N,N,N′,N′- Tetraphenyl-1,4-phenylenediamine-Fluorene Alternating Conjugated Polymer: Synthesis, Characterization, and Electrochromic Application

被引:58
作者
Chen, Wen-Hsiang [2 ]
Wang, Kun-Li [1 ]
Liaw, Der-Jang [2 ]
Lee, Kueir-Rarn [3 ]
Lai, Juin-Yih [3 ]
机构
[1] Natl Taipei Univ Technol, Dept Chem Engn & Biotechnol, Taipei 10608, Taiwan
[2] Natl Taiwan Univ Sci & Technol, Dept Chem Engn, Taipei 10607, Taiwan
[3] Chung Yuan Christian Univ, R&D Ctr Membrane Technol, Dept Chem Engn, Chungli 32023, Taiwan
关键词
COLORATION EFFICIENCY MEASUREMENTS; PALLADIUM-CATALYZED AMINATION; AMORPHOUS MOLECULAR MATERIALS; ANODIC-OXIDATION PATHWAYS; TUNGSTEN-OXIDE FILMS; MULTICOLORED ELECTROCHROMISM; ELECTROCHEMICAL PROPERTIES; MAIN-CHAIN; THIN-FILMS; DEVICES;
D O I
10.1021/ma902138g
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A novel N,N,N',N'-tetraphenyl-1,4-phenylenediamine (TPPA)-conlaining arornatic dibromide (3), N, N-bis(4- bromophenyl)-N', N'-bis(4-(2.4,4- trimethylpentan-2-yl)phenyl)-1,4-phenylenediamine, was successfully synthesized. The novel conjugated polymer (4) having number-average molecular weight of 2.05 x 10(4) was prepared via Suzuki coupling from the dibromide (3) with 9,9-dioctylfluorene-2,7-diboronic acid bis(1, 3-propanediol) ester. The conjugated polymer (4) exhibited excellent solubility in common organic solvents such as N-methyl-2-pyrrolidinone (NMP), tetrahydrofuran, chloroform, and toluene at room temperature. The conjugated polymer (4) had useful levels of thermal stability associated with their relatively high glass transition temperature (T-g = 144 degrees C), 10% weight-loss temperatures (T-d10) in nitrogen (T-d10 = 445 degrees C),and char yields at 800 degrees C in nitrogen (59.0%). The hole-transporting and electrochronic properties were examined by electrochemical and spectroelectrochemical methods. Cyclic voltammagrams of the conjugated polymer films cast onto indium-tin oxide (ITO)-coaled glass substrates exhibited two reversible oxidation redox couples at E-1,E-2 value of 0.67 and 1.05 V vs Ag/Ag+ in acetonitrile solution, The conjugated polymer film (4) revealed better stability of electrochromic characteristics and more rapid switching time than model polymers N,112 which has no electron-donating bis(4-(2,4,4-trimethylpentan-2-yl) phenyl)amine group and M3 without electron-donating 2,4,4-trimethylpentan-2-yl substituent. The conjugated polymer film (4) also showed high contrast with color change from pale yellowish to green and then to blue at applied potentials ranging from 0.00 to 1.18 V.
引用
收藏
页码:2236 / 2243
页数:8
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