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新型含噻吩基8-羟基喹啉锌配合物的合成及光电性能
引用本文:汤胤旻,霍延平,胡升,张焜,赵丰华,欧阳新华.新型含噻吩基8-羟基喹啉锌配合物的合成及光电性能[J].高等学校化学学报,2014,35(1):48-53.
作者姓名:汤胤旻  霍延平  胡升  张焜  赵丰华  欧阳新华
作者单位: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
基金项目: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.
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
收稿时间:2013-05-24

Synthesis and Photoelectricity of Novel Zn Metal Complex Based on 8-Hydroxyquinoline with Thiophene Group
TANG Yinmin,HUO Yanping,HU Sheng,ZHANG Kun,ZHAO Fenghua,OUYANG Xinhua.Synthesis and Photoelectricity of Novel Zn Metal Complex Based on 8-Hydroxyquinoline with Thiophene Group[J].Chemical Research In Chinese Universities,2014,35(1):48-53.
Authors:TANG Yinmin  HUO Yanping  HU Sheng  ZHANG Kun  ZHAO Fenghua  OUYANG Xinhua
Institution: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
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.
Keywords:Thiophene  8-Hydroxyquinoline  Zinc complex  NMR titration  Fluorescence lifetime  Electroluminescent device
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