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新型1,3,4-噁二唑衍生物的合成与性质研究
引用本文:张小兵,张子敏,张玉贵,李敏.新型1,3,4-噁二唑衍生物的合成与性质研究[J].有机化学,2009,29(2):297-301.
作者姓名:张小兵  张子敏  张玉贵  李敏
作者单位:1. 河南理工大学瓦斯地质研究所,焦作,454003
2. 吉林大学材料科学与工程学院,长春,130012
基金项目:国家自然科学基金,河南理工大学博士科研启动基金 
摘    要: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
收稿时间:2008-8-27
修稿时间:2008-9-25

Synthesis and Properties of Novel 1,3,4-Oxadiazole Derivatives
Zhang Xiaobing,Zhang Zimin,Zhang Yugui,Li Min.Synthesis and Properties of Novel 1,3,4-Oxadiazole Derivatives[J].Chinese Journal of Organic Chemistry,2009,29(2):297-301.
Authors:Zhang Xiaobing  Zhang Zimin  Zhang Yugui  Li Min
Institution:(a Institute of Gas-geology, Henan Polytechnic University, Jiaozuo 454003)
(b Department of Materials Science and Engineering, Jilin University, Changchun 130012)
Abstract: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-bis5-(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.
Keywords:oxadiazole derivative  electrochemical  band structure
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