4-{2-[4-(hex-5-enyloxy)phenyl]diazenyl}benzoic acid | 156292-04-5

• 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-{2-[4-(hex-5-enyloxy)phenyl]diazenyl}benzoic acid
• 英文别名: 4-[(4-Hex-5-enoxyphenyl)diazenyl]benzoic acid；4-[(4-hex-5-enoxyphenyl)diazenyl]benzoic acid
• CAS: 156292-04-5
• 化学式: C₁₉H₂₀N₂O₃
• 分子量: 324.379
• InChiKey: BVBKISCQQLQNJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  五氟苯酚 、 4-{2-[4-(hex-5-enyloxy)phenyl]diazenyl}benzoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以40%的产率得到2,3,4,5,6-pentaflourophenyl 4-{[4-(hex-5-en-1-yloxy)phenyl]diazenyl}benzoate
  参考文献：
  名称：

  Synthesis and characterization of liquid crystalline azobenzene chromophores with fluorobenzene terminal

  摘要：

  Two series of fluorine-substituted benzoate ester type rod-shaped liquid crystals incorporating the azobenzene as side arm linked with terminal double bonds as polymerizable functional groups were synthesized and characterized by polarized-light optical microscopy (POM), differential scanning calorimetry (DSC) and UV-visible spectroscopy investigations. Thus, rod-shaped monomers, namely 4a and 4b having odd and even number of carbon in the terminal group exhibited nematic phase and SmA type phase was found at lower temperature. Compound 5 showed nematic phase whereas compound 6 showed SmA phase. These rod-shaped molecules exhibit strong photoisomerization behaviour in solution. The photoswitching properties of the compounds showed trans to cis isomerization in about 10 s, whereas the reverse process takes place about 120 min in solutions. Proposed materials may have potential to use it in optical storage devices. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.10.004
• 作为产物：
  描述：

  4-(4-羟基-偶氮苯)苯甲酸乙酯 在 水 、 potassium carbonate 、 potassium iodide 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 28.0h， 生成 4-{2-[4-(hex-5-enyloxy)phenyl]diazenyl}benzoic acid
  参考文献：
  名称：

  New pyrimidine-based photo-switchable bent-core liquid crystals

  摘要：

  我们合成并表征了首例液晶嘧啶基光开关弯曲核单体，这些单体以偶氮苯为侧臂，以末端双键为可聚合官能团。偏光光学显微镜（POM）、差示扫描量热仪（DSC）和 X 射线衍射分析表明，弯曲形状较低的同族化合物为结晶性质，而较高的同族化合物则显示出稳定的对映体 B6 相。它们在溶液中表现出快速的光异构化效应，而在液晶池中则表现出相对缓慢的光异构化效应。在溶液中，反式-顺式和顺式-反式分别在 3 秒和 200 秒左右发生，而在固体中，则在 10 秒到 200 分钟左右发生。这是偶氮苯液晶在溶液中表现出极快切换特性的首例。

  DOI：

  10.1039/c3nj00359k

文献信息

• Synthesis and characterization of liquid crystalline azobenzene chromophores with fluorobenzene terminal
  作者：Md Lutfor Rahman、Gurumurthy Hegde、Mahrokh Azazpour、Mashitah Mohd Yusoff、Sandeep Kumar

  DOI：10.1016/j.jfluchem.2013.10.004

  日期：2013.12

  Two series of fluorine-substituted benzoate ester type rod-shaped liquid crystals incorporating the azobenzene as side arm linked with terminal double bonds as polymerizable functional groups were synthesized and characterized by polarized-light optical microscopy (POM), differential scanning calorimetry (DSC) and UV-visible spectroscopy investigations. Thus, rod-shaped monomers, namely 4a and 4b having odd and even number of carbon in the terminal group exhibited nematic phase and SmA type phase was found at lower temperature. Compound 5 showed nematic phase whereas compound 6 showed SmA phase. These rod-shaped molecules exhibit strong photoisomerization behaviour in solution. The photoswitching properties of the compounds showed trans to cis isomerization in about 10 s, whereas the reverse process takes place about 120 min in solutions. Proposed materials may have potential to use it in optical storage devices. (C) 2013 Elsevier B.V. All rights reserved.
• New pyrimidine-based photo-switchable bent-core liquid crystals
  作者：Md Lutfor Rahman、Gurumurthy Hegde、Mashitah Mohd Yusoff、Muhammad Nor Fazli A. Malek、Hosapalya T. Srinivasa、Sandeep Kumar

  DOI：10.1039/c3nj00359k

  日期：——

  The first examples of liquid crystalline pyrimidine-based photo-switchable bent-core monomers incorporating azobenzene as side arms linked with terminal double bonds as polymerizable functional groups are synthesized and characterized. Polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction analysis reveal that the bent-shaped lower homologue compounds are crystalline in nature whereas higher homologue compounds display the stable enantiotropic B6 phase. They exhibit fast photoisomerization effects in solution and relatively slow photoisomerization effects in liquid crystal cells. In solution both trans–cis and cis–trans occur at around 3 s and 200 s, respectively, whereas in solids they occur at around 10 s to 200 min. These are some of the first examples of azobenzene liquid crystals which exhibit very fast switching properties in solutions.

  我们合成并表征了首例液晶嘧啶基光开关弯曲核单体，这些单体以偶氮苯为侧臂，以末端双键为可聚合官能团。偏光光学显微镜（POM）、差示扫描量热仪（DSC）和 X 射线衍射分析表明，弯曲形状较低的同族化合物为结晶性质，而较高的同族化合物则显示出稳定的对映体 B6 相。它们在溶液中表现出快速的光异构化效应，而在液晶池中则表现出相对缓慢的光异构化效应。在溶液中，反式-顺式和顺式-反式分别在 3 秒和 200 秒左右发生，而在固体中，则在 10 秒到 200 分钟左右发生。这是偶氮苯液晶在溶液中表现出极快切换特性的首例。