4-[(4-methoxy)-phenylazo]benzoyl chloride

• 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: 4-[(4-methoxy)-phenylazo]benzoyl chloride
• 英文别名: 4-[(4-Methoxyphenyl)diazenyl]benzoyl chloride；4-[(4-methoxyphenyl)diazenyl]benzoyl chloride
• 化学式: C₁₄H₁₁ClN₂O₂
• 分子量: 274.707
• InChiKey: VKESBJYMYJTASM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  间苯三酚 、 4-[(4-methoxy)-phenylazo]benzoyl chloride 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到1,3,5-tris{[4-[(4-methoxyphenyl)azo]benzoyl]oxy}benzene
  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：

  4-methoxy-4'-carboxylic azobenzene 在 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 4-[(4-methoxy)-phenylazo]benzoyl chloride
  参考文献：
  名称：

  4-（4'-烷氧基苯基偶氮）苯甲酰氯不仅是中间体，而且是用于光开关的光敏液晶元

  摘要：

  本文介绍了我们对4-（4'-烷氧基苯基偶氮）苯甲酰氯的完全同源系列的研究结果。迄今为止，这些化合物仅用作更复杂材料的中间体，尚未研究其性能，因为酰基氯被认为是不稳定的，因此在应用中无用。我们证明它们实际上很耐久，并在很宽的温度范围内具有液晶性能。此外，该系列还证明了顺式-反式异构化的快速切换时间少于一个小时的弛豫时间，这使得这些化合物有望成为光学切换的材料。

  DOI：

  10.1016/j.molliq.2016.11.014

文献信息

• Holographic Investigations of Azobenzene-Containing Low-Molecular-Weight Compounds in Pure Materials and Binary Blends with Polystyrene
  作者：Hubert Audorff、Roland Walker、Lothar Kador、Hans-Werner Schmidt

  DOI：10.1002/chem.201100941

  日期：2011.11.4

  photochromic low‐molecular‐weight compounds, especially with respect to the formation of holographic volume gratings in the pure materials and in binary blends with polystyrene. Its aim is to provide a basic understanding of the holographic response with regard to the molecular structure, and thus to show a way to obtain suitable rewritable materials with high sensitivity for holographic data storage

  本文报道了光致变色低分子量化合物的合成及其热学和光学性质，特别是在纯材料中以及与聚苯乙烯的二元共混物中形成全息体积光栅方面。其目的是提供关于分子结构的全息响应的基本理解，从而显示出一种获得合适的可重写材料且对全息数据存储具有高灵敏度的方法。光活性低分子量化合物由一个中心核和三个或四个通过酯化连接的基于偶氮苯的臂组成。研究了影响玻璃化转变温度和玻璃形成特性的四个不同的核。偶氮苯生色团上的极性末端取代基引入了其他结构变化，以微调光学性质和全息响应。在全息实验中对纯化合物的薄膜进行了研究，特别是在材料敏感性方面。在低分子量化合物与聚苯乙烯的二元共混物中，研究了聚合物基质对全息实验行为的影响。还在高温下研究了最有希望的材料组合，在该温度下，全息记录的灵敏度甚至更高。在低分子量化合物与聚苯乙烯的二元共混物中，研究了聚合物基质对全息实验行为的影响。还在高温下研究了最有希望的材料组合，在该温度下，全息记
• Wang; Li, Polish Journal of Chemistry, 2001, vol. 75, # 5, p. 699 - 706
  作者：Wang、Li

  DOI：——

  日期：——
• Wang; Li, Polish Journal of Chemistry, <hi>2001</hi>, vol. 75, # 5, p. 699 - 706
  作者：Wang、Li

  DOI：——

  日期：——
• 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.
• 4-(4′-Alkyloxyphenylazo)benzoyl chlorides not only intermediates but photosensitive mesogens for optical switching
  作者：Joanna Jaworska、Izabela Korbecka、Andrzej Kochel、Zbigniew Galewski

  DOI：10.1016/j.molliq.2016.11.014

  日期：2017.1

  This paper presents results of our studies of a full homologous series of 4-(4′-alkyloxyphenylazo)benzoyl chlorides. Until now these compounds have been used only as intermediates for more complex materials and their properties were not investigated as acid chlorides are considered unstable and hence useless for applications. We show that they are in fact quite durable and possess liquid-crystalline

  本文介绍了我们对4-（4'-烷氧基苯基偶氮）苯甲酰氯的完全同源系列的研究结果。迄今为止，这些化合物仅用作更复杂材料的中间体，尚未研究其性能，因为酰基氯被认为是不稳定的，因此在应用中无用。我们证明它们实际上很耐久，并在很宽的温度范围内具有液晶性能。此外，该系列还证明了顺式-反式异构化的快速切换时间少于一个小时的弛豫时间，这使得这些化合物有望成为光学切换的材料。