(E)-2-((2,2-diphenylhydrazono)methyl)-1-(hex-5-enyl)-1H-pyrrole | 1219811-88-7

• 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: (E)-2-((2,2-diphenylhydrazono)methyl)-1-(hex-5-enyl)-1H-pyrrole
• CAS: 1219811-88-7
• 化学式: C₂₃H₂₅N₃
• 分子量: 343.472
• InChiKey: XBOCZDFKTOVYJF-HIXSDJFHSA-N

物化性质

• 沸点：
  495.3±47.0 °C(predicted)
• 密度：
  1.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-2-((2,2-diphenylhydrazono)methyl)-1-(hex-5-enyl)-1H-pyrrole 、 方酸 以 甲苯 、 正丁醇 为溶剂， 反应 4.0h， 以52%的产率得到[5-[3-[5-[(diphenylhydrazinylidene)methyl]-1-hex-5-enylpyrrol-1-ium-2-ylidene]-2,4-dioxocyclobutylidene]-1-hex-5-enylpyrrol-2-ylidene]methyl-(N-phenylanilino)azanide
  参考文献：
  名称：

  Marked Alkyl- vs Alkenyl-Substitutent Effects on Squaraine Dye Solid-State Structure, Carrier Mobility, and Bulk-Heterojunction Solar Cell Efficiency

  摘要：

  We report two new squaraine dyes substituted at the pyrrolic rings with n-hexyl (squaraine 1) or n-hexenyl (squaraine 2) chains. Although internal molecular structure variations are minimal, the presence of the terminal double bond results in a much more compact solid-state structure, dramatically affecting charge transport in the thin films; the hole mobility of 2 is similar to 5x that of 1, and the BHJ OPV power conversion efficiency (PCE) of 2 is similar to 2x that of 1. PCEs surpassing 2% for ambient solution-processed devices are demonstrated, the largest so far achieved for squaraine-based organic solar cells.

  DOI：

  10.1021/ja100520q
• 作为产物：
  描述：

  N-(hex-5-enyl)pyrrole-2-carbaldehyde 、 1,1-二苯肼盐酸盐 在 咪唑 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以77%的产率得到(E)-2-((2,2-diphenylhydrazono)methyl)-1-(hex-5-enyl)-1H-pyrrole
  参考文献：
  名称：

  Marked Alkyl- vs Alkenyl-Substitutent Effects on Squaraine Dye Solid-State Structure, Carrier Mobility, and Bulk-Heterojunction Solar Cell Efficiency

  摘要：

  We report two new squaraine dyes substituted at the pyrrolic rings with n-hexyl (squaraine 1) or n-hexenyl (squaraine 2) chains. Although internal molecular structure variations are minimal, the presence of the terminal double bond results in a much more compact solid-state structure, dramatically affecting charge transport in the thin films; the hole mobility of 2 is similar to 5x that of 1, and the BHJ OPV power conversion efficiency (PCE) of 2 is similar to 2x that of 1. PCEs surpassing 2% for ambient solution-processed devices are demonstrated, the largest so far achieved for squaraine-based organic solar cells.

  DOI：

  10.1021/ja100520q