6-cyano-1-phenyl-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-cyano-1-phenyl-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]quinoline
• 英文别名: 1-Phenyl-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]quinoline-6-carbonitrile；1-phenyl-3-(trifluoromethyl)pyrazolo[3,4-b]quinoline-6-carbonitrile
• 化学式: C₁₈H₉F₃N₄
• 分子量: 338.291
• InChiKey: XHSNVERSMABCIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-Phenyl-5-trifluoromethyl-2H-pyrazol-3-ol 在 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 反应 24.5h， 生成 6-cyano-1-phenyl-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]quinoline
  参考文献：
  名称：

  Synthesis, electrochemical, photophysical, and electroluminescent properties of organic dyes containing pyrazolo[3, 4-b]quinoline chromophore

  摘要：

  Organic dyes containing trifluoromethylated-pyrazolo[3, 4-b]quinoline were synthesized by using condensation reaction between substituted pyrazolo-4-formaldehyde and aryl amines in moderate yields. Quantum calculation, electrochemical, photophysical, and electroluminescent properties were discussed in detail. Electron-withdrawing groups at 6-position of dyes stabilized the LUMO energy levels significantly resulting in red-shifted absorption/emission spectra. Addition of electron-donating group destabilized the HOMO strongly and the LUMO energy levels slightly resulting in red-shifted absorption maxima, but in blue-shifted emission maxima. Experimental and quantum calculation results are presented here to explain this unusual phenomenon. A linear relationship of dipole moments versus Stokes shifts is obtained for these fluorophores, where the increase of dipole moment is accompanied by a decrease in Stokes shift. Organic light-emitting diodes based on selected dyes showed emission at 456 nm, maximum external quantum efficiency at 1.43%, and current efficiency at 1.95 cd/A. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.05.002