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Synthesis, electropolymerization, and electrochromic performances of two novel tetrathiafulvalene–thiophene assemblies
e-Polymers ( IF 3.7 ) Pub Date : 2020-07-20 , DOI: 10.1515/epoly-2020-0044
Yuhao Li 1 , Shixiong Deng 1 , Pengfei Cai 1 , Chenyun Wang 1 , Han Wang 2 , Yongjia Shen 1
Affiliation  

Abstract 6,7-Bis(hexylthio)-2-[(2-hydroxyethyl)thio]-3-methylthio-tetrathiafulvalene (TTF-2) is coupled with thiophene-3-carboxylic acid and thiophene-3,4-dicarboxylic acid by Steglich esterification, respectively, to afford 2-((4′,5′-bis(hexylthio)-5-(methylthio)-[2,2′-bi(1,3-dithiolylidene)]-4-yl)thio)ethyl thiophene-3-carboxylate (TTF-Th) and bis(2-((4′,5′-bis(hexylthio)-5-(methylthio)-[2,2′-bi(1,3-dithiolylidene)]-4-yl)thio)ethyl)thiophene-3,4-di-carboxylate (DTTF-Th). Their structures were characterized by ESI-MS, 1H NMR, and elemental analysis. Electropolymerization of TTF-Th and DTTF-Th was conducted with 0.1 M n-Bu4NPF6. The results indicated that both assemblies could rapidly form polymers via electrochemical deposition. In addition, their electrochromic performances illustrated that the color of P(TTF-Th) could switch from orange-yellow to dark blue, while P(DTTF-Th) changed its color from orange in the neutral state to dark blue in the oxidation state. Moreover, the electrochromic performances of P(DTTF-Th) were better than P(TTF-Th) due to the introduction of one extra TTF unit.

中文翻译:

两种新型四硫富瓦烯-噻吩组装体的合成、电聚合和电致变色性能

摘要 6,7-Bis(hexylthio)-2-[(2-hydroxyethyl)thio]-3-methylthio-tetrathiafulvalene (TTF-2) 通过以下方式与噻吩-3-羧酸和噻吩-3,4-二羧酸偶联Steglich 酯化分别得到 2-((4',5'-双(己硫基)-5-(甲硫基)-[2,2'-双(1,3-二硫亚基)]-4-基)硫基)噻吩-3-羧酸乙酯 (TTF-Th) 和 bis(2-((4',5'-bis(hexylthio)-5-(methylthio)-[2,2'-bi(1,3-dithiolylidene)]) -4-yl)thio)ethyl)thiophene-3,4-di-carboxylate (DTTF-Th)。它们的结构通过 ESI-MS、1H NMR 和元素分析表征。TTF-Th 和 DTTF-Th 的电聚合是用 0.1 M n-Bu4NPF6 进行的。结果表明,两种组件都可以通过电化学沉积快速形成聚合物。此外,它们的电致变色性能表明,P(TTF-Th)的颜色可以从橙黄色转变为深蓝色,而P(DTTF-Th)的颜色则从中性态的橙色转变为氧化态的深蓝色。此外,由于引入了一个额外的TTF单元,P(DTTF-Th)的电致变色性能优于P(TTF-Th)。
更新日期:2020-07-20
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