9-(4-(N-(4-bromophenyl)-N-(4-chlorophenyl)amino)phenyl)acridine | 863678-24-4

• 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: 9-(4-(N-(4-bromophenyl)-N-(4-chlorophenyl)amino)phenyl)acridine
• 英文别名: 4-acridin-9-yl-N-(4-bromophenyl)-N-(4-chlorophenyl)aniline
• CAS: 863678-24-4
• 化学式: C₃₁H₂₀BrClN₂
• 分子量: 535.87
• InChiKey: LOLXDQZZYLSFSP-UHFFFAOYSA-N

物化性质

• 熔点：
  260-264 °C
• 沸点：
  665.9±55.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.94
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  16.13
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-(4-(N-(4-bromophenyl)-N-(4-chlorophenyl)amino)phenyl)acridine 、 4-ethynyl-N,N-bis(4-methoxyphenyl)aniline 在 N,N-二异丙基乙胺 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三叔丁基膦 作用下， 以 1,4-二氧六环 、 正己烷 为溶剂， 以34%的产率得到9-(4-(N-(4-chlorophenyl)-N-(4-(4-(N',N'-di(4-methoxyphenyl)amino)phenyl)ethynylphenyl)amino)phenyl)acridine
  参考文献：
  名称：

  Photoinduced Charge Transfer Processes along Triarylamine Redox Cascades

  摘要：

  In this paper, we describe the synthesis and photophysical properties of a series of acridinetriarylamine redox cascades. These cascades were designed in order to promote photoinduced hole transfer from an acridine fluorophore into an adjacent triarylamine. The excited dipolar state then injects a hole into the triarylamine redox cascade. Subsequently, the hole migrates along the redox gradient which was tuned by the substituents attached to the triarylamine redox centers. The rate of hole migration was determined by fluorescence lifetime measurements and is in the ns regime and depends strongly on the solvent polarity. The photophysical processes were also investigated by femtosecond broadband pump-probe spectroscopy. Our studies reveal different dynamic processes in the cascades depending on the solvent polarity, e.g., direct charge separation after photoexcitation vs a two step hole transfer mechanism.

  DOI：

  10.1021/ja0511570
• 作为产物：
  描述：

  二苯胺 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三叔丁基膦 、 zinc dibromide 、 sodium t-butanolate 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 192.0h， 生成 9-(4-(N-(4-bromophenyl)-N-(4-chlorophenyl)amino)phenyl)acridine
  参考文献：
  名称：

  Photoinduced Charge Transfer Processes along Triarylamine Redox Cascades

  摘要：

  In this paper, we describe the synthesis and photophysical properties of a series of acridinetriarylamine redox cascades. These cascades were designed in order to promote photoinduced hole transfer from an acridine fluorophore into an adjacent triarylamine. The excited dipolar state then injects a hole into the triarylamine redox cascade. Subsequently, the hole migrates along the redox gradient which was tuned by the substituents attached to the triarylamine redox centers. The rate of hole migration was determined by fluorescence lifetime measurements and is in the ns regime and depends strongly on the solvent polarity. The photophysical processes were also investigated by femtosecond broadband pump-probe spectroscopy. Our studies reveal different dynamic processes in the cascades depending on the solvent polarity, e.g., direct charge separation after photoexcitation vs a two step hole transfer mechanism.

  DOI：

  10.1021/ja0511570