N-(4-bromo-2,6-difluorophenyl)-N'-(octyl)-naphthalic diimide | 583879-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(4-bromo-2,6-difluorophenyl)-N'-(octyl)-naphthalic diimide
• CAS: 583879-94-1
• 化学式: C₂₈H₂₃BrF₂N₂O₄
• 分子量: 569.402
• InChiKey: WXBOCQHJCRXNJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.64
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  74.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(4-bromo-2,6-difluorophenyl)-N'-(octyl)-naphthalic diimide 、 [5-ethynyl-10,20-diphenylporphinato]zinc(II) 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以83%的产率得到[5-[2',5'-difluoro-4'-(N-(N'-octyl)naphthylic diimide)phenylethynyl]-10,20-diphenylporphinato]zinc(II)
  参考文献：
  名称：

  Synthesis, Electronic Structure, and Electron Transfer Dynamics of (Aryl)ethynyl-Bridged Donor−Acceptor Systems

  摘要：

  The ET dynamics of a series of donor-spacer-acceptor (D-Sp-A) systems featuring (porphinato)zinc(II), (aryl)ethynyl bridge, and arene diimide units were investigated by pump-probe transient absorption spectroscopy. Analysis of these data within the context of the Marcus-Levich-Jortner equation suggests that the pi-conjugated (aryl)ethynyl bridge plays an active role in the charge recombination (CR) reactions of these species by augmenting the extent of (porphinato)zinc(II) cation radical electronic delocalization; this increase in cation radical size decreases the reorganization energy associated with the CR reaction and thereby attenuates the extent to which the magnitudes of the CR rate constants are solvent dependent. The symmetries of porphyrin-localized HOMO and HOMO-1, the energy gap between these two orbitals, and D-A distance appear to play key roles in determining whether the (aryl)ethynyl bridge simply mediates electronic superexchange or functions as an integral component of the D and A units.

  DOI：

  10.1021/ja021278p
• 作为产物：
  描述：

  1,4,5,8-萘四甲酸酐 在 calcium oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 N-(4-bromo-2,6-difluorophenyl)-N'-(octyl)-naphthalic diimide
  参考文献：
  名称：

  Synthesis, Electronic Structure, and Electron Transfer Dynamics of (Aryl)ethynyl-Bridged Donor−Acceptor Systems

  摘要：

  The ET dynamics of a series of donor-spacer-acceptor (D-Sp-A) systems featuring (porphinato)zinc(II), (aryl)ethynyl bridge, and arene diimide units were investigated by pump-probe transient absorption spectroscopy. Analysis of these data within the context of the Marcus-Levich-Jortner equation suggests that the pi-conjugated (aryl)ethynyl bridge plays an active role in the charge recombination (CR) reactions of these species by augmenting the extent of (porphinato)zinc(II) cation radical electronic delocalization; this increase in cation radical size decreases the reorganization energy associated with the CR reaction and thereby attenuates the extent to which the magnitudes of the CR rate constants are solvent dependent. The symmetries of porphyrin-localized HOMO and HOMO-1, the energy gap between these two orbitals, and D-A distance appear to play key roles in determining whether the (aryl)ethynyl bridge simply mediates electronic superexchange or functions as an integral component of the D and A units.

  DOI：

  10.1021/ja021278p