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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (02): 297-301. 上一篇    下一篇

研究简报

新型1,3,4-噁二唑衍生物的合成与性质研究

张小兵*; 张子敏; 张玉贵 ; 李 敏   

  1. (a河南理工大学瓦斯地质研究所 焦作 454003)
    (b吉林大学材料科学与工程学院 长春 130012)
  • 收稿日期:2008-08-27 修回日期:2008-09-25 发布日期:2009-02-20
  • 通讯作者: 张小兵

Synthesis and Properties of Novel 1,3,4-Oxadiazole Derivatives

Zhang, Xiaobing* ; Zhang, Zimin; Zhang, Yugui ; Li, Min   

  1. (a Institute of Gas-geology, Henan Polytechnic University, Jiaozuo 454003)
    (b Department of Materials Science and Engineering, Jilin University, Changchun 130012)
  • Received:2008-08-27 Revised:2008-09-25 Published:2009-02-20
  • Contact: Zhang, Xiaobing

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被引次数

31 | 4

研制高效载流子传输材料是提高有机电致发光器件性能的关键. 采用对酯对二酰氯(5)与含不同链长烷氧取代基的苯甲酰肼(2)缩合制备了一系列腰接羧基1,3,4-噁二唑衍生物, 即1,4-二[5-(4-烷氧基苯)-1,3,4-噁二唑基]-2,5-二羧基苯(7; 烷氧基＝OCnH2n＋1; n＝8, 12, 16), 并采用UV-vis吸收和荧光光谱对合成物进行了表征. 结果表明: 7的分子结构中羧基的横向引入, 对化合物的光物理性质和能带结构产生较大影响. 这些噁二唑化合物的LUMO及HOMO值分别介于－3.62与－3.58 eV之间及－6.94与－6.90 eV之间, 说明它们可能具有良好的电子传输性.

关键词: 噁二唑衍生物, 电化学, 能带结构

Preparation of high-efficiency carrier transport material is a key to fabricate more efficient and high performance organic and polymeric light-emitting devices. A series of rod-coil 1,3,4-oxadiazole derivatives with lateral carboxyls, 1,4-bis[5-(4-alkoxyphenyl)-1,3,4-oxadiazol-2-yl]-2,5-di(carboxy)benzenes (7; alkoxy＝OCnH2n＋1; n＝8, 12 and 16) were synthesized by condensation of terephthaloyl chloride (5) with benzohydrazides containing alkoxy chains with different lengths (2). The results show that introduction of two carboxyls whose electron-accepting ability is stronger reduces the electron density of the conjugated segment of 7, and thus leads to the absorption maximum bathochromic-shift compared to 8 (without car-boxyl group). Calculation on the representative compound by the Dmol3 package of MS Modeling 3.0 re-vealed that the decrease of energy levels in 7 was due to the change of the frontier molecular orbital distribu-tion in the central benzene ring because of introduction of two carboxyls. The HOMO and LUMO energy levels of the compounds studied are in the range of －3.62～－3.58 eV and －6.94～－6.90 eV, which showed that they functioned well as electron-transporting materials.

Key words: electrochemical, oxadiazole derivative, band structure