邻苯胺基取代的1,1,4,4-四氰基丁二烯的合成、表征与性质研究

The Synthesis,Characterization and Properties of Ortho-substituted Aniline 1,1,4,4-tetracyanoquinodimethane Butadiene

以2,5-二溴-4-己基苯胺为起始原料,经与三异丙基硅炔进行Pd/Cu催化Sonogashira偶联反应得到二炔基取代的苯胺.用TBAF可选择性去保护得到单、双脱的端炔化合物.这些化合物能与四氰基乙烯经[2+2]加成开环得到同时带推吸电子的产物5和6.通过1 H NMR、13 C NMR、红外光谱等表征了化合物的结构.由紫外吸收光谱分析发现化合物5和6存在明显的溶剂效应.电化学测量发现所得的目标化合物适合作为新型发光二极管(OLED)材料.

Taking 2 ,5‐dibromo‐4‐hexylbenzenamine as the starting material ,diynyl substituted aniline is obtained by using Pd/Cu catalyzed Sonogashira coupling reaction with triisopropylsilicon alkyne . The resulted compounds can be selectively deprotected by TBAF ,which are subjected to the [2 ＋ 2] cycloaddition reaction with tetracyanoethylene to provide compounds 5 and 6 .The structures of the compounds are characterized by 1 H NMR ,13C NMR and FTIR .The analysis of ultraviolet absorption spectrum finds that the compounds 5 and 6 have significant solvent effect . The electrochemical tests indicate that the target compounds are suitable to be used as novel OLED materials .