6-[4-[(4-methoxyphenyl)azo]phenoxy]hexanoic acid | 89763-59-7

• 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: 6-[4-[(4-methoxyphenyl)azo]phenoxy]hexanoic acid
• 英文别名: 6-[4-[(4-Methoxyphenyl)diazenyl]phenoxy]hexanoic acid
• CAS: 89763-59-7
• 化学式: C₁₉H₂₂N₂O₄
• 分子量: 342.395
• InChiKey: TWOQZEYLNDJCQS-UHFFFAOYSA-N

物化性质

• 沸点：
  547.3±35.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  80.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-[4-[(4-methoxyphenyl)azo]phenoxy]hexanoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到6-[4-[(4-methoxyphenyl)azo]phenoxy]hexanoyl chloride
  参考文献：
  名称：

  Stable Holographic Gratings with Small-Molecular Trisazobenzene Derivatives

  摘要：

  We present a series of small-molecular trisazobenzene chromophores, including, for instance, 1,3,5-tris{[4-[4-[(4-cyanophenyl)azo]phenoxy)butyryl]amino}benzene that feature a remarkably stable light-induced orientation in initially amorphous thin-film architectures. It is demonstrated that for optimal performance it is critical to design chemical structures that allow formation of both an amorphous and a liquid-crystalline phase. In the present approach, the liquid-crystal line feature was introduced by inserting decoupling spacers between a trisfunctionalized benzene core and the three azobenzene moieties, as well as adding polar end groups to the latter. To compensate for the deleterious reduction of the glass transition temperature associated with the spacers in the compounds, polar units were incorporated between the benzene core and the side groups. Intriguingly, the molecular glasses that feature a latent liquid-crystal line phase display a remarkable "postdevelopment", i.e., an increase of the amplitude of refractive index modulation in holographic experiments after writing of optical gratings is arrested, exceeding 20% for the previously mentioned derivative. Thus, these nonpolymeric, azobenzene-containing compounds presented in this work appear to be attractive candidates for fabrication of stable holographic volume gratings.

  DOI：

  10.1021/ja9091038
• 作为产物：
  描述：

  6-[4-[(4-methoxyphenyl)azo]phenoxy]hexanoic acid ethyl ester 在 盐酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 6-[4-[(4-methoxyphenyl)azo]phenoxy]hexanoic acid
  参考文献：
  名称：

  具有异常可逆形状变化的新型侧链液晶弹性体。

  摘要：

  液晶弹性体（LCE）已作为刺激控制的执行器和软机器人进行了积极研究。这些应用的基础是LCE在液晶（LC）-各向同性相变时经历可逆形状变化的能力。本文中，我们报告了基于侧链液晶聚合物（SCLCP）的新型LCE的合成。与已知的LCE相比，此LCE表现出惊人的异常形状变化。使机械拉伸的单畴带材经历LC无序相变，带材的长度和宽度均在各向同性相中收缩，并且在LC相中均伸长。这种热诱导行为是沿拉伸方向取向的聚合物主链的松弛与垂直于拉伸方向取向的侧基介晶无序之间微妙相互作用的结果。这一发现指出了这种特殊类型的LCE的潜在设计以及可能利用的应用。

  DOI：

  10.1002/anie.202003904

文献信息

• Stable Holographic Gratings with Small-Molecular Trisazobenzene Derivatives
  作者：Klaus Kreger、Pascal Wolfer、Hubert Audorff、Lothar Kador、Natalie Stingelin-Stutzmann、Paul Smith、Hans-Werner Schmidt

  DOI：10.1021/ja9091038

  日期：2010.1.20

  We present a series of small-molecular trisazobenzene chromophores, including, for instance, 1,3,5-tris[4-[4-[(4-cyanophenyl)azo]phenoxy)butyryl]amino}benzene that feature a remarkably stable light-induced orientation in initially amorphous thin-film architectures. It is demonstrated that for optimal performance it is critical to design chemical structures that allow formation of both an amorphous and a liquid-crystalline phase. In the present approach, the liquid-crystal line feature was introduced by inserting decoupling spacers between a trisfunctionalized benzene core and the three azobenzene moieties, as well as adding polar end groups to the latter. To compensate for the deleterious reduction of the glass transition temperature associated with the spacers in the compounds, polar units were incorporated between the benzene core and the side groups. Intriguingly, the molecular glasses that feature a latent liquid-crystal line phase display a remarkable "postdevelopment", i.e., an increase of the amplitude of refractive index modulation in holographic experiments after writing of optical gratings is arrested, exceeding 20% for the previously mentioned derivative. Thus, these nonpolymeric, azobenzene-containing compounds presented in this work appear to be attractive candidates for fabrication of stable holographic volume gratings.
• A Novel Side‐Chain Liquid Crystal Elastomer Exhibiting Anomalous Reversible Shape Change
  作者：Lu Yin、Li Han、Feijie Ge、Xia Tong、Wei Zhang、Armand Soldera、Yue Zhao

  DOI：10.1002/anie.202003904

  日期：2020.8.24

  Liquid crystalline elastomers (LCEs) have been actively investigated as stimuli‐controlled actuators and soft robots. The basis of these applications is the ability of LCEs to undergo a reversible shape change upon a liquid crystalline (LC)‐isotropic phase transition. Herein, we report the synthesis of a novel LCE based on a side‐chain liquid crystalline polymer (SCLCP). In contrast to known LCEs,

  液晶弹性体（LCE）已作为刺激控制的执行器和软机器人进行了积极研究。这些应用的基础是LCE在液晶（LC）-各向同性相变时经历可逆形状变化的能力。本文中，我们报告了基于侧链液晶聚合物（SCLCP）的新型LCE的合成。与已知的LCE相比，此LCE表现出惊人的异常形状变化。使机械拉伸的单畴带材经历LC无序相变，带材的长度和宽度均在各向同性相中收缩，并且在LC相中均伸长。这种热诱导行为是沿拉伸方向取向的聚合物主链的松弛与垂直于拉伸方向取向的侧基介晶无序之间微妙相互作用的结果。这一发现指出了这种特殊类型的LCE的潜在设计以及可能利用的应用。