2-{4-[2-(3,4-dimethoxybenzylidene)hydrazino]phenyl}ethylene-1,1,2-tricarobonitrile | 73664-54-7

• 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: 2-{4-[2-(3,4-dimethoxybenzylidene)hydrazino]phenyl}ethylene-1,1,2-tricarobonitrile
• 英文别名: 2-[4-[2-[(3,4-Dimethoxyphenyl)methylidene]hydrazinyl]phenyl]ethene-1,1,2-tricarbonitrile
• CAS: 73664-54-7
• 化学式: C₂₀H₁₅N₅O₂
• 分子量: 357.371
• InChiKey: JCCHPSKPXIVTJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-(3,4-dimethoxybenzylidene)phenylhydrazine 、 四氰基乙烯 生成 2-{4-[2-(3,4-dimethoxybenzylidene)hydrazino]phenyl}ethylene-1,1,2-tricarobonitrile
  参考文献：
  名称：

  Cyanocarbon Chemistry. XVIII.¹ Tricyanovinylation of Hydrazones and Other Nucleophilic Substances

  摘要：

  DOI：

  10.1021/ja01468a025

文献信息

• Cyanocarbon Chemistry. XVIII.¹ Tricyanovinylation of Hydrazones and Other Nucleophilic Substances
  作者：J. R. Roland、B. C. McKusick

  DOI：10.1021/ja01468a025

  日期：1961.4
• Synthesis, characterization and DFT study of methoxybenzylidene containing chromophores for DSSC materials
  作者：Abdullah G. Al-Sehemi、Ahmad Irfan、Abdullah M. Asiri、Yousry Ahmed Ammar

  DOI：10.1016/j.saa.2012.01.016

  日期：2012.6

  Novel tricyanovinyl derived from hydrazones have been prepared by the reaction of tetracyanoethylene and phenylethylidene hydrazone, and these dyes showed absorption in the region of 539-650 nm. The dyes showed pronounced solvatochromic effects as the polarity of the solvents changed. The torsion in E isomer is smaller than Z and azo isomers of MBD1 and MBD2. The HOMOs are delocalized on whole of the molecule while LUMOs are distributed on the tricarbonitrile. The LUMO energies are above the conduction band of TiO2 and HOMOs of the dyes are below the redox couple of MBD1 and MBD2. The HOMO energies, LUMO energies and HOMO-LUMO energy gap of MBD1 and MBD2 are almost same. The absorption spectra of both the dyes in different solvents are approximately same except in cyclohexane. (C) 2012 Elsevier B.V. All rights reserved.