2-糠醛缩N-乙基-3,6-二氨基咔唑双席夫碱的合成及其性能

发布时间：2018-09-13 11:41

【摘要】：以咔唑为起始原料经N-取代、硝化和还原反应制备中间体N-乙基-3,6-二氨基咔唑,然后以其与2-糠醛发生缩合反应制得新型双席夫碱化合物N-乙基-3,6-二(2-亚糠基亚氨基)咔唑,产率为72.36%。通过元素分析、FTIR、UV-Vis、1H NMR、溶液及固体荧光光谱、循环伏安(CV)和TG-DTA分析研究了标题化合物的分子结构、光物理特性、电化学特性和热稳定性。结果表明,化合物的DMF稀溶液在200~400 nm波段有较宽较强的紫外吸收;在365nm波长激发下,溶液发射深蓝色荧光,λem为446nm,固体荧光为λem=467nm的蓝色荧光,与溶液荧光相比固体荧光红移了21nm。由循环伏安测试得到产物的Eg=2.19e V,IP=4.99e V以及EA=2.80e V,说明其具有良好的空穴和电子传输材料性能。TG-DTA测试显示目标产物具有良好的热稳定性。该化合物在有机荧光、空穴注入传输材料以及电子传输材料方面具有潜在应用前景。
[Abstract]:The intermediate N-ethyl-3-di-6-diamino carbazole was synthesized by nitration and reduction from carbazole as starting material, and then it was condensed with 2-furfural to produce a new bis-Schiff base compound N-ethyl-3- (2-furfuryl imino) carbazole, a new type of bis-Schiff base compound, N- ethyl-3- (2-subfurfuryl imino) carbazole was synthesized by nitration and reduction reaction. The yield was 72.36%. The molecular structure, photophysical properties, electrochemical properties and thermal stability of the title compound were studied by elemental analysis of FTIR IR ~ (-1) H NMR, solution and solid fluorescence spectra, cyclic voltammetry (CV) and TG-DTA. The results show that the DMF dilute solution of the compound has a wide and strong ultraviolet absorption in the 200,400 nm band, and under the excitation of the 365nm wavelength, the solution emits dark blue fluorescence, 位 em is 446 nm, and the solid fluorescence is 位 em=467nm blue fluorescence, and the red shift of the solid fluorescence is 21 nm compared with the solution fluorescence. The results of cyclic voltammetry showed that the target product had good thermal stability and good hole and electron transport properties. The results of cyclic voltammetry showed that the product had good thermal stability and good hole and electron transport properties. The compound has potential applications in organic fluorescence, hole injection transport materials and electron transport materials.
【作者单位】：苏州科技大学化学生物与材料工程学院;江苏省环境功能材料重点实验室;
【基金】：国家自然科学基金项目(51478283) 江苏省高校自然科学基金项目(14KJB150024)资助
【分类号】：O641.4

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