4-(4-nitrobenzylideneamino)-2,6-diphenylphenol | 1263417-95-3

• 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: 4-(4-nitrobenzylideneamino)-2,6-diphenylphenol
• 英文别名: 4-[(4-Nitrophenyl)methylideneamino]-2,6-diphenylphenol；4-[(4-nitrophenyl)methylideneamino]-2,6-diphenylphenol
• CAS: 1263417-95-3
• 化学式: C₂₅H₁₈N₂O₃
• 分子量: 394.43
• InChiKey: FQELGSQWHVUXIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-nitrobenzylideneamino)-2,6-diphenylphenol 在 四丁基氢氧化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 C₂₅H₁₇N₂O₃^(1-)
  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
• 作为产物：
  描述：

  4-氨基-2,6-二苯基苯酚 、 对硝基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以16%的产率得到4-(4-nitrobenzylideneamino)-2,6-diphenylphenol
  参考文献：
  名称：

  基于 4-(4-硝基亚苄基胺)-2,6-二苯基苯酚的阴离子显色化学传感器用于选择性检测乙腈-水混合物中的氰化物

  摘要：

  Nitrobenzylideneamine)-2,6-diphenylphenol 3a 被合成并作为阴离子显色化学传感器进行研究。3a 在乙腈中的溶液是无色的，但在去质子化作用下会变成蓝色。从添加到 3a 溶液中的各种阴离子中，只有 CN - 、F - 以及强度较低的 CH3COO - 和 H2PO4 - 导致溶液有色。添加高达 2.4% (v/v) 的水后，在所有使用的阴离子中，仅 CN - 能够充当碱并导致溶液颜色发生变化。基于两种 3a:阴离子化学计量比，1:1 和 1:2，使用模型来解释结果。

  DOI：

  10.3998/ark.5550190.0011.b13

文献信息

• An anionic chromogenic chemosensor based on 4–(4–nitrobenzylideneamine)–2,6–diphenylphenol for selective detection of cyanide in acetonitrile–water mixtures
  作者：Vanderléia G. Marini、Eliane Torri、Lizandra M. Zimmermann、Vanderlei G. Machado

  DOI：10.3998/ark.5550190.0011.b13

  日期：——

  Nitrobenzylideneamine)-2,6-diphenylphenol 3a was synthesized and studied as an anionic chromogenic chemosensor. Solutions of 3a in acetonitrile are colorless but turn blue under deprotonation. From the various anions added to the solutions of 3a only CN - , F - , and with less intensity CH3COO - and H2PO4 - , led to colored solutions. With the addition of up to 2.4% (v/v) of water, of all the anions

  Nitrobenzylideneamine)-2,6-diphenylphenol 3a 被合成并作为阴离子显色化学传感器进行研究。3a 在乙腈中的溶液是无色的，但在去质子化作用下会变成蓝色。从添加到 3a 溶液中的各种阴离子中，只有 CN - 、F - 以及强度较低的 CH3COO - 和 H2PO4 - 导致溶液有色。添加高达 2.4% (v/v) 的水后，在所有使用的阴离子中，仅 CN - 能够充当碱并导致溶液颜色发生变化。基于两种 3a:阴离子化学计量比，1:1 和 1:2，使用模型来解释结果。
• 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.