分子在極性非質子型溶劑有好的溶解性,出色的薄膜成型能力,高的玻璃轉化溫度,好的熱穩定性和機械性質,以及較高的HOMO值。 This study consists of four sections. Chapter 1 is the general introduction including preparation of high performance polymer, proton-coupled electron transfer behavior, and polymer memory devices applications. Chapter 2 describes the synthesis and characterization of the novel electroactive polyamides from the new diamine 1-(bis(4-aminophenyl)amino)anthracene-9,10-dione which was prepared by palladium catalyzed hydrazine reduction of 1-(bis(4-nitrophenyl)amino)anthracene-9,10-dione resulting from aromatic nucleophilic substitution reaction. Electrochemical behavior and mechanism of the reduction of anthraquinone moiety are fundamentally studied by the cyclic voltammogram. We obtained the characteristic potential shift and potential inversion results dependent on the basis of pKa values due to the hydrogen-bonding and protonation reaction. Chapter 3 investigates the memory properties of the functional polyimides 1AQODPI, 1A6FPI, 1AQDSPI, 2AQDSPI, and polyamides 1AQCPA, 1AQTPA, 1AQ6FPA, 2AQTPA, prepared from isomeric diamines of 1-(bis(4-aminophenyl)amino)anthracene-9,10-dione and 2-(bis(4-aminophenyl)amino)anthracene-9,10-dione with various dianhydrides and dicarboxylic acids, respectively. α-Substitution anthraquinone-containing polymers with higher non-planar conformation and steric hindrance than β-substitution ones revealed the significance of the electron-accepting structures on the memory effects, resulting in much longer retention time and write-once-read-many-times (WORM) type non-volatile memory behavior. Chapter 4 is conclusion. All polymers had good solubility in many polar aprotic solvents, and exhibited excellent thin-film-forming ability. In addition to high Tg values, good thermal stability, mechanical properties, and higher HOMO energy levels. |
URI: | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/55651 |
全文授權: | 有償授權 |
顯示於系所單位: | 高分子科學與工程學研究所 |
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