Development of new multi-color electrochromic system by use of redox-active pi conjugated compounds

利用氧化还原活性π共轭化合物开发新型多色电致变色系统

基本信息

批准号：
63550646
负责人：
SUGIMOTO Toyonari
金额：
$ 1.02万
依托单位：
KYOTO UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1988
资助国家：
日本
起止时间：
1988 至 1989
项目状态：
已结题

项目摘要

Organic compounds with multi-color change are of current interest from development of new types of display systems. This research project has been carried out with aim of developing such multi-color organic electrochromic systems by use of the following redox-active pi conjugated compounds: (1) tetrakis(2,6-di-tert-butyl-4-hydroxyphenyl)- thieno[3,2-b]thiophene (1), (2) 1,3-dithiole-[n]radialenes (n=3, 4, 5, 6) (2), and (3) 1,3-dithiole-[n]dendralenes (n=3, 4) (3). As for 1 a reversible redox system was constructed with the corresponding two- and four-electron oxidized compounds, the mono- quinone (1') and diquinone (1''). Between the three components a large color change was observed: 1 (pale yellow), 1' (blue), and 1'' (brown red). It was very surprising that 1' and 1'' have absorption maxima at fairly long wavelength region, in spite of their not so large pi conjugation. As a result of some investigations, it was suggested that the excited state (biradical structure) might be located at comparatively low energy level and the transition energy from HOMO to LUMO might become very smaller. The indirect evidence to this suggestion was obtained from the detailed esr measurement of 1' and 1'', in which certainly the biradical involvement was recognized. Also, 2 and 3 exhibited electrochromism between their radical cations and dications. In particular, a comparatively large three color change was observed between 3 (yellow), and the radical cation (dark blue) and dication (green).

具有多色变化的有机化合物是开发新型显示系统的目前感兴趣的。 This research project has been carried out with aim of developing such multi-color organic electrochromic systems by use of the following redox-active pi conjugated compounds: (1) tetrakis(2,6-di-tert-butyl-4-hydroxyphenyl)- thieno[3,2-b]thiophene (1), (2) 1,3-dithiole-[n]radialenes (n=3, 4，5，6）（2）和（3）1,3-二二二二核 - [n] dendralenes（n = 3，4）（3）。至于1，使用相应的两电子和四电子化合物，单酮（1'）和二喹酮（1''）构建了可逆的氧化还原系统。在这三个组件之间观察到了很大的颜色变化：1（浅黄色），1'（蓝色）和1''（棕色）。令人惊讶的是，尽管没有那么大的PI共轭，但1'和1'在相当长的波长区域具有最大最大值。通过一些研究的结果，有人提出激发态（Biradical结构）可能位于相对较低的能级，并且从HOMO到Lumo的过渡能量可能会变得更小。该建议的间接证据是从1'和1''的详细ESR测量中获得的，其中当然可以认识到Biradical参与。另外，有2和3在其激进阳离子和diCation之间表现出电色素。特别是，在3（黄色）和自由基阳离子（深蓝色）和dication（绿色）之间观察到了相对较大的三种颜色变化。