高等学校化学学报 ›› 2014, Vol. 35 ›› Issue (1): 48.doi: 10.7503/cjcu20130487

• 有机化学 • 上一篇    下一篇

新型含噻吩基8-羟基喹啉锌配合物的合成及光电性能

汤胤旻1, 霍延平1(), 胡升1, 张焜1, 赵丰华1, 欧阳新华2   

  1. 1. 广东工业大学轻工化工学院, 广州 510006
    2. 中国科学院宁波材料技术与工程研究所, 宁波 315201
  • 收稿日期:2013-05-24 出版日期:2014-01-10 发布日期:2013-07-02
  • 作者简介:联系人简介: 霍延平, 男, 博士, 教授, 主要从事金属有机光电材料的研究. E-mail:yphuo@gdut.edu.cn
  • 基金资助:
    国家自然科学基金(批准号: 21172047, 21001030, 51273209)和广州市珠江科技新星项目(批准号: 2012J2200099)资助

Synthesis and Photoelectricity of Novel Zn Metal Complex Based on 8-Hydroxyquinoline with Thiophene Group

TANG Yinmin1, HUO Yanping1,*(), HU Sheng1, ZHANG Kun1, ZHAO Fenghua1, OUYANG Xinhua2   

  1. 1.School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China
    2. Ningbo Institute of Materials Technology & Engineering, Chinese Academy of Sciences, Ningbo 315201, China
  • Received:2013-05-24 Online:2014-01-10 Published:2013-07-02
  • Contact: HUO Yanping E-mail:yphuo@gdut.edu.cn

摘要:

设计合成了含噻吩基的新型配体(E)-2-[2-(3-噻吩基)乙烯基]-8-羟基喹啉(4)及相应的锌配合物5, 产物结构经核磁共振、 红外光谱和元素分析进行表征. 利用X射线单晶衍射仪测定了中间体(E)-2-[2-(3-噻吩基)乙烯基]-8-乙酰氧基喹啉(3)和配体4的单晶结构, 结果表明中间体3晶体分子间并无明显的氢键作用, 分子间呈交错堆叠; 配体4分子之间由硫氢氧键弱作用相互排列形成网状结构. 通过核磁滴定及紫外和荧光滴定模拟了配体4在溶液中与金属锌的配位过程. 固体荧光寿命研究结果表明, 配合物5的荧光寿命为18.8 ms. 通过电致发光器件研究发现, 配合物5作为发光层具有良好的电致发光性能, 同时具有较好的电子传输能力.

关键词: 噻吩, 8-羟基喹啉, 锌配合物, 核磁滴定, 荧光寿命, 电致发光器件

Abstract:

8-Hydroxyquinoline has long been employed as analytical and separating agents due to its universal chelating ability offered by the heterocyclic N and phenolate O atoms and fiuorescent property possessed by the conjugate system. In order to increase its fluorescence capability and conjugate system, 3-thiophene has been added. A novel 8-hydroxyquinoline derivative ligand containing thiophene group (E)-2-[2-(3-thiophenyl)ethenyl]-8-hydroxyquinoline(4) and its corresponding zinc complex(5) were synthesized and identified via 1H NMR, FTIR, UV-Vis, X-ray structural analysis and elemental analyses. The crystal structures of intermediate (E)-2-[2-(3-thiophenyl)ethenyl]-8-acetoxyquinoline(3) and ligand 4 were characterized by single-crystal X-ray diffraction. X-Ray structural analysis showed that there was no obvious hydrogen-bonding interaction between the molecules of compound 3. The crystal reticular structure of compound 4 was constructed as a result of intermolecular O-H…S hydrogen bonds. The aggregation behaviors of zinc salts and compound 4 in solutions were investigated with a variety of techniques, including 1H NMR, UV-Vis and fluorescence.The fluorescence lifetime of complex 5 was determined in the solid state and its τ value is 18.8 ms. Organic light-emitting diodes built using complex 5 emitted yellow light, in which the 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene(TPBi) acts as the electronic transmission layer, while N,N'-bis-(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine(NPB) acts as hole transport material.

Key words: Thiophene, 8-Hydroxyquinoline, Zinc complex, NMR titration, Fluorescence lifetime, Electroluminescent device

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