2-nitro-4-carboxy-4'-[N,N-di(2-hydroxyethyl)amino]azobenzene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 2-nitro-4-carboxy-4'-[N,N-di(2-hydroxyethyl)amino]azobenzene
• 英文别名: 4-carboxy-2-nitro-4'-[bis(2-hydroxyethyl)amino]azobenzene
• 化学式: C₁₇H₁₈N₄O₆
• 分子量: 374.353
• InChiKey: XLBMFUXZMIIQOJ-VHEBQXMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  148.86
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-甲氧基乙氧基甲基氯 、 2-nitro-4-carboxy-4'-[N,N-di(2-hydroxyethyl)amino]azobenzene 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以78%的产率得到
  参考文献：
  名称：

  Intermolecular Coupling Enhancement of the Molecular Hyperpolarizability in Multichromophoric Dipolar Dendrons

  摘要：

  Nonlinear optical dendritic macromolecules, called azobenzene dendrons, were synthesized, and their conformational properties and molecular nonlinear optical properties were clarified by second-order nonlinear optical measurement. The synthesized molecules were modified by introducing 1-15 numbers of azobenzene branching units as the nonlinear optical chromophore and by placing aliphatic chains at the end the dendritic chains. In these topologically complex molecules, each chromophore contributed coherently to the macroscopic nonlinear optical activity. The first-order molecular hyperpolarizability of the azobenzene dendron having 15 chromophoric units was measured to be 3010 x 10(-30) esu using the hyper-Rayleigh scattering method. This level of molecular hyperpolarizability was much higher than that For an azobenzene monomer (150 x 10(-30) esu). The polarized nonlinear optical measurement provided structural information on the dendrons and indicated that each chromophore was oriented noncentrosymmetrically along the molecular axis to become a cone shape rather than a spreading or spherical shape. This structure gave rise to a large electronically dipolar macromolecule system, in which each chromophoric unit coherently contributed to the second harmonic generation.

  DOI：

  10.1021/ja993569c
• 作为产物：
  描述：

  N,N-二羟乙基苯胺 、 4-氨基-3-硝基苯甲酸 在 盐酸 、 sodium hydroxide 、 sodium nitrate 作用下， 以 水 、 乙醇 为溶剂， 反应 0.5h， 以57%的产率得到2-nitro-4-carboxy-4'-[N,N-di(2-hydroxyethyl)amino]azobenzene
  参考文献：
  名称：

  在主链和/或侧链中带有偶氮苯部分的光动力学聚合物的光变形行为

  摘要：

  本文描述了在主链和/或侧链中包含推挽式偶氮苯部分的聚合物的比较研究。专门针对这项工作进行了系统地设计和合成，以研究通过聚合物链迁移引起的光致变形，这是由某些聚苯乙烯（PS）球周围产生的光场引起的。通过自组织过程将直径为990 nm的PS球排列在光动力聚合物薄膜的表面上，然后将其暴露在488 nm的线偏振Kr-Ar激光器中。尽管聚合物中的偶氮苯部分显示出非常缓慢的反式-顺式-反式异构化周期，使用原子力显微镜（AFM）成功观察到了一系列六边形排列的凹入结构，这些结构反映了球体的几何形状和排列。这些凹痕的深度与聚合物中偶氮苯部分的动力学一致。分子量，玻璃化转变温度（对于我们使用的所有材料，T g）和在照射光的波长下的吸收率几乎相同。但是，发生在聚合物表面的传质总量并不直接取决于光异构化的效率，而光异构化的效率与聚合物的结构（即主链或侧链类型）更为相关。此外，使用攻丝模式原子力显微镜（TMAFM）

  DOI：

  10.1021/ma034122y

文献信息

• Intermolecular Coupling Enhancement of the Molecular Hyperpolarizability in Multichromophoric Dipolar Dendrons
  作者：Shiyoshi Yokoyama、Tatsuo Nakahama、Akira Otomo、Shinro Mashiko

  DOI：10.1021/ja993569c

  日期：2000.4.1

  Nonlinear optical dendritic macromolecules, called azobenzene dendrons, were synthesized, and their conformational properties and molecular nonlinear optical properties were clarified by second-order nonlinear optical measurement. The synthesized molecules were modified by introducing 1-15 numbers of azobenzene branching units as the nonlinear optical chromophore and by placing aliphatic chains at the end the dendritic chains. In these topologically complex molecules, each chromophore contributed coherently to the macroscopic nonlinear optical activity. The first-order molecular hyperpolarizability of the azobenzene dendron having 15 chromophoric units was measured to be 3010 x 10(-30) esu using the hyper-Rayleigh scattering method. This level of molecular hyperpolarizability was much higher than that For an azobenzene monomer (150 x 10(-30) esu). The polarized nonlinear optical measurement provided structural information on the dendrons and indicated that each chromophore was oriented noncentrosymmetrically along the molecular axis to become a cone shape rather than a spreading or spherical shape. This structure gave rise to a large electronically dipolar macromolecule system, in which each chromophoric unit coherently contributed to the second harmonic generation.
• Photodeformation Behavior of Photodynamic Polymers Bearing Azobenzene Moieties in Their Main and/or Side Chain
  作者：Chang-Dae Keum、Taiji Ikawa、Masaaki Tsuchimori、Osamu Watanabe

  DOI：10.1021/ma034122y

  日期：2003.7.1

  This paper describes a comparative study of polymers containing push−pull type azobenzene moieties in their main and/or side chains. The polymers were systematically designed and synthesized specifically for this work in order to investigate their photodeformation through the migration of polymer chains, which was induced by an optical field generated around some polystyrene (PS) spheres. The PS spheres

  本文描述了在主链和/或侧链中包含推挽式偶氮苯部分的聚合物的比较研究。专门针对这项工作进行了系统地设计和合成，以研究通过聚合物链迁移引起的光致变形，这是由某些聚苯乙烯（PS）球周围产生的光场引起的。通过自组织过程将直径为990 nm的PS球排列在光动力聚合物薄膜的表面上，然后将其暴露在488 nm的线偏振Kr-Ar激光器中。尽管聚合物中的偶氮苯部分显示出非常缓慢的反式-顺式-反式异构化周期，使用原子力显微镜（AFM）成功观察到了一系列六边形排列的凹入结构，这些结构反映了球体的几何形状和排列。这些凹痕的深度与聚合物中偶氮苯部分的动力学一致。分子量，玻璃化转变温度（对于我们使用的所有材料，T g）和在照射光的波长下的吸收率几乎相同。但是，发生在聚合物表面的传质总量并不直接取决于光异构化的效率，而光异构化的效率与聚合物的结构（即主链或侧链类型）更为相关。此外，使用攻丝模式原子力显微镜（TMAFM）