| 1421611-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1421611-44-0
• 化学式: C₁₃H₈N₃O₅
• 分子量: 286.224
• InChiKey: VITPGJGEJVBBKN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121.7
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2'.4'-Dinitrobenzyliden-4-hydroxyanilin 在 四丁基氢氧化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  Nitro-Substituted 4-[(Phenylmethylene)imino]phenolates: Solvatochromism and Their Use as Solvatochromic Switches and as Probes for the Investigation of Preferential Solvation in Solvent Mixtures

  摘要：

  Four 4-[[(4-nitrophenyl)methylene]imino]phenols (2a-d) were synthesized. After deprotonation in solution, they formed the solvatochromic phenolates 3a-d, which revealed a reversal in solvatochromism. Their UV-vis spectroscopic behavior was explained on the basis of the interaction Of the dyes with the medium through combined effects, such as nonspecific solute-solvent interactions and hydrogen bonding between the solvents and the nitro and phenolate groups. Dyes 3a-c were used as probes to investigate binary solvent mixtures, and the synergistic behavior observed was attributed to solvent-solvent and solute-solvent interactions. A very unusual UV-vis spectroscopic behavior occurred with dye 3d, which has in its molecular structure two nitro substituents as acceptor groups and two phenyl groups on the phenolate moiety. In alcohol/water mixtures, the E-T(3d) values increase from pure alcohol (methanol, ethanol, and propan-2-ol) until the addition of up to 80-96% Water. Subsequently, the addition of a small amount of water causes a very sharp reduction in the E-T(3d) value (for methanol, this corresponds to a bathochromic shift from 543 to 732 nm). This represents the first example of a solvatochromic switch triggered by a subtle change in the polarity of the medium, the color of the solutions being easily reversed by adding small amounts of the required cosolvent.

  DOI：

  10.1021/jo301890r

文献信息

• Nitro-Substituted 4-[(Phenylmethylene)imino]phenolates: Solvatochromism and Their Use as Solvatochromic Switches and as Probes for the Investigation of Preferential Solvation in Solvent Mixtures
  作者：Leandro G. Nandi、Felipe Facin、Vanderléia G. Marini、Lizandra M. Zimmermann、Luciano A. Giusti、Robson da Silva、Giovanni F. Caramori、Vanderlei G. Machado

  DOI：10.1021/jo301890r

  日期：2012.12.7

  Four 4-[[(4-nitrophenyl)methylene]imino]phenols (2a-d) were synthesized. After deprotonation in solution, they formed the solvatochromic phenolates 3a-d, which revealed a reversal in solvatochromism. Their UV-vis spectroscopic behavior was explained on the basis of the interaction Of the dyes with the medium through combined effects, such as nonspecific solute-solvent interactions and hydrogen bonding between the solvents and the nitro and phenolate groups. Dyes 3a-c were used as probes to investigate binary solvent mixtures, and the synergistic behavior observed was attributed to solvent-solvent and solute-solvent interactions. A very unusual UV-vis spectroscopic behavior occurred with dye 3d, which has in its molecular structure two nitro substituents as acceptor groups and two phenyl groups on the phenolate moiety. In alcohol/water mixtures, the E-T(3d) values increase from pure alcohol (methanol, ethanol, and propan-2-ol) until the addition of up to 80-96% Water. Subsequently, the addition of a small amount of water causes a very sharp reduction in the E-T(3d) value (for methanol, this corresponds to a bathochromic shift from 543 to 732 nm). This represents the first example of a solvatochromic switch triggered by a subtle change in the polarity of the medium, the color of the solutions being easily reversed by adding small amounts of the required cosolvent.