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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。
Starting from carbazole, N-ethyl-3,6-diamino carbazole was prepared via N-substitution, nitration and reduction reactions, and then a novel bis-Schiff base The compound, N-ethyl-3,6-di (2-furfurylimino) carbazole, has a yield of 72.36%. The molecular structure, photophysical properties, electrochemical properties and thermal stability of the title compounds were investigated by elemental analysis, FTIR, UV-Vis, 1H NMR, solution and solid state fluorescence spectroscopy, cyclic voltammetry (CV) and TG-DTA analysis. The results showed that the dilute DMF solution of the compound had broad and strong UV absorption in the wavelength range of 200-400 nm. Under the excitation of 365 nm wavelength, the solution emitted blue fluorescence with λem of 446 nm and blue fluorescence of λem = 467 nm. The solid-state fluorescence red-shifted 21 nm compared to the solution fluorescence. The products Eg = 2.19e V, IP = 4.99e V and EA = 2.80e V were obtained from the cyclic voltammetry, which showed that they had good properties of hole and electron transport materials. TG-DTA test showed that the target product has good thermal stability. The compound has potential applications in organic fluorescence, hole injection transport materials and electron transport materials.