4,7-bis(5-(3-hydroxyphenyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole | 840531-02-4

• 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-hydroxyphenyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole
• 英文别名: 3-[5-[4-[5-(3-Hydroxyphenyl)thiophen-2-yl]-2,1,3-benzothiadiazol-7-yl]thiophen-2-yl]phenol
• CAS: 840531-02-4
• 化学式: C₂₆H₁₆N₂O₂S₃
• 分子量: 484.623
• InChiKey: HDASVKWXGYXAFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3-{3-[3-(Phenyl-pyren-1-yl-amino)-benzyloxy]-benzyloxy}-phenyl)-methanol 、 4,7-bis(5-(3-hydroxyphenyl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以72%的产率得到N-phenyl-N-[3-[[3-[[3-[[3-[5-[4-[5-[3-[[3-[[3-[[3-(N-pyren-1-ylanilino)phenyl]methoxy]phenyl]methoxy]phenyl]methoxy]phenyl]thiophen-2-yl]-2,1,3-benzothiadiazol-7-yl]thiophen-2-yl]phenoxy]methyl]phenoxy]methyl]phenoxy]methyl]phenyl]pyren-1-amine
  参考文献：
  名称：

  Dendrimer Analogues of Linear Molecules to Evaluate Energy and Charge-Transfer Properties

  摘要：

  We have designed and synthesized difunctionalized dendrimers containing two donors in the periphery and an acceptor at the core to serve as scaffolds for comparison with linear analogues to investigate the advantage of dendritic scaffolds for energy and charge transfer. Comparison of these dendrimers with the fully decorated dendrimers provides information on the advantage of chromophore density in energy/charge transfer from periphery to the core.

  DOI：

  10.1021/ol0608956
• 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 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 4,7-bis(5-(3-hydroxyphenyl)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

• Nantalaksakul, Arpornrat; Mueller, Astrid; Klaikherd, Akamol, Journal of the American Chemical Society, 2009, vol. 131, p. 2727 - 2738
  作者：Nantalaksakul, Arpornrat、Mueller, Astrid、Klaikherd, Akamol、Bardeen, Christopher J.、Thayumanavan, S.

  DOI：——

  日期：——