2-[(2,6-Dichloro-phenyl)-hydrazono]-malononitrile | 3780-85-6

• 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-[(2,6-Dichloro-phenyl)-hydrazono]-malononitrile
• 英文别名: (2,6-Dichlorophenyl)carbonohydrazonoyl dicyanide；2-[(2,6-dichlorophenyl)hydrazinylidene]propanedinitrile
• CAS: 3780-85-6
• 化学式: C₉H₄Cl₂N₄
• 分子量: 239.064
• InChiKey: WEBDTAJDCTXAPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2,6-Dichloro-phenyl)-hydrazono]-malononitrile 在 copper(II) acetate monohydrate 作用下， 以 乙腈 为溶剂， 反应 28.17h， 生成 2-(2,6-dichlorophenyl)-5-(pyrrolidin-1-yl)-2H-1,2,3-triazole-4-carbonitrile
  参考文献：
  名称：

  2-Aryl-5-amino-1,2,3-triazoles: New effective blue-emitting fluorophores

  摘要：

  The synthesis of a new series of 2-aryl-5-amino-1,2,3-triazole derivatives is reported. The photochemical properties of these new fluorophores were studied both experimentally and using theoretical models. The compounds were found to be fluorescent, with Stokes shifts ranging from 40 nm (2494 CM-1) to 140 nm (9461 cm(-1)) and quantum yield values between 0.004 and 0.996. The fluorescence of the 1,2,3-triazoles was highly structure dependent and could be tuned by variation of the substituents at the C-4 and C-5 atoms of triazole ring and by the electronic and spatial effect of substituents within the aromatic cycle. Photophysical studies showed moderate changes in the fluorescence quantum yields depending on the solvent polarity. The UV-Vis spectra calculations employing the time-dependent density functional theory (TD-DFT) are in good agreement with the experimental data. The favourable photophysical properties of the studied compounds and their facile and high-yielding synthesis make them excellent candidates for commercial application as fluorescent tags. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2016.08.015

文献信息

• Sturdik, Ernest; Durcova, Edita; Mikes, Vladimir, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 11, p. 2819 - 2825
  作者：Sturdik, Ernest、Durcova, Edita、Mikes, Vladimir、Dadak, Vladimir、Balaz, Stefan、et al.

  DOI：——

  日期：——
• 2-Aryl-5-amino-1,2,3-triazoles: New effective blue-emitting fluorophores
  作者：Kseniya D. Gavlik、Ekaterina S. Sukhorukova、Yuri M. Shafran、Pavel A. Slepukhin、Enrico Benassi、Nataliya P. Belskaya

  DOI：10.1016/j.dyepig.2016.08.015

  日期：2017.1

  The synthesis of a new series of 2-aryl-5-amino-1,2,3-triazole derivatives is reported. The photochemical properties of these new fluorophores were studied both experimentally and using theoretical models. The compounds were found to be fluorescent, with Stokes shifts ranging from 40 nm (2494 CM-1) to 140 nm (9461 cm(-1)) and quantum yield values between 0.004 and 0.996. The fluorescence of the 1,2,3-triazoles was highly structure dependent and could be tuned by variation of the substituents at the C-4 and C-5 atoms of triazole ring and by the electronic and spatial effect of substituents within the aromatic cycle. Photophysical studies showed moderate changes in the fluorescence quantum yields depending on the solvent polarity. The UV-Vis spectra calculations employing the time-dependent density functional theory (TD-DFT) are in good agreement with the experimental data. The favourable photophysical properties of the studied compounds and their facile and high-yielding synthesis make them excellent candidates for commercial application as fluorescent tags. (C) 2016 Elsevier Ltd. All rights reserved.