新型具四苯基聯苯胺或側鍊蒽醌基團之芳香族高分子合成與紫外光/可見光/近紅外光電致變色特性之研究

Synthesis and UV-Vis-NIR Electrochromism of Novel Aromatic Polymers Based on Tetraphenylbenzidine Unit or Bearing Pendent Anthraquinone Groups

林昆瑩(Kun-Ying Lin)

指導教授 ： 劉貴生

國立臺灣大學/工學院/高分子科學與工程學研究所/碩士(2010年)

https://doi.org/10.6342/NTU.2010.10468

摘要

本論文分成五個章節，第一章總體序論包含了高性能聚醯胺，聚醯亞胺及其應用之介紹。第二章為新型電致變色高分子之合成及其特性之探討，此聚醯胺之單體N,N'-bis(4-aminophenyl)-N,N'-di(4-methoxyphenyl)-4,4'-biphenyldiamine，是由4-methoxy-4’-nitrodiphenylamine與4,4'-diiodo-biphenyl利用銅當作催化劑進行Ullmann反應生成硝基化合物，接著再用聯胺與鈀金屬催化還原而被合成出。第三章包含了以2-(bis(4-aminophenyl)amino)anthracene-9,10-dione及2-(4-(bis(4-aminophenyl)amino)phenoxy)anthracene-9,10-dione為主體所合成出的二個系列新型陰極/陽極電致變色之聚醯胺。第四章節是以N,N'-bis(4-aminophenyl)-N,N'-di(4-methoxyphenyl)-4,4'-biphenyldiamine， 2-(bis(4-aminophenyl)amino)anthracene-9,10-dione 及2-(4-(bis(4-aminophenyl) amino)phenoxy)anthracene-9,10-dione 為主體所合成出的三個系列新型芳香族聚醯亞胺。第五章為結論。這些新型芳香族高分子之合成與基本特性、電化學及電致變色性質已被研究與比較。所有的高分子在極性非質子型溶劑中有好的溶解性，出色的薄膜成形能力，高的玻璃轉換溫度，好的熱穩定性和機械性質，較低的HOMO值。在利用電化學與光譜電化學的方法下，所有的高分子也展現出色可逆的電致變色特性。這些含三苯胺的高分子由於HOMO值和出色的電化學及熱穩定性也許能被廣泛的應用在電致變色和氣體分離薄膜的材料。

關鍵字

聚醯胺 ； 聚醯亞胺 ； 電致變色

並列摘要

This study was divided into five sections. Charpter 1 is the general introduction including high performance polyamide, polyimide, and their applications. Charpter 2 was the synthesized and characterizations of electrochromic polyamides which was prepared by N,N'-bis(4-aminophenyl)-N,N'-di(4-methoxyphenyl)-4,4'-biphenyl -diamine was synthesized by palladium catalyzed hydrazine reduction of N,N'-bis(4-nitrophenyl)-N,N'-di(4-methoxyphenyl)-4,4'-biphenyldiamine resulting from Cu-mediated Ullmann condensation of 4-methoxy-4’-nitrodiphenylamine with 4,4'-diiodo-biphenyl. Chapter 3 was included two series of novel cathodic-anodic electrochromic aromatic polyamides based on 2-(bis(4-aminophenyl)amino)anthracene-9,10-dione, and 2-(4-(bis(4- aminophenyl)amino)phenoxy)anthracene-9,10-dione. Chapter 4 was three series of novel aromatic polyimides derived from N,N'-bis(4-aminophenyl)-N,N'-di(4- methoxyphenyl)-4,4'-biphenyldiamine, 2-(bis(4- aminophenyl)amino)anthracene- 9,10-dione and 2-(4-(bis(4- aminophenyl)amino)phenoxy)anthracene-9,10-dione. Chapter 5 is conclusions. The synthesis, basic characterization, electrochemical and electrochromic properties of these novel aromatic polymers were investigated and compared. 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 lower HOMO energy levels. All the obtained polymers also revealed excellent reversibility of electrochromic characteristics by the electrochemical and spectroelectrochemical methods. Thus, these triphenylamine-containing polymers may be widely applied in electrochromic materials and membrane of gas separation due to their proper HOMO values, excellent electrochemical and thermal stability.

並列關鍵字

polyamide ； polyimide ； electrochromic

參考文獻

CHAPTER1 REFERENCES AND NOTES

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