1,3-dioxo-2-phenyl-2,3-dihydro-1H-benzo[f]isoindole-6,7-dicarbonitrile | 56025-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1,3-dioxo-2-phenyl-2,3-dihydro-1H-benzo[f]isoindole-6,7-dicarbonitrile
• 英文别名: 1,3-dioxo-2-phenyl-2,3-dihydro-1H-benzo[f]isoindole-6,7-dicarbonitrile；6,7-Dicyano-naphthalin-2,3-dicarbonsaeure-N-phenyl-imid
• CAS: 56025-80-0
• 化学式: C₂₀H₉N₃O₂
• 分子量: 323.31
• InChiKey: ZVEIIMVCSVHRBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,5-bis([1,1':3′,1"-terphenyl]-2'-ylthio)phthalonitrile 、 zinc(II) acetate dihydrate 、 1,3-dioxo-2-phenyl-2,3-dihydro-1H-benzo[f]isoindole-6,7-dicarbonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 戊醇 为溶剂， 反应 12.0h， 以7.8%的产率得到
  参考文献：
  名称：

  Asymmetric zinc phthalocyanines with large steric hindrance as efficient red/near-IR responsive sensitizer for dye-sensitized solar cells

  摘要：

  Asymmetric ZnPc derivatives with two carboxyl and six diphenylphenoxy or diphenylthiophenol groups were synthesized as dye of DSSCs. Those ZnPcs exhibit strong red/near-IR light absorption, and Zn-tri-PcNc-5 with six diphenylthiophenol groups shows obvious redshift in the Q-band and enhanced absorbance compared to Zn-tri-PcNc-4 with six diphenylphenoxy groups, while Zn-tri-PcNc-4 yielded a 3.22% efficiency in sensitizing TiO2-based solar cell, much higher than that (1.30%) of the S-substituted analog (Zn-tri-PcNc-5). The decreased efficiency of Zn-tri-PcNc-5 is due to the molecular orbital shift to negative direction, stemmed from S atoms instead of O atoms in the six substituents of Zn-tri-PcNc-4, which leads to insufficient driving force for the electron injection. The present results demonstrate that the optimization of molecular orbital levels of ZnPcs via changing the substituents' "push-pull" effect is an effective approach to improve the ZnPc-sensitized cell performance. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.11.017