4,5-diphenyl-2(E)-styryl-1-(p-tolyl)-1H-imidazole | 1344744-51-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-diphenyl-2(E)-styryl-1-(p-tolyl)-1H-imidazole
• 英文别名: 1-(4-methylphenyl)-4,5-diphenyl-2-[(E)-2-phenylethenyl]imidazole
• CAS: 1344744-51-9
• 化学式: C₃₀H₂₄N₂
• 分子量: 412.534
• InChiKey: IFWDEGDIVGDRAX-ZBJSNUHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 乙烷,三氯氟- 、 联苯甲酰 在 ammonium acetate 作用下， 以55%的产率得到4,5-diphenyl-2(E)-styryl-1-(p-tolyl)-1H-imidazole
  参考文献：
  名称：

  Kamlet-Taft and Catalan Studies of Some Novel Y-Shaped Imidazole Derivatives

  摘要：

  开发了一些新颖的Y型咪唑衍生物，并通过NMR和质谱技术对其进行了表征。在多种溶剂中研究了这些咪唑衍生物的光物理性质。研究发现，Kamlet-Taft和Catalan的溶剂标尺最适合描述吸收和荧光发射的溶剂化色移。代表溶剂电子释放能力或碱性的调整系数C β或C SB为负值，表明随着溶剂给电子能力的增强，吸收和荧光谱带向低能方向移动。这一效应可以用发色团共振结构的稳定化来解释。观察到的较低的荧光量子产率可能是由于非辐射失活速率常数的增加。这归因于咪唑环C(2)原子连接的肉桂醛环非共平面性在激发态中导致的平面性损失。这种激发态的几何变化导致重要的斯托克斯位移，减少了在高浓度溶液中的再吸收和再发射效应。

  DOI：

  10.1007/s10895-011-1009-x

文献信息

• Physicochemical studies of some novel Y-shaped imidazole derivatives – A sensitive chemisensor
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Kumar Brindha Devi、Natesan Srinivasan

  DOI：10.1016/j.saa.2011.07.090

  日期：2011.11

  Some novel Y-shaped imidazole derivatives were developed for highly sensitive chemisensors for transition metal ions. A prominent fluorescence enhancement was found in the presence of transition metal ions such as Hg2+, Pb2+ and Cu2+ and it is due to the suppression of radiationless transitions from the n-pi* state in the chemisensors. The HOMO-LUMO energies, electric dipole moment (mu) and the first-hyperpolarizability (beta) values of the investigated molecule have been studied theoretically which reveal that the synthesized molecules have microscopic non-linear optical (NLO) behaviour with non-zero values. (C) 2011 Elsevier B.V. All rights reserved.
• Kamlet-Taft and Catalan Studies of Some Novel Y-Shaped Imidazole Derivatives
  作者：J. Jayabharathi、V. Thanikachalam、K. Brindha Devi、M. Venkatesh Perumal

  DOI：10.1007/s10895-011-1009-x

  日期：2012.3

  Some novel Y-shaped imidazole derivatives were developed and characterized by NMR and mass spectral techniques. The photophysical properties of these imidazole derivatives were studied in several solvents. The Kamlet-Taft and Catalan’s solvent scales were found to be the most suitable for describing the solvatochromic shifts of the absorption and fluorescence emission. The adjusted coefficient representing the electron releasing ability or basicity of the solvent, C β or C SB has a negative value, suggesting that the absorption and fluorescence bands shift to lower energies with the increasing electron-donating ability of the solvent. This effect can be interpreted in terms of the stabilization of the resonance structures of the chromophore. The observed lower fluorescence quantum yield may be due to an increase in the non-radiative deactivation rate constant. This is attributed to the loss of planarity in the excited state provided by the non co-planarity of the cinnamaldehyde ring attached to C(2) atom of the imidazole ring. Such a geometrical change in the excited state leads to an important Stokes shift, reducing the reabsorption and reemission effects in the detected emission in highly concentrated solutions.

  开发了一些新颖的Y型咪唑衍生物，并通过NMR和质谱技术对其进行了表征。在多种溶剂中研究了这些咪唑衍生物的光物理性质。研究发现，Kamlet-Taft和Catalan的溶剂标尺最适合描述吸收和荧光发射的溶剂化色移。代表溶剂电子释放能力或碱性的调整系数C β或C SB为负值，表明随着溶剂给电子能力的增强，吸收和荧光谱带向低能方向移动。这一效应可以用发色团共振结构的稳定化来解释。观察到的较低的荧光量子产率可能是由于非辐射失活速率常数的增加。这归因于咪唑环C(2)原子连接的肉桂醛环非共平面性在激发态中导致的平面性损失。这种激发态的几何变化导致重要的斯托克斯位移，减少了在高浓度溶液中的再吸收和再发射效应。