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.DOCVIP

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 钱永杨珀王建军胡俊伟董冲 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 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、FTTR、UV-Vis、 111 NMR、溶液及固体荧光光谱、循环伏安（CV）和TG-DTA分析研究丫标题化合 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20（/00 nm波段有较宽较强的紫外吸收;在365?波长激发下，溶液发 射深蓝色荧光，Xem为446mn，固体荧光为入em=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, TP=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。 关键词： N-乙基-3; 6-二氨基咔唑;双席夫碱;发光材料; 基金：国家自然科学基金项B Synthesis and Properties of A Novel Bis-Schiff Base Derived from 2-Furaldehyde and N—ethyl-3, 6一diaminocarbazole Qian Yong Yang Po Wang Jianjun Hu Junwei Dong Chong School of Chemistry， Biology and Material Engineering， Suzhou University of Science and Technology; Abstract： With carbazole as raw material, the intermediate N-ethyl-3, 6-diaminocarbazo1e was synthesized through N-alkyl substitution, nitration and reduction reaction successively. Then a novel bis-Schiff base N-ethyl-3，6-bis ( 2-fural ideneimino) carbazole was synthesized from 2-furaldehyde and N-ethyl-3, 6-diaminocarbazole with a yield of72. 36%. Its structure was characterized by elemental analysis, FTIR， UV-Vis, 1 H NMR and E1S-MS. Solution fluorescence, solid fluorescence spectroscopy, cyclic voltammetry ( CV) and TG-DTA thermal analysis were used to study its optical properties, electrochemical properties and thermal stability. The results showed that the target compound has a strong and wide UV absorption band from 200 nm to 400 nm in the dilute solution of DMF，ancl a deep blue fluorescence emission peak at 446 nm excited by 365 nm. Solid fluorescence spectroscopy indicated that the Schiff base has an emission peak at 467 nm, with a 21 nm red shift compared to the solution fluorescence. The optical band gap ( Eg)，ionization potential ( Ip) and electron affinity ( EA) of the target compound are 2. 19, 4. 99 and 2. 80 e V， respectively, c