4-heptoxy-4'-fluoroazobenzene | 1286673-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-heptoxy-4'-fluoroazobenzene
• 英文别名: (4-Fluorophenyl)-(4-heptoxyphenyl)diazene；(4-fluorophenyl)-(4-heptoxyphenyl)diazene
• CAS: 1286673-45-7
• 化学式: C₁₉H₂₃FN₂O
• 分子量: 314.403
• InChiKey: FYLYFLGALONTCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二(氰基苯)二氯化钯 、 4-heptoxy-4'-fluoroazobenzene 以 乙醇 为溶剂， 生成 bis(μ-chloro)bis(4-heptoxy-4'-fluoroazobenzenyl)dipalladium 、 bis(μ-chloro)bis(4-heptoxy-4'-fluoroazobenzenyl)dipalladium
  参考文献：
  名称：

  Syntheses, Electronic Structures, and Dichroic Behavior of Dinuclear Cyclopalladated Complexes of Push−Pull Azobenzenes

  摘要：

  Eight new chloride-/acetate-bridged dimeric Pd-II complexes have been synthesized by using 4-heptoxyazobenzenes 4'-substituted with groups of varying electron-withdrawing strength (NO2, CN, F, or CO2Et). The effects of charge density distribution and the bridging ligand on the relative proportions of structural and geometrical isomers produced is explored by using NMR spectroscopy. UV-vis spectroscopy reveals a single low-energy absorption for each proligand but three distinct bands for each of the complexes. The origins of the observed absorptions are inferred from the effects of changing the bridging ligands and corroborated by time-dependent density functional theory (TD-DFT) calculations. Dichroic ratio (DR) measurements in two different liquid-crystal (LC.) hosts show decreased performance upon complexation, although the results are notably wavelength dependent. The lowest energy absorption band, associated with intraligand charge-transfer transitions, displays superior dichroism with respect to the adjacent band at higher energy. The transition dipole moment directions calculated via TD-DFT correlate with the observed DR results, implying a decrease in alignment within the LC hosts for the complexes with respect to their proligands.

  DOI：

  10.1021/om101189f

文献信息

• Syntheses, Electronic Structures, and Dichroic Behavior of Dinuclear Cyclopalladated Complexes of Push−Pull Azobenzenes
  作者：Octavia A. Blackburn、Benjamin J. Coe

  DOI：10.1021/om101189f

  日期：2011.4.25

  Eight new chloride-/acetate-bridged dimeric Pd-II complexes have been synthesized by using 4-heptoxyazobenzenes 4'-substituted with groups of varying electron-withdrawing strength (NO2, CN, F, or CO2Et). The effects of charge density distribution and the bridging ligand on the relative proportions of structural and geometrical isomers produced is explored by using NMR spectroscopy. UV-vis spectroscopy reveals a single low-energy absorption for each proligand but three distinct bands for each of the complexes. The origins of the observed absorptions are inferred from the effects of changing the bridging ligands and corroborated by time-dependent density functional theory (TD-DFT) calculations. Dichroic ratio (DR) measurements in two different liquid-crystal (LC.) hosts show decreased performance upon complexation, although the results are notably wavelength dependent. The lowest energy absorption band, associated with intraligand charge-transfer transitions, displays superior dichroism with respect to the adjacent band at higher energy. The transition dipole moment directions calculated via TD-DFT correlate with the observed DR results, implying a decrease in alignment within the LC hosts for the complexes with respect to their proligands.