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有机化学
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有机化学 ›› 2013, Vol. 33 ›› Issue (01): 184-189.DOI: 10.6023/cjoc201208001 上一篇    下一篇

研究简报

树枝形分子1,2,4,5-四芳基苯的合成、荧光性质和电存储效应

杨铧, 钱鹰   

  1. 东南大学化学化工学院 南京 211189
  • 收稿日期:2012-08-01 修回日期:2012-09-12 发布日期:2012-09-21
  • 通讯作者: 钱鹰 E-mail:yingqian@seu.edu.cn
  • 基金资助:

    国家自然科学基金(No. 61178057)资助项目.

Synthesis, Flourescence Properties and Storage Effect of a Novel 1,2,4,5-Tetra(aryl)benzene Dendrimer

Yang Hua, Qian Ying   

  1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189
  • Received:2012-08-01 Revised:2012-09-12 Published:2012-09-21
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 61178057).

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被引次数

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采用钯催化条件下多位点Heck偶联反应, 以芳香八碘代物1,2,4,5-四{4-[N,N-二(4-碘苯基)氨基]苯乙烯基}苯(TPAB-I)和4-(N,N-二苯基)氨基苯乙烯为反应物, 合成了一种新型荧光树枝分子1,2,4,5-四{4-{N,N-二{4-[4-(N,N-二苯基氨基)苯乙烯基]苯基}氨基}苯乙烯基}苯(TPAB-TPA). 目标化合物的结构经过红外光谱、核磁共振谱、高分辨质谱确认. 树枝分子TPAB-TPA在甲苯、乙酸乙酯、四氢呋喃、二氯甲烷和N,N-二甲基甲酰胺(DMF)溶液中的最大荧光发射峰分别位于483, 457, 497, 531, 505 nm. 量子产率分别为0.48, 0.28, 0.23, 0.49, 0.18, 在二氯甲烷和四氢呋喃(THF)中的荧光寿命分别为1.48和1.53 ns. 用循环伏安法测定TPAB-TPA的HOMO能级和LUMO能级分别为-5.16和-2.64 eV. 制备了ITO/TPAB-TPA/Al三明治型电存储器件, ON/OFF电流比大于104, 在1 V的读取电压下, 持续时间达到1000 s.

关键词: 树枝分子, Heck反应, 电存储效应, 荧光性质, 双稳态

Through palladium-catalyzed Heck reaction, a novel fluorescent dentrimer 1,2,4,5-tetra{4-{N, N-di{4-[4-(N, N- diphenylamino)styryl]phenyl}amino}styryl}benzene (TPAB-TPA) was synthesized by aromatic octoiodine-substituted 1,2,4,5-tetra{4-[N, N-bis(4-iodophenyl)amino]styryl}benzene (TPAB-I) and N, N-diphenyl-4-vinylaniline. Its structure was characterized through IR, 1H NMR, HRMS. A detailed spectroscopic study of the dendrimer TPAB-TPA, including absorption, fluorescence emission, fluorescence lifetime and fluorescence quantum yield, was conducted. The maxima emission wavelengths of TPBA-TPA in toluene, ethyl acetate, THF, dichloromethane and DMF were at 483, 457, 497, 531 and 505 nm, respectively. The absorption peaks of the dendrimer were at 400 nm in dichloromethane solution and at 405 nm in DMF solution. The quantum yield was 0.48 (in toluene), 0.28 (in ethyl acetate) and 0.49 (in dichloromethane). The dendrimer possess high solubility in organic solvents and large Stoke’s shift (3434～6168). The fluorescence lifetime was 1.53 ns in THF and 1.48 ns in dichloromethane. The electrochemical properties of the dendrimer TPAB-TPA were explored by cyclic voltammetry. Its HOMO energy level was -5.16 eV and LUMO energy level was -2.64 eV. An organic electrical memory device with the sandwich structure of indium-tin oxide (ITO)/TPAB-TPA/Al was fabricated. The device exhibits a flash memory effect with a high ON/OFF current ratio nearly 104 and a long retention time above 103 s with a read voltage 1.0 V.

Key words: dentrimer, Heck reaction, electrical storage, fluorescent properties, electrical bistability