3-{(1E)-1-[2-(2,4-dinitrophenyl)hydrazinylidene]ethyl}-2H-chromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-{(1E)-1-[2-(2,4-dinitrophenyl)hydrazinylidene]ethyl}-2H-chromen-2-one
• 英文别名: 3-[1-(2,4-dinitro-phenylhydrazono)-ethyl]-coumarin；3-[1-(2,4-Dinitro-phenylhydrazono)-aethyl]-cumarin；3-[N-(2,4-Dinitrophenyl)ethanehydrazonoyl]-2H-chromen-2-one；3-[(E)-N-(2,4-dinitroanilino)-C-methylcarbonimidoyl]chromen-2-one
• 化学式: C₁₇H₁₂N₄O₆
• 分子量: 368.305
• InChiKey: XIECWUPLSHNWQI-VCHYOVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-{(1E)-1-[2-(2,4-dinitrophenyl)hydrazinylidene]ethyl}-2H-chromen-2-one 、 苯酸四丁基铵 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Self assembled pseudo double helix architecture and anion sensing behavior of a coumarin based ICT probe

  摘要：

  The X-ray diffraction (XRD) studies of a coumarin based hydrazone (receptor 1) have revealed self assembled pseudo double helix architecture involving closed shell O-O interactions besides other supramolecular interactions. The receptor (1) an intramolecular charge transfer (ICT) probe detected acetate, benzoate and dihydrogenphosphate through naked-eye in DMSO. The 1:1 stoichiometry was confirmed for all the anions. The (1)H NMR studies indicated classical and non-classical hydrogen bonding through NH and Ar-H protons of the receptor, respectively, during recognition process of the acetate through receptor (1). The theoretical studies through density functional theory (DFT) using B3LYP exchange functional with the basis set 6-311G** supported the UV-vis and (1)H NMR studies. The time dependent density functional theory (TDDFT) computations of UV-vis excitations for the receptor (1) and receptor-acetate complex agreed well with our experimental findings. The cyclic voltammetric studies also supported formation of receptor-acetate complex. (c) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2009.10.040
• 作为产物：
  描述：

  水杨醛 在 哌啶 、 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成 3-{(1E)-1-[2-(2,4-dinitrophenyl)hydrazinylidene]ethyl}-2H-chromen-2-one
  参考文献：
  名称：

  香豆素染料的合成，表征，光学，电化学和电流电压特性。

  摘要：

  合成了一系列具有共同的受体和带有不同供体的π间隔基的香豆素染料，并通过光谱技术对其进行了表征。TiO 2通过溶胶-凝胶法合成了纳米粒子，并通过X射线衍射，扫描电子显微镜和能量色散光谱对其进行了表征。已经研究了光物理和电化学性质。计算了前沿分子轨道（FMO）的带隙，摩尔吸收系数和能量。结果表明，电子释放基团有助于调节带隙。通过密度泛函理论计算获得了FMO的几何优化和能量。计算的全局化学参数有助于理解合成染料分子的固有供体-受体特性。电流-电压特性的结果在照明条件下显示出良好的光电流响应。

  DOI：

  10.1007/s10895-019-02436-7

文献信息

• Dean et al., Journal of the Chemical Society, 1950, p. 895,898
  作者：Dean et al.

  DOI：——

  日期：——
• Synthesis, Characterization, Optical, Electrochemical and Current-Voltage Characteristics of Coumarin Dyes
  作者：K. V. Basavarajappa、Y. Arthoba Nayaka、R. O. Yathisha、P. Manjunatha

  DOI：10.1007/s10895-019-02436-7

  日期：2019.9

  A series of coumarin dyes having common acceptor and pi spacer with different donors were synthesized and characterized by spectroscopic techniques. The TiO2 nanoparticle has been synthesized by sol-gel method and characterized by X-ray diffraction, scanning electron microscopy and energy dispersive spectroscopy. Photophysical and electrochemical properties have been investigated. The band gap, molar

  合成了一系列具有共同的受体和带有不同供体的π间隔基的香豆素染料，并通过光谱技术对其进行了表征。TiO 2通过溶胶-凝胶法合成了纳米粒子，并通过X射线衍射，扫描电子显微镜和能量色散光谱对其进行了表征。已经研究了光物理和电化学性质。计算了前沿分子轨道（FMO）的带隙，摩尔吸收系数和能量。结果表明，电子释放基团有助于调节带隙。通过密度泛函理论计算获得了FMO的几何优化和能量。计算的全局化学参数有助于理解合成染料分子的固有供体-受体特性。电流-电压特性的结果在照明条件下显示出良好的光电流响应。
• Self assembled pseudo double helix architecture and anion sensing behavior of a coumarin based ICT probe
  作者：K.K. Upadhyay、Rakesh K. Mishra、Ajit Kumar、Jianzhang Zhao、Rajendra Prasad

  DOI：10.1016/j.molstruc.2009.10.040

  日期：2010.1

  The X-ray diffraction (XRD) studies of a coumarin based hydrazone (receptor 1) have revealed self assembled pseudo double helix architecture involving closed shell O-O interactions besides other supramolecular interactions. The receptor (1) an intramolecular charge transfer (ICT) probe detected acetate, benzoate and dihydrogenphosphate through naked-eye in DMSO. The 1:1 stoichiometry was confirmed for all the anions. The (1)H NMR studies indicated classical and non-classical hydrogen bonding through NH and Ar-H protons of the receptor, respectively, during recognition process of the acetate through receptor (1). The theoretical studies through density functional theory (DFT) using B3LYP exchange functional with the basis set 6-311G** supported the UV-vis and (1)H NMR studies. The time dependent density functional theory (TDDFT) computations of UV-vis excitations for the receptor (1) and receptor-acetate complex agreed well with our experimental findings. The cyclic voltammetric studies also supported formation of receptor-acetate complex. (c) 2009 Elsevier B.V. All rights reserved.