2-{4-[2-(4-nitrobenzylidene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile | 94803-15-3

• 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: 2-{4-[2-(4-nitrobenzylidene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile
• 英文别名: (4-{2-[(4-Nitrophenyl)methylidene]hydrazinyl}phenyl)ethene-1,1,2-tricarbonitrile；2-[4-[2-[(4-nitrophenyl)methylidene]hydrazinyl]phenyl]ethene-1,1,2-tricarbonitrile
• CAS: 94803-15-3
• 化学式: C₁₈H₁₀N₆O₂
• 分子量: 342.316
• InChiKey: MTTPPTPTISQBAA-UHFFFAOYSA-N

物化性质

• 沸点：
  549.7±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  四氰基乙烯 、 4-nitro-benzaldehyde phenylhydrazone 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以70%的产率得到2-{4-[2-(4-nitrobenzylidene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile
  参考文献：
  名称：

  Molecular design of new hydrazone dyes for dye-sensitized solar cells: Synthesis, characterization and DFT study

  摘要：

  Three new sensitizers 2-{4-[2-(4-Nitrobenzylidene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile (NBHPET), 2-{4-[2-p-Chlorobenzylidenehydrazino]phenyl}- ethylene-1,1,2-tri carbonitrile (CBHPET) and 2-{4-[2-p-Bromobenzylidenehydrazino] phenyl}ethylene-1,1,2-tricarbonitrile (BBHPET) have been synthesized. The dyes showed pronounced solvatochromic effects as the polarity of the solvents increased. The structures have been optimized at B3LYP/6-31G(d) level of theory. The torsion in E-isomer is smaller than Z-isomer and azo isomers. The highest occupied molecular orbitals are delocalized on whole molecule while lowest unoccupied molecular orbitals are distributed on the tricarbonitrile. The lowest unoccupied molecular orbital energies are above the conduction band of titanium dioxide, highest occupied molecular orbitals of the dyes are below the redox couple of new synthesized dyes and small energy gap revealed these dyes would be better sensitizers for dye-sensitized solar cells. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2012.02.035

文献信息

• Molecular design of new hydrazone dyes for dye-sensitized solar cells: Synthesis, characterization and DFT study
  作者：Abdullah G. Al-Sehemi、Ahmad Irfan、Abdullah M. Asiri、Yousry Ahmed Ammar

  DOI：10.1016/j.molstruc.2012.02.035

  日期：2012.7

  Three new sensitizers 2-4-[2-(4-Nitrobenzylidene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile (NBHPET), 2-4-[2-p-Chlorobenzylidenehydrazino]phenyl}- ethylene-1,1,2-tri carbonitrile (CBHPET) and 2-4-[2-p-Bromobenzylidenehydrazino] phenyl}ethylene-1,1,2-tricarbonitrile (BBHPET) have been synthesized. The dyes showed pronounced solvatochromic effects as the polarity of the solvents increased. The structures have been optimized at B3LYP/6-31G(d) level of theory. The torsion in E-isomer is smaller than Z-isomer and azo isomers. The highest occupied molecular orbitals are delocalized on whole molecule while lowest unoccupied molecular orbitals are distributed on the tricarbonitrile. The lowest unoccupied molecular orbital energies are above the conduction band of titanium dioxide, highest occupied molecular orbitals of the dyes are below the redox couple of new synthesized dyes and small energy gap revealed these dyes would be better sensitizers for dye-sensitized solar cells. (C) 2012 Elsevier B.V. All rights reserved.