7-{(7-bromo-10-hexyl-10H-phenothiazin-3-yl)ethen-3-yl}-10-hexyl-10H-phenothiazine-3-carboxaldehyde | 1379802-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 7-{(7-bromo-10-hexyl-10H-phenothiazin-3-yl)ethen-3-yl}-10-hexyl-10H-phenothiazine-3-carboxaldehyde
• 英文别名: 7-[(E)-2-(7-bromo-10-hexylphenothiazin-3-yl)ethenyl]-10-hexylphenothiazine-3-carbaldehyde
• CAS: 1379802-53-5
• 化学式: C₃₉H₄₁BrN₂OS₂
• 分子量: 697.803
• InChiKey: INDUMOOKQLCQDY-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-{(7-bromo-10-hexyl-10H-phenothiazin-3-yl)ethen-3-yl}-10-hexyl-10H-phenothiazine-3-carboxaldehyde 在 哌啶 、 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 3-[7-[[7-[{4-(N,N-Diphenylamino)phenyl}ethen-3-yl]-10-hexyl-10H-phenothiazinyl]-ethen-3-yl]-10-hexyl-10H-phenothiazin-3-yl]-2-cyanoacrylic acid
  参考文献：
  名称：

  Tuning of spacer groups in organic dyes for efficient inhibition of charge recombination in dye-sensitized solar cells

  摘要：

  Most of the studied organic dyes for dye-sensitized solar cell have exhibited low photovoltage due to fast charge recombination. Here, we report on synthetic strategy of organic dye to get high photovoltage. Phenothiazine (PTZ) moieties are incorporated between electron donating triphenylamine (D) and electron accepting cyanoacrylic acid (A) to enhance non-planarity. Compared to one PTZ incorporation (D-PTZ-A), hypsochromic shift in absorption is observed by incorporation of two PTZs (D-PTZ1 PTZ2-A) due to transition from HOMO-1 to LUMO as confirmed by density functional theory (DFT) calculation. D-PTZ1-PTZ2-A shows higher photovoltage (0.804 V) than D-PTZ-A (0.781 V), those which are even higher than that of the ruthenium-based N719-snesitized one (0.775 V). Little difference in electron transport rate is observed for PTZ derivatives and N719, while electron life time is increased in the order of D-PTZ1-PTZ2-A > D-PTZ-A > N719. Retardation of electron recombination is responsible for the high photovoltage, which is associated with bent conformation induced by PTZ spacer group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.04.002
• 作为产物：
  描述：

  7-{(10-hexyl-10H-phenothiazin-3-yl)ethen-3-yl}-10-hexyl-10H-phenothiazine-3-carboxaldehyde 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以67.8%的产率得到7-{(7-bromo-10-hexyl-10H-phenothiazin-3-yl)ethen-3-yl}-10-hexyl-10H-phenothiazine-3-carboxaldehyde
  参考文献：
  名称：

  Tuning of spacer groups in organic dyes for efficient inhibition of charge recombination in dye-sensitized solar cells

  摘要：

  Most of the studied organic dyes for dye-sensitized solar cell have exhibited low photovoltage due to fast charge recombination. Here, we report on synthetic strategy of organic dye to get high photovoltage. Phenothiazine (PTZ) moieties are incorporated between electron donating triphenylamine (D) and electron accepting cyanoacrylic acid (A) to enhance non-planarity. Compared to one PTZ incorporation (D-PTZ-A), hypsochromic shift in absorption is observed by incorporation of two PTZs (D-PTZ1 PTZ2-A) due to transition from HOMO-1 to LUMO as confirmed by density functional theory (DFT) calculation. D-PTZ1-PTZ2-A shows higher photovoltage (0.804 V) than D-PTZ-A (0.781 V), those which are even higher than that of the ruthenium-based N719-snesitized one (0.775 V). Little difference in electron transport rate is observed for PTZ derivatives and N719, while electron life time is increased in the order of D-PTZ1-PTZ2-A > D-PTZ-A > N719. Retardation of electron recombination is responsible for the high photovoltage, which is associated with bent conformation induced by PTZ spacer group. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.04.002