9-1, 1'-联苯-3-基-3-(9, 9'-螺二9H-芴-3-基)-9H-咔唑的合成与性能研究

Synthesis and Properties of 9-1, 1'-Biphenyl-3-yl-3-(9, 9'-Spirobi9H-Fluoren-3-yl)-9H-Carbazole

  • 摘要: 以咔唑为起始原料,经Ullmann反应、溴化反应、Miyaura反应和Suzuki反应合成了9-1, 1’-联苯-3-基-3-(9, 9’-螺二9H-芴-3-基)-9H-咔唑,重点研究了不同的溶剂、碱和催化剂对Suzuki反应中目标产物产率的影响。条件优化实验结果表明:在二氯二叔丁基-(4-二甲基氨基苯基)磷钯(Ⅱ)催化作用下,以乙二醇二甲醚为溶剂并且磷酸钾为碱时,产率达97.1%。通过1H NMR、13C NMR、IR和HRMS表征了化合物的结构,使用TG-DSC、UV-vis研究了化合物的性能。结果显示:该化合物失重5%的温度为472.2 ℃,玻璃化温度为240.1 ℃,吸收焓为71.1 J/g,表现出较好的热稳定性和较高的玻璃化温度。

     

    Abstract: 9-1, 1'-biphenyl-3-yl-3-(9, 9'-spirobi9H-fluoren-3-yl)-9H-carbazole is synthesized using the carbazole as raw material via the Ullmann, Bromination, Miyaura, and Suzuki reactions. The effects of different solvents, bases, and catalysts on the yields of the target product in the Suzuki reaction are extensively explored. The result of condition optimization experiment shows that when ethylene glycol dimethyl ether is used as the solvent, potassium phosphate as the base, dichlorodi-tert-butyl-(4-dimethylaminophenyl) phosphorus palladium(Ⅱ) as the catalyst, a yield of 97.1% is achieved. The structure of the target compound is characterized by 1H NMR, 13C NMR, IR, and HRMS, and the thermal properties are studied by TG-DSC and UV-vis, respectively. The results show that the temperature of 5% mass loss of the target compound is 472.2 ℃, the glass transition temperature is 240.1 ℃, and the absorption enthalpy is 71.1 J/g, respectively, revealing a good thermal stability and high glass transition temperature.

     

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