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Development of Highly Fluorescent Materials Containing Pyrazine Ring

含吡嗪环高荧光材料的研制

基本信息

批准号：
07651068
负责人：
ISOMURA Kazuaki
金额：
$ 1.09万
依托单位：
Kitakyushu National College of Technology
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
1995
资助国家：
日本
起止时间：
1995 至 1996
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-07651068/
关键词：
fluorescence electronic-luminescence pyrazing ring synthesis quinoxalline ピラジン蛍光物質

项目摘要

Recently, fluorescent compounds are expected as the material for flat display, using electro-luminescence device, althogh some other applications have been realized. In the course of our reserch on liquid crystal and Langmuier-Blodgett film using pyrazine derivatives, we noticed that pyrazine derivatives show strong fluorescence. In this investigation, we synsthesize many pyrazine derivatives to develope highly fluorescnet material. Important results are as follow ;1. Three methds fot the synthesis of pyrazine derivatives were investigted. (1) Reaction of lithiated mechylpyrazine with carbonyl compounds followed by dehydration was revealed to give alkenyl pyrazine derivatives. (2) Azidomethylaryl ketones gave 2,5-diarylpyrazine by the reaction with triphenylphosphine. (3) Reactions of glyoxals or bromomethyl ketones with o-phenylenediamine gave quinoxalilne derivatives.2. In the case of 2,5-diarylpyrazines, electron-donating groups, such as p-methoxyphenyl or furyl group, ebhanced the fluorescence. Conjugative effects of large pi-electron system, such as naphthyl group, was also edffective for the enhancement of fluorescence. However, the furyl derivative in solution was not stable as to decompose in a few days.3. In the case of quinoxaline derivatives, substitution by methoxyphenyl, 2,3-dimetoxyphenyl, or N,N-dimethyphenyl group cenhanced fluorescence of the compound. Although, the fluorescence of these compounds were not strong as 2,5-diarylpyrazine, they were shown to be very stable.In this investigation, we could demonstrate that substitution by the group, having electron-donating effect and conjugative effect, enhances the fluorescence. On the basis of these results, we are now planning to prepare more stable pyrazine derivattives showing strong fluorescence.

最近，尽管已经实现了一些其他应用，但荧光化合物有望作为使用电致发光器件的平板显示器的材料。在我们使用吡嗪衍生物对液晶和Langmuier-Blodgett薄膜进行研究的过程中，我们注意到吡嗪衍生物表现出强烈的荧光。在这项研究中，我们合成了许多吡嗪衍生物来开发高荧光材料。重要结果如下： 1．研究了三种吡嗪衍生物的合成方法。 (1)锂化甲基吡嗪与羰基化合物反应，然后脱水，得到烯基吡嗪衍生物。 (2)叠氮基甲基芳基酮与三苯基膦反应得到2,5-二芳基吡嗪。 (3)乙二醛或溴甲基酮与邻苯二胺反应得到喹喔啉衍生物。2．就2,5-二芳基吡嗪而言，给电子基团，例如对甲氧基苯基或呋喃基，增强了荧光。萘基等大π电子体系的共轭效应也对荧光增强有作用。但呋喃基衍生物在溶液中不稳定，几天后就会分解。 3．在喹喔啉衍生物的情况下，被甲氧基苯基、2,3-二甲氧基苯基或N,N-二甲基苯基取代可增强化合物的荧光。虽然这些化合物的荧光不如2,5-二芳基吡嗪强，但它们非常稳定。在本研究中，我们可以证明具有给电子效应和共轭效应的基团的取代增强了荧光。基于这些结果，我们现在计划制备更稳定、具有强荧光的吡嗪衍生物。