4-[(4-羟基苯基)偶氮]苯甲腈 | 107016-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 中文名称: 4-[(4-羟基苯基)偶氮]苯甲腈
• 英文名称: 4-[(4-hydroxyphenyl)azo]benzonitrile
• 英文别名: 4-<(E)-2-(4-hydroxyphenyl)-1-diazenyl>benzonitrile；(E)-4-((4-hydroxyphenyl)diazenyl)benzonitrile；4-[(E)-(4-hydroxyphenyl)diazenyl]benzonitrile；4-<(4'-cyanophenyl)azo>phenol；4'-cyano-4-hydroxyazobenzene；4-cyano-4'-hydroxyazobenzene；4-hydroxy-4'-cyanoazobenzene
• CAS: 107016-88-6
• 化学式: C₁₃H₉N₃O
• 分子量: 223.234
• InChiKey: HKRIZVYPOGYCLC-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.74
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[(4-羟基苯基)偶氮]苯甲腈 在 lithium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 N-Ac-L-trans-Pro(4-<4-<(E)-2-(4-cyanophenyl)-1-diazenyl>phenoxy>)-OH
  参考文献：
  名称：

  A Remarkably Efficient Azobenzene Peptide for Holographic Information Storage

  摘要：

  A new family of proline-based azobenzene peptides (DNO) for holographic information storage is reported.:By use of polarization holography, it was found that gratings with extraordinarily high diffraction efficiency (up to 80%) can be recorded in hundreds of milliseconds in a similar to 13-mu m-thick film of dimer 10. This represents a decrease of the response time by more than 2 orders of magnitude when compared to that of the ornithine-based DNO dimer previously reported. Furthermore, it supports the expectation that increasing the rigidity of the peptide backbone is: crucial in the design of effective azobenzene peptides for optical recording. Gratings recorded in 10 can be erased-by circularly polarized light in a few-seconds. It is also noted that, unlike DNOs previously reported, 10 is soluble in common organic solvents and can be assembled by solution phase synthesis, which is mandatory for large-scale fabrication.

  DOI：

  10.1021/ja981402y
• 作为产物：
  描述：

  在 cobalt(II) nitrate 作用下， 以 水 为溶剂， 反应 0.17h， 生成 4-[(4-羟基苯基)偶氮]苯甲腈
  参考文献：
  名称：

  为激活体积顺至-反式azophenols的异构化反应：清晰的机械指标？†

  摘要：

  热顺式-到-反式的一系列羟基取代的偶氮衍生物的异构化反应，以研究在控制异构化机构，该溶剂中的可能作用的研究Kinetico公司-机理上作为温度和压力的函数即 反转与旋转。在不同温度和压力下进行的动力学实验的观测一阶速率常数的变化用于确定热激活参数ΔH ‡和ΔS ‡以及压力激活参数ΔV ‡。此外，还使用氘代物质或溶剂进行了一些实验。对于某些研究的系统，所报告的结果可以解释为指示从非极性溶剂的转化机理转变为能够氢键的极性溶剂的旋转机理的转变。但是，在所有研究的案例中，旋转机构的操作都可以更一致地说明所观察到的数据。

  DOI：

  10.1039/c7cp07349f

文献信息

• Monolayer and Bilayer Stability of Ammonium Amphiphiles Carrying an Azobenzene Unit – Effects of Substituents at the Azobenzene Unit
  作者：Marcel D. Everaars、Antonius T. M. Marcelis、Ernst J. R. Sudhölter

  DOI：10.1002/jlac.199719970106

  日期：1997.1

  double-chained ammonium amphiphiles carrying one azobenzene moiety (I) have been synthesized. The bilayer-stabilizing effect of different azobenzenes (ABs) has been investigated by measuring the “gel-to-liquid crystalline” phase transition temperatures of the formed bilayers in water using differential scanning calorimetry. It is found that the stabilizing effect of the azobenzenes strongly depends

  已经合成了带有一个偶氮苯部分（I）的新型双链铵两亲物。通过使用差示扫描量热法测量水中形成的双层的“凝胶到液晶”相变温度，已经研究了不同偶氮苯（ABs）的双层稳定作用。发现偶氮苯的稳定作用强烈地取决于芳环上的取代基。稳定效果按以下顺序增加：F
• Photo-driven optical oscillators in the kHz range based on push–pull hydroxyazopyridines
  作者：Jaume Garcia-Amorós、Santi Nonell、Dolores Velasco

  DOI：10.1039/c1cc10302d

  日期：——

  Push–pull azophenols are valuable target molecules for stable photo-driven optical oscillators. Hydroxyazopyridinium methyl iodide salts show oscillation frequencies up to 10 kHz with no signs of fatigue upon continuous work.

  推拉偶氮苯酚是稳定光驱动光振荡器的重要目标分子。羟基氮吡啶甲基碘盐的振荡频率高达 10 kHz，连续工作时不会出现疲劳迹象。
• Novel Phenyldiazenyl Fibrate Analogues as PPAR α/γ/δ Pan-Agonists for the Amelioration of Metabolic Syndrome
  作者：Letizia Giampietro、Antonio Laghezza、Carmen Cerchia、Rosalba Florio、Lucia Recinella、Fabio Capone、Alessandra Ammazzalorso、Isabella Bruno、Barbara De Filippis、Marialuigia Fantacuzzi、Claudio Ferrante、Cristina Maccallini、Paolo Tortorella、Fabio Verginelli、Luigi Brunetti、Alessandro Cama、Rosa Amoroso、Fulvio Loiodice、Antonio Lavecchia

  DOI：10.1021/acsmedchemlett.8b00574

  日期：2019.4.11

  The development of PPARα/γ dual or PPARα/γ/δ pan-agonists could represent an efficacious approach for a simultaneous pharmacological intervention on carbohydrate and lipid metabolism. Two series of new phenyldiazenyl fibrate derivatives of GL479, a previously reported PPARα/γ dual agonist, were synthesized and tested. Compound 12a was identified as a PPAR pan-agonist with moderate and balanced activity

  PPARα/γ双重或PPARα/γ/δ泛激动剂的发展可能代表一种同时进行药理干预碳水化合物和脂质代谢的有效方法。合成并测试了两个系列的新的GL479苯基二氮烯基贝特酸酯衍生物（先前报道的PPARα/γ双激动剂）。化合物12a被鉴定为对三种PPAR亚型（α，γ，δ）具有中等且平衡活性的PPAR泛激动剂。此外，对接实验表明，与PPARα或PPARδ相比，12a在PPARγ中采用不同的结合方式，为进一步的PPAR泛激动剂结构指导设计提供了结构基础。在体外均评估了12a的有益作用，关于PPAR靶向关键代谢基因的表达，以及离体在两种大鼠组织炎症模型中的作用。所获得的结果使得可以认为该化合物是开发新型PPAR泛激动剂的有趣线索，所述PPAR泛激动剂具有可用于代谢综合症治疗的活化特性。
• Effect of media polarity on the photoisomerisation of substituted stilbene, azobenzene and imine chromophores
  作者：N. R. King、Eric A. Whale、Fred J. Davis、Andrew Gilbert、Geoffrey R. Mitchell

  DOI：10.1039/a607980f

  日期：——

  The influence of substituents and media polarity on the photoinducedE→Z geometrical isomerisation of the stilbene, azobenzene and N-benzylideneaniline chromophores has been compared and assessed. The efficiency of the process in all three systems is markedly dependent on the presence and characteristics of electron-donor and electron-acceptor substituents at the 4- and 4′-positions. The results are discussed in terms of relaxation of the E-excited singlet state. In the absence of a nitro substituent, relaxation to the S 1 orthogonal state competes effectively with non-productive intramolecular electron transfer; in the presence of a nitro substituent, the T 1 orthogonal state is formed from inter-system crossing. For systems with a 4-nitro and a 4′-electron-donor substituent, access to the triplet state is inhibited by polar solvents promoting formation of the inactive charge-transfer state from the S 1 state, and no isomerisation is observed. Similar effects are observed in both solution and polymer films. Such variations in behaviour have important implications for the utilisation of the chromophores in nonlinear optical phenomena including photorefractivity.

  我们比较并评估了取代基和介质极性对二苯乙烯、偶氮苯和 N-亚苄基苯胺发色团的光诱导 E→Z 几何异构化的影响。在所有这三个系统中，该过程的效率明显取决于 4-和 4′-位置上电子供体和电子受体取代基的存在和特性。我们从 E 激发单态的弛豫角度对结果进行了讨论。在没有硝基取代基的情况下，向 S 1 正交态的弛豫与非生产性的分子内电子转移有效竞争；在有硝基取代基的情况下，T 1 正交态是由体系间的交叉形成的。对于具有 4-硝基和 4′-电子供体取代基的体系，极性溶剂会抑制三重态的进入，从而促进从 S 1 态形成非活性电荷转移态，并且不会观察到异构化现象。在溶液和聚合物薄膜中也观察到类似的效应。这种行为变化对利用发色团产生非线性光学现象（包括光折射）具有重要意义。
• Synthesis, characterization of azobenzene and cinnamate ester based calamitic liquid crystalline compounds and their photoresponsive properties
  作者：Chinnaiyan Selvarasu、Palaninathan Kannan

  DOI：10.1016/j.molstruc.2015.03.026

  日期：2015.7

  were synthesized and investigated its mesogenic and photochemical properties. Terminal substituents of the molecules were changed with various substituents like CN, Cl, H, CH 3 , and OCH 3 . Liquid crystalline properties of the synthesized compounds were studied and confirmed using differential scanning calorimetry, polarising optical microscopy. Compounds ( 4a – 4e ) exhibited a thermotropic mesomorph

  摘要 合成了一系列肉桂酸酯封端的含偶氮苯介晶，并研究了其介晶和光化学性质。分子的末端取代基被各种取代基如CN、Cl、H、CH 3 和OCH 3 改变。使用差示扫描量热法、偏光显微镜研究并证实合成化合物的液晶性质。化合物（4a - 4e）表现出热致介晶行为，即向列相和近晶相，这取决于末端取代基。热转变温度和中间相类型取决于末端取代基，随着共轭长度的增加，这些取代基归因于分子之间的内聚力增加。这些光致变色化合物在 330 和 340 nm 之间表现出很强的紫外可见吸收最大值。由于顺式构型，在选择性紫外光照射下产生反式-顺式异构化，在 450 nm 处产生新的最大值。