1,2-bis(2-acetoxybenzamido)benzene | 41350-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-bis(2-acetoxybenzamido)benzene
• CAS: 41350-19-0
• 化学式: C₂₄H₂₀N₂O₆
• 分子量: 432.433
• InChiKey: UQSXDWGYZNGQCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  110.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  硝基甲烷 、 1,2-bis(2-acetoxybenzamido)benzene 在 sodium hydroxide 、 盐酸 作用下， 以 水 、 丙酮 为溶剂， 以77%的产率得到2-羟基-N-[2-[(2-羟基苯甲酰基)氨基]苯基]苯甲酰胺
  参考文献：
  名称：

  Oxidovanadium(IV/V) Complexes as New Redox Mediators in Dye-Sensitized Solar Cells: A Combined Experimental and Theoretical Study

  摘要：

  Corrosiveness is one of the main drawbacks of using the iodide/triiodide redox couple in dye-sensitized solar cells (DSSCs). Alternative redox couples including transition metal complexes have been investigated where surprisingly high efficiencies for the conversion of solar to electrical energy have been achieved. In this paper, we examined the development of a DSSC using an electrolyte based on square pyramidal oxidovanadium(IV/V) complexes. The oxidovanadium(IV) complex (Ph4P)(2)[(VO)-O-IV(hybeb)] was combined with its oxidized analogue (Ph4P)[V-VO(hybeb)] {where hybeb4 is the tetradentate diamidodiphenolate ligand [1-(2-hydroxybenzamido)-2-(2-pyridinecarboxamido)benzenato}and applied as a redox couple in the electrolyte of DSSCs. The complexes exhibit large electron exchange and transfer rates, which are evident from electron paramagnetic resonance spectroscopy and electrochemistry, rendering the oxidovanadium(IV/V) compounds suitable for redox mediators in DSSCs. The very large self-exchange rate constant offered an insight into the mechanism of the exchange reaction most likely mediated through an outer-sphere exchange mechanism. The [V-IVO(hybeb)](2)(-)/[V-VO(hybeb)](-) redox potential and the energy of highest occupied molecular orbital (HOMO) of the sensitizing dye N719 and the HOMO of [V-IVO(hybeb)](2-) were calculated by means of density functional theory electronic structure calculation methods. The complexes were applied as a new redox mediator in DSSCs, while the cell performance was studied in terms of the concentration of the reduced and oxidized form of the complexes. These studies were performed with the commercial Ru-based sensitizer N719 absorbed on a TiO2 semiconducting film in the DSSC. Maximum energy conversion efficiencies of 2% at simulated solar light (AM 1.5; 1000 W m(-2)) with an open circuit voltage of 660 mV, a short-circuit current of 5.2 mA cm(-2), and a fill factor of 0.58 were recorded without the presence of any additives in the electrolyte.

  DOI：

  10.1021/acs.inorgchem.5b00159
• 作为产物：
  描述：

  邻苯二胺 、 邻乙酰水杨酰氯 以 四氢呋喃 为溶剂， 反应 18.0h， 以80%的产率得到1,2-bis(2-acetoxybenzamido)benzene
  参考文献：
  名称：

  Oxidovanadium(IV/V) Complexes as New Redox Mediators in Dye-Sensitized Solar Cells: A Combined Experimental and Theoretical Study

  摘要：

  Corrosiveness is one of the main drawbacks of using the iodide/triiodide redox couple in dye-sensitized solar cells (DSSCs). Alternative redox couples including transition metal complexes have been investigated where surprisingly high efficiencies for the conversion of solar to electrical energy have been achieved. In this paper, we examined the development of a DSSC using an electrolyte based on square pyramidal oxidovanadium(IV/V) complexes. The oxidovanadium(IV) complex (Ph4P)(2)[(VO)-O-IV(hybeb)] was combined with its oxidized analogue (Ph4P)[V-VO(hybeb)] {where hybeb4 is the tetradentate diamidodiphenolate ligand [1-(2-hydroxybenzamido)-2-(2-pyridinecarboxamido)benzenato}and applied as a redox couple in the electrolyte of DSSCs. The complexes exhibit large electron exchange and transfer rates, which are evident from electron paramagnetic resonance spectroscopy and electrochemistry, rendering the oxidovanadium(IV/V) compounds suitable for redox mediators in DSSCs. The very large self-exchange rate constant offered an insight into the mechanism of the exchange reaction most likely mediated through an outer-sphere exchange mechanism. The [V-IVO(hybeb)](2)(-)/[V-VO(hybeb)](-) redox potential and the energy of highest occupied molecular orbital (HOMO) of the sensitizing dye N719 and the HOMO of [V-IVO(hybeb)](2-) were calculated by means of density functional theory electronic structure calculation methods. The complexes were applied as a new redox mediator in DSSCs, while the cell performance was studied in terms of the concentration of the reduced and oxidized form of the complexes. These studies were performed with the commercial Ru-based sensitizer N719 absorbed on a TiO2 semiconducting film in the DSSC. Maximum energy conversion efficiencies of 2% at simulated solar light (AM 1.5; 1000 W m(-2)) with an open circuit voltage of 660 mV, a short-circuit current of 5.2 mA cm(-2), and a fill factor of 0.58 were recorded without the presence of any additives in the electrolyte.

  DOI：

  10.1021/acs.inorgchem.5b00159