Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (04): 576-581. Previous Articles     Next Articles

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三苯基咪唑类化合物的合成及其紫外、荧光性质研究

汪瑞祥,邵强,王婷婷,曾和平   

  1. (华南理工大学化学与化工学院功能分子研究所 广州 510641)
  • 收稿日期:2009-09-09 修回日期:2010-10-23 发布日期:2010-04-28
  • 通讯作者: 曾和平 E-mail:zenghp@scnu.edu.cn
  • 基金资助:

    国家级.国家自然科学基金

Synthesis, Ultraviolet and Fluorescence Properties of Triphenyl Imidazole Compounds

Wang Ruixiang Shao Qiang Wang Tingting Zeng Heping   

  1. (Institute of Functional Molecules, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641)
  • Received:2009-09-09 Revised:2010-10-23 Published:2010-04-28

Four triphenyl imidazole compounds including 4-(4,5-diphenyl-1H-imidazol-2-yl)benzaldehyde (2a), 4-[4,5-bis(3-nitrophenyl)-1H-imidazol-2-yl]benzaldehyde (2b), 4-(1-benzyl-4,5-diphenyl-1H-imidazol- 2-yl)benzaldehyde (2c) and 4-[1-benzyl-4,5-bis(3-nitrophenyl)-1H-imidazol-2-yl]benzaldehyde (2d) have been synthesized. All the compounds have been identified by FT-IR, NMR and MS techniques. Single crystal of 2c suitable for X-ray measurement was obtained from ethyl acetate/petroleum ether solvent, which belongs to a triclinic system with space group and cell parameters of a=0.73796(15) nm, b=0.90136(18) nm, c=1.6644(3) nm, α=86.87(3)°, β=78.25(3)°, γ=89.94(3)°, V=1.0822(4) nm3, Dc=1.272 g/cm3, Z=2, F(000)=436, μ=0,077 mm-1, R1=0.0459, wR2=0.1303. Their ultraviolet and fluorescence properties have been studied. The results show that the nitro and benzyl groups influence the absorption and emission spectra of these compounds. The two groups induce blue-shift in the ultraviolet spectra. But in the fluorescence spectra, the benzyl group generates blue-shift while the nitro group causes red-shift. The fluorescence lifetime of 2a and 2c in different solvents has been measured. These results are the base of studying nonlinear optical properties such as two-photon absorption and two-photon fluorescence.

Key words: triphenyl imidazole, lophine, crystal structure, ultraviolet, fluorescence