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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (01): 71-77. 上一篇    下一篇

研究论文

双枝[1,3,4]-噁二唑衍生物的合成与荧光性质

孟 康 ; 钱 鹰*   

  1. (东南大学化学化工学院 南京 211189)
  • 收稿日期:2008-01-16 修回日期:2008-06-20 发布日期:2009-01-20
  • 通讯作者: 钱 鹰

Synthesis and Fluorescence Properties of Bisbranched 1,3,4-Oxadiazole Derivatives

Meng, Kang; Qian, Ying*   

  1. (School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189)
  • Received:2008-01-16 Revised:2008-06-20 Published:2009-01-20
  • Contact: Qian, Ying

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1542

被引次数

32

通过Wittig反应和Heck反应合成了三个双枝噁二唑衍生物: N-{{{3,5-二-[5-(4-叔丁基苯基)-1,3,4-噁二唑-2]-苯基}-E-乙烯基}-4-苯基}二苯胺(BBOD-2), N,N-双{{{3,5-二-[5-(4-叔丁基苯基)-1,3,4-噁二唑-2]-苯基}-E-乙烯基}-4-苯基}苯胺(BBOD-3), N,N,N-三{4-{2-{3,5-二-[5-(4-叔丁基苯基)-1,3,4-噁二唑-2]-苯基}-E-乙烯基}苯基}胺(BBOD-4). 化合物结构经过红外光谱、核磁共振谱、质谱和熔点确证, 测定了它们在不同溶剂中的紫外光谱和单光子荧光光谱. BBOD-1, BBOD-2, BBOD-3, BBOD-4在二氯甲烷中的最大吸收峰分别位于295, 390, 398和408 nm; 最大发射峰分别为360, 486, 483和487 nm. 讨论了Stokes位移与溶剂极性的关系.

关键词: 1,3,4-噁二唑衍生物, Wittig反应, Heck反应, 荧光性质

Three novel bisbranched oxadiazole derivatives, N-{4-{2-{3,5-di[5-(4-tert-butylphenyl)-1,3,4- oxadiazol-2-yl]phenyl}-E-vinyl}phenyl}-diphenylamine (BBOD-2), N,N-di{4-{2-{3,5-di[5-(4-tert-buty- phenyl)-1,3,4-oxadiazol-2-yl]phenyl}-E-vinyl}phenyl}aniline (BBOD-3) and N,N,N-tris{4-{2-{3,5-di[5-(4- tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-E-vinyl}phenyl}amine (BBOD-4), were synthesized through Wittig and Heck reactions. Their structures were characterized by IR, 1HNMR, MS and melting points. A detailed spectrum study of these molecules, including absorption and fluorescence in different solvents, was conducted. The maximum absorption peaks in dichloromethane were at 390 nm for BBOD-2, 398 nm for BBOD-3 and 408 nm for BBOD-4, respectively. The maximum emission wavelengths were at 486 nm for BBOD-2, 483 nm for BBOD-3 and 487 nm for BBOD-4 in dichloromethane, respectively. The relationship of Stokes shift with solvent polarity was discussed.

Key words: Wittig reaction, 1,3,4-oxadiazole derivative, Heck reaction, fluorescence property