4,5-bis([1,1′:3′,1″-terphenyl]-2’-yloxy)phthalonitrile | 1221168-49-5

• 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: 4,5-bis([1,1′:3′,1″-terphenyl]-2’-yloxy)phthalonitrile
• 英文别名: 4,5-bis([1,1':3',1"-terphenyl]-2'-yloxy)phthalonitrile；4,5-bis(2′,6′-diphenylphenoxy)phthalonitrile；4,5-bis(2',6'-diphenylphenoxy)phthalonitrile
• CAS: 1221168-49-5
• 化学式: C₄₄H₂₈N₂O₂
• 分子量: 616.719
• InChiKey: ZWRUXHGXWJLOQA-UHFFFAOYSA-N

物化性质

• 沸点：
  741.2±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.68
• 重原子数：
  48.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.04
• 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’-yloxy)phthalonitrile 、 zinc(II) chloride 以 N,N-二甲基乙酰胺 为溶剂， 以30%的产率得到zinc(II) 2,3,9,10,16,17,23,24-octa(2′,6′-diphenylphenoxy)-phthalocyaninato(2-)-N²⁹,N³⁰,N³¹,N³²
  参考文献：
  名称：

  Non-aggregated Zn(ii)octa(2,6-diphenylphenoxy) phthalocyanine as a hole transporting material for efficient perovskite solar cells

  摘要：

  一种非聚集八（2,6-二苯基苯氧基）酞菁锌（代号为 TT80）已被用作过氧化物太阳能电池的空穴传输材料。

  DOI：

  10.1039/c5dt00396b
• 作为产物：
  描述：

  2,6-二苯基苯酚 、 4,5-二氯邻苯二甲腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以54%的产率得到4,5-bis([1,1′:3′,1″-terphenyl]-2’-yloxy)phthalonitrile
  参考文献：
  名称：

  Synthesis and characterization of an A₂BC type phthalocyanine and its visible-light-responsive photocatalytic H₂ production performance on graphitic carbon nitride

  摘要：

  合成和表征A2BC型酞菁及其在石墨烯氮光催化产氢性能方面的可见光响应。

  DOI：

  10.1039/c6dt01248e

文献信息

• Synthesis of zinc phthalocyanine with large steric hindrance and its photovoltaic performance for dye-sensitized solar cells
  作者：Li Lin、Bosi Peng、Wenye Shi、Yingying Guo、Renjie Li

  DOI：10.1039/c4dt03397c

  日期：——

  An asymmetric zinc phthalocyanine with large steric hindrance (Zn-tri-PcNc-8) shows a best efficiency of 3.01%.

  一种具有大的空间位阻的不对称锌酞菁化合物（Zn-tri-PcNc-8）表现出最佳效率为3.01%。
• Asymmetric zinc phthalocyanines with large steric hindrance as efficient red/near-IR responsive sensitizer for dye-sensitized solar cells
  作者：Lijuan Yu、Wenye Shi、Li Lin、Yingying Guo、Renjie Li、Tianyou Peng

  DOI：10.1016/j.dyepig.2014.11.017

  日期：2015.3

  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.
• Enhancement of Incident Photon-to-Current Conversion Efficiency for Phthalocyanine-Sensitized Solar Cells by 3D Molecular Structuralization
  作者：Shogo Mori、Morio Nagata、Yuki Nakahata、Kazumasa Yasuta、Ryota Goto、Mutsumi Kimura、Minoru Taya

  DOI：10.1021/ja9109677

  日期：2010.3.31

  Enlarging the molecular size of zinc phthalocyanine (Pc) dyes three dimensionally with 2,6-diphenylphenoxy substituents significantly reduced the aggregation of the dyes on a TiO(2) surface. As a result, the incident photon-to-current conversion efficiency was improved not only in the Q band but over the whole absorption range, achieving 4.6% energy conversion efficiency under one-sun conditions. Electron Lifetime measurements indicated that these Pc dyes do not enhance charge recombination, encouraging further development of Pc.