4,7-bis(5-(3-(benzyloxy)phenyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole | 840531-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,7-bis(5-(3-(benzyloxy)phenyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole
• 英文别名: 4,7-Bis{5-[3-(benzyloxy)phenyl]thiophen-2-yl}-2,1,3-benzothiadiazole；4,7-bis[5-(3-phenylmethoxyphenyl)thiophen-2-yl]-2,1,3-benzothiadiazole
• CAS: 840531-14-8
• 化学式: C₄₀H₂₈N₂O₂S₃
• 分子量: 664.873
• InChiKey: VHMOWKAMXZNROO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,7-双(5-溴-2-噻吩基)-2,1,3-苯并噻二唑 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 4,7-bis(5-(3-(benzyloxy)phenyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole
  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

文献信息

• Energy and Electron Transfer in Bifunctional Non-Conjugated Dendrimers
  作者：K. R. Justin Thomas、Alexis L. Thompson、Aathimanikandan V. Sivakumar、Christopher J. Bardeen、S. Thayumanavan

  DOI：10.1021/ja044778m

  日期：2005.1.1

  \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.