[4-(2,5-diphenyl-3,4-dihydro-2H-pyrazol-3-yl)-phenyl]-diethyl-amine | 88439-40-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [4-(2,5-diphenyl-3,4-dihydro-2H-pyrazol-3-yl)-phenyl]-diethyl-amine
• 英文别名: 4-(1,3-Diphenyl-4,5-dihydro-1H-pyrazol-5-yl)-N,N-diethylaniline；4-(2,5-diphenyl-3,4-dihydropyrazol-3-yl)-N,N-diethylaniline
• CAS: 88439-40-1
• 化学式: C₂₅H₂₇N₃
• 分子量: 369.509
• InChiKey: QELUGBQUMZJURG-UHFFFAOYSA-N

物化性质

• 沸点：
  527.3±60.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  18.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-二乙基-4-氨基苯甲醛 在 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 [4-(2,5-diphenyl-3,4-dihydro-2H-pyrazol-3-yl)-phenyl]-diethyl-amine
  参考文献：
  名称：

  Tuning the Photoinduced Electron-Transfer Thermodynamics in 1,3,5-Triaryl-2-pyrazoline Fluorophores:  X-ray Structures, Photophysical Characterization, Computational Analysis, and in Vivo Evaluation

  摘要：

  series of donor-substituted 1,3,5-triaryl-2-pyrazoline fluorophores were structurally characterized by X-ray analysis, and their photophysical properties studied by steady-state absorption and emission spectroscopy. The photoinduced electron-transfer thermodynamics of the derivatives was estimated on the basis of the spectroscopic data and redox potentials of the fluorophores. The aryl substituents in the 1- and 3-position of the pyrazoline ring influence the photophysical properties of the fluorophores in distinctly different ways. The excited-state equilibrium energy DeltaE(00) is primarily influenced by changes of the substituent in the 1-position, whereas the reduction potential of the fluorophore is essentially determined by the 3-aryl group. Density functional calculations were used to probe the electronic structure and energy ordering of the emissive and the electron-transfer state. The results from the computational analysis agree qualitatively well with the experimental data. In addition, we have evaluated a water soluble pyrazoline derivative in vivo as a potential intracellular pH probe. Membrane permeability, low toxicity, and high quantum yield render the fluorophore attractive for biological applications.

  DOI：

  10.1021/ja028266o

文献信息

• Tuning the Photoinduced Electron-Transfer Thermodynamics in 1,3,5-Triaryl-2-pyrazoline Fluorophores:  X-ray Structures, Photophysical Characterization, Computational Analysis, and in Vivo Evaluation
  作者：Christoph J. Fahrni、Liuchun Yang、Donald G. VanDerveer

  DOI：10.1021/ja028266o

  日期：2003.4.1

  series of donor-substituted 1,3,5-triaryl-2-pyrazoline fluorophores were structurally characterized by X-ray analysis, and their photophysical properties studied by steady-state absorption and emission spectroscopy. The photoinduced electron-transfer thermodynamics of the derivatives was estimated on the basis of the spectroscopic data and redox potentials of the fluorophores. The aryl substituents in the 1- and 3-position of the pyrazoline ring influence the photophysical properties of the fluorophores in distinctly different ways. The excited-state equilibrium energy DeltaE(00) is primarily influenced by changes of the substituent in the 1-position, whereas the reduction potential of the fluorophore is essentially determined by the 3-aryl group. Density functional calculations were used to probe the electronic structure and energy ordering of the emissive and the electron-transfer state. The results from the computational analysis agree qualitatively well with the experimental data. In addition, we have evaluated a water soluble pyrazoline derivative in vivo as a potential intracellular pH probe. Membrane permeability, low toxicity, and high quantum yield render the fluorophore attractive for biological applications.