5,7-bis(p-cyanophenyl)-8-hydroxyquinoline | 1350460-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5,7-bis(p-cyanophenyl)-8-hydroxyquinoline
• 英文别名: 4-[7-(4-Cyanophenyl)-8-hydroxyquinolin-5-yl]benzonitrile；4-[7-(4-cyanophenyl)-8-hydroxyquinolin-5-yl]benzonitrile
• CAS: 1350460-30-8
• 化学式: C₂₃H₁₃N₃O
• 分子量: 347.376
• InChiKey: YJFABLSYFONSNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,7-二溴-8-羟基喹啉 在 四(三苯基膦)钯 、 1,4-环己二烯 、 palladium 10% on activated carbon 、 sodium carbonate 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 水 、 丙酮 、 甲苯 为溶剂， 反应 39.0h， 生成 5,7-bis(p-cyanophenyl)-8-hydroxyquinoline
  参考文献：
  名称：

  Synthesis, characterization and DFT investigation of aluminum complexes of aryl- substituted-8-hydroxyquinoline

  摘要：

  New aryl substituted 8-hydroxyquinoline derivatives have been synthesized. The compounds were characterized by H-1, C-13-NMR spectroscopy and mass spectrometry. The aluminum complexes of these derivatives show strong green emission in the range 530-535 nm with high quantum yield compared to the parent tris (8-hydroxyquinolinato)aluminum(III) complex. The structure of the aryl-substituted 8-hydroxyquinoline aluminum complexes in the ground state have been optimized It the B3LYP/6-31G* level of theory. The parent 8-hydroxyquinoline has also been examined using this method with the same basis set. A clear correlation between the shortening of the Al-N bond and red shift in the fluorescence emission band was observed. We have also found that substitution at the 5 and 7 position of the 8-hydroxyquinoline ligand cause simultaneous energy lowering of both highest occupied molecular orbital and the lowest unoccupied molecular orbital with the 5, 7-aryl substituted derivatives exhibiting the greatest effect. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.06.033

文献信息

• Synthesis, characterization and DFT investigation of aluminum complexes of aryl- substituted-8-hydroxyquinoline
  作者：FakhrEldin O. Suliman、Saleh N. Al-Busafi、Moza Al-Risi、Khalifa N. Al-Badi

  DOI：10.1016/j.dyepig.2011.06.033

  日期：2012.3

  New aryl substituted 8-hydroxyquinoline derivatives have been synthesized. The compounds were characterized by H-1, C-13-NMR spectroscopy and mass spectrometry. The aluminum complexes of these derivatives show strong green emission in the range 530-535 nm with high quantum yield compared to the parent tris (8-hydroxyquinolinato)aluminum(III) complex. The structure of the aryl-substituted 8-hydroxyquinoline aluminum complexes in the ground state have been optimized It the B3LYP/6-31G* level of theory. The parent 8-hydroxyquinoline has also been examined using this method with the same basis set. A clear correlation between the shortening of the Al-N bond and red shift in the fluorescence emission band was observed. We have also found that substitution at the 5 and 7 position of the 8-hydroxyquinoline ligand cause simultaneous energy lowering of both highest occupied molecular orbital and the lowest unoccupied molecular orbital with the 5, 7-aryl substituted derivatives exhibiting the greatest effect. (C) 2011 Elsevier Ltd. All rights reserved.