Tang Yin-min, Huo Yanping, H. Sheng
2014
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Journal
Chemical Journal of Chinese Universities-chinese
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 fluorescent 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 H-1 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 center dot center dot center dot S hydrogen bonds. The aggregation behaviors of zinc salts and compound 4 in solutions were investigated with a variety of techniques, including H-1 NMR, UV-Vis and fluorescence. The fluorescence lifetime of complex 5 was determined in the solid state and its tau 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'-bisphenyl-(1,1'-biphenyl)-4,4'-diamine(NPB) acts as hole transport material.