N,N'-((((5-(bromomethyl)-1,3-phenylene)bis(oxy))bis(methylene))bis(3,1-phenylene))bis(N-phenylpyren-1-amine) | 840531-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: N,N'-((((5-(bromomethyl)-1,3-phenylene)bis(oxy))bis(methylene))bis(3,1-phenylene))bis(N-phenylpyren-1-amine)
• CAS: 840531-11-5
• 化学式: C₆₅H₄₅BrN₂O₂
• 分子量: 965.988
• InChiKey: ZLAUGYRAYOEOPA-UHFFFAOYSA-N

物化性质

• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  18.47
• 重原子数：
  70.0
• 可旋转键数：
  13.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  24.94
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,5-二羟基苯甲醇 、 N,N'-((((5-(bromomethyl)-1,3-phenylene)bis(oxy))bis(methylene))bis(3,1-phenylene))bis(N-phenylpyren-1-amine) 在 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以68%的产率得到
  参考文献：
  名称：

  Energy and Electron Transfer in Bifunctional Non-Conjugated Dendrimers

  摘要：

  \Nonconjugated dendrimers, which are capable of funneling energy from the periphery to the core followed by a charge-transfer process from the core to the periphery, have been synthesized. The energy and electron donors involve a diarylaminopyrene unit and are incorporated at the periphery of these dendrimers. The energy and electron acceptor is at the core of the dendrimer, which involves a chromophore based on a benzthiadiazole moiety. The backbone of the dendrimers is benzyl ether based. A direct electron-transfer quenching of the excited state of the periphery or a sequential energy transfer-electron-transfer pathway are the two limiting mechanisms of the observed photophysical properties. We find that the latter mechanism is prevalent in these dendrimers. The energy transfer occurs on a picosecond time scale, while the charge-transfer process occurs on a nanosecond time scale. The lifetime of the charge separated species was found to be in the range of microseconds. Energy transfer efficiencies ranging from 80% to 90% were determined using both steady-state and time-resolved measurements, while charge-transfer efficiencies ranging from 70% to 80% were deduced from fluorescence quenching of the core chromophore. The dependence of the energy and charge-transfer processes on dendrimer generation is analyzed in terms of the backfolding of the flexible benzyl ether backbone, which leads to a weaker dependence of the energy and charge-transfer efficiencies on dendrimer size than would be expected for a rigid system.

  DOI：

  10.1021/ja044778m
• 作为产物：
  描述：

  N-(3-(1,3-dioxolan-yl)phenyl)-N-phenylpyren-1-amine 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 18-冠醚-6 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.08h， 生成 N,N'-((((5-(bromomethyl)-1,3-phenylene)bis(oxy))bis(methylene))bis(3,1-phenylene))bis(N-phenylpyren-1-amine)
  参考文献：
  名称：

  Energy and Electron Transfer in Bifunctional Non-Conjugated Dendrimers

  摘要：

  \Nonconjugated dendrimers, which are capable of funneling energy from the periphery to the core followed by a charge-transfer process from the core to the periphery, have been synthesized. The energy and electron donors involve a diarylaminopyrene unit and are incorporated at the periphery of these dendrimers. The energy and electron acceptor is at the core of the dendrimer, which involves a chromophore based on a benzthiadiazole moiety. The backbone of the dendrimers is benzyl ether based. A direct electron-transfer quenching of the excited state of the periphery or a sequential energy transfer-electron-transfer pathway are the two limiting mechanisms of the observed photophysical properties. We find that the latter mechanism is prevalent in these dendrimers. The energy transfer occurs on a picosecond time scale, while the charge-transfer process occurs on a nanosecond time scale. The lifetime of the charge separated species was found to be in the range of microseconds. Energy transfer efficiencies ranging from 80% to 90% were determined using both steady-state and time-resolved measurements, while charge-transfer efficiencies ranging from 70% to 80% were deduced from fluorescence quenching of the core chromophore. The dependence of the energy and charge-transfer processes on dendrimer generation is analyzed in terms of the backfolding of the flexible benzyl ether backbone, which leads to a weaker dependence of the energy and charge-transfer efficiencies on dendrimer size than would be expected for a rigid system.

  DOI：

  10.1021/ja044778m