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

  • Yang Hua ,
  • Qian Ying
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  • School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Received date: 2012-08-01

  Revised date: 2012-09-12

  Online published: 2012-09-21

Supported by

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

Abstract

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.

Cite this article

Yang Hua , Qian Ying . Synthesis, Flourescence Properties and Storage Effect of a Novel 1,2,4,5-Tetra(aryl)benzene Dendrimer[J]. Chinese Journal of Organic Chemistry, 2013 , 33(01) : 184 -189 . DOI: 10.6023/cjoc201208001

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