(E)-4-(p-tolyldiazenyl)phenol | 79349-38-5

• 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: (E)-4-(p-tolyldiazenyl)phenol
• 英文别名: 4-[(4-methylphenyl)azo]phenol；4-hydroxy-4'-methylazobenzene
• CAS: 79349-38-5
• 化学式: C₁₃H₁₂N₂O
• 分子量: 212.251
• InChiKey: PLPWYNVDCPPLMM-CCEZHUSRSA-N

物化性质

• 熔点：
  154-155 °C(Solv: acetic acid (64-19-7))
• 沸点：
  384.3±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.95
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-4-(p-tolyldiazenyl)phenol 在 sodium azide 、 18-冠醚-6 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (E)-2-(4-(p-tolyldiazenyl)phenoxy)ethanamine
  参考文献：
  名称：

  Synthesis of photoresponsive hybrid alginate hydrogel with photo-controlled release behavior

  摘要：

  A photoresponsive hybrid alginate hydrogel was successfully prepared by Ca2+-mediated crosslinking reaction with a mixture of beta-cyclodextrin-grafted alginate (beta-CD-Alg) and diazobenzene-modified poly(ethylene glycol) (Az(2)-PEG). The water-soluble Az(2)-PEG exhibits efficient trans-to-cis isomerization of the terminal azobenzene moieties under UV-light irradiation and readily switched back to the initial trans state under visible light. Because of low affinity between beta-CD and cis-Az, the host-guest inclusion complex formed by beta-CD and trans-Az gradually dissociates under UV-light exposure. Accordingly, the bulk gel exhibits substantial photo-induced transformation in gel morphology by the appearance of significant comb-like cavities. This photosensitive behavior accompanied by the structural degradation enables the rapid release of entrapped dye molecules under UV light stimulus. Moreover, an incident light with higher power and mild acidic environment are capable of accelerating the photo-triggered release, thus allowing the potential applications toward acute wound healing. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2014.11.043
• 作为产物：
  描述：

  乙烷,三氯氟- 在 盐酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (E)-4-(p-tolyldiazenyl)phenol
  参考文献：
  名称：

  降冰片二烯：用于高分子量聚合物级联“点击”偶联的坚固且可扩展的构件

  摘要：

  在此，我们报告了基于降冰片二烯 (NBD) 的可扩展且合成稳健的构建块的开发，该构建块可以使用传统的活性聚合技术广泛地结合到各种大分子结构中。通过利用四嗪的选择性和快速脱保护，可以以定量和有效的方式将高反应性的“掩蔽”环戊二烯 (Cp) 官能团作为链端基团引入合成聚合物中。该平台的正交性进一步实现了级联点击过程，其中“未掩蔽”的 Cp 可以通过传统的 Diels-Alder 反应与亲二烯体（如马来酰亚胺）快速反应。

  DOI：

  10.1021/jacs.9b06328

文献信息

• 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。
• The selective synthesis of <i>N</i>-arylbenzene-1,2-diamines or 1-arylbenzimidazoles by irradiating 4-methoxy-4′-substituted-azobenzenes in different solvents
  作者：Po-Yi Chen、Chi-Wei Hsu、Tong-Ing Ho、Jinn-Hsuan Ho

  DOI：10.1039/d0ra10068d

  日期：——

  The solvent-controllable photoreaction of 4-methoxyazobenzenes to afford 1-aryl-1H-benzimidazoles or N-arylbenzene-1,2-diamines has been studied. The irradiation of 4-methoxyazobenzenes in DMF containing 0.5 M hydrochloric acid provided N 2-aryl-4-methoxybenzene-1,2-diamines as the major product, while irradiation in acetal containing 0.16 M hydrochloric acid led to 1-aryl-6-methoxy-2-methyl-1H-benzimidazoles

  研究了 4-甲氧基偶氮苯的溶剂可控光反应得到 1-芳基-1H-苯并咪唑或 N-芳基苯-1,2-二胺。4-甲氧基偶氮苯在含有 0.5 M 盐酸的 DMF 中辐照产生 N 2-aryl-4-methoxybenzo-1,2-diamines 作为主要产物，而在含有 0.16 M 盐酸的乙缩醛中辐照产生 1-aryl-6-主要产品为甲氧基-2-甲基-1H-苯并咪唑。还讨论了解释选择性的可能反应机制。
• PHOTORESPONSIVE MATERIAL, ADHESIVE, OPTICAL SWITCHING MATERIAL, TONER, AND IMAGE FORMING METHOD
  申请人：Konica Minolta, Inc.

  公开号：US20210332272A1

  公开（公告）日：2021-10-28

  A composition includes an isomerized polymer containing a structural unit containing an isomerized structure and an isomerized low molecular weight compound, the composition being fluidized by light irradiation from a solid state and being reversibly non-fluidized.

  一种组合物包括含有异构化结构单元和异构化低分子量化合物的异构化聚合物，该组合物通过固态光照而变为流动状态，并可可逆地变为非流动状态。
• Receptor with an Active Methylene Group as Binding Site for Extraction of Inorganic Fluoride Ions from Seawater
  作者：Madhuprasad、Darshak R. Trivedi

  DOI：10.1002/cplu.201402018

  日期：2014.7

  deprotonation of the methylene proton, which has been confirmed by 1H NMR titration. The receptors were evaluated for real‐life applicability by extracting F− ions from aqueous media and seawater into organic media. Receptor R2 was able to extract F− ions from seawater with 99 % efficiency. The level of F− ions present in seawater has been quantified and found to be 1.4 ppm, which is comparable to the reported

  两个新的受体 R1和R2基于与活性亚甲基如结合位点三苯基鏻盐已经被设计和用于检测的F合成-离子。发现这些受体在有机介质中的检出限为0.2 ppm。在添加˚F -离子，Δ λ最大观察到受体的188纳米和256纳米的 R1和R2分别。检测过程之后是亚甲基质子的去质子化，这已通过1 H NMR滴定证实。该受体是通过提取F代表现实生活中的适用性评价-离子从水介质和海水进入有机介质。受体 R2是能够提取物F -从海水以99％的效率的离子。F的电平-在海水中存在的离子已被量化，结果为1.4 ppm的，这与文献报道值。
• Photo-responsive high-molecular compound, photo-responsive high-molecular composition, dicarboxylic acid monomer, polyester, optical recording medium and optical record reproducing device
  申请人：FUJI XEROX CO., LTD.

  公开号：US20040029038A1

  公开（公告）日：2004-02-12

  In the present invention, a photosensitive layer of an optical recording medium includes a photo-responsive high-molecular compound comprising a photo-responsive group (e.g., an azobenzene derivative) which is geometrically isomerized by light radiation, and a liquid crystal linear mesogen group (e.g., a biphenyl derivative), wherein the photo-responsive group and the linear mesogen group are respectively bonded as side chains. The invention provides an optical recording medium enabling large scale recording by making the photosensitive layer thick without impairing recording characteristics. The photo-responsive high-molecular compound preferably comprises an aromatic ring on a main chain. Further, the photo-responsive high-molecular compound preferably comprises a structural unit which is capable of forming a liquid-crystalline or crystalline polymer and a structural unit which is capable of forming an amorphous polymer.

  在本发明中，光学记录介质的光敏层包括一种光响应高分子化合物，其中包括一种光响应基团（例如偶氮苯衍生物），该基团通过光辐射几何异构化，以及一种液晶线性介质基团（例如联苯衍生物），其中光响应基团和线性介质基团分别作为侧链键合。本发明提供了一种光学记录介质，使光敏层变厚而不影响记录特性，从而实现大规模记录。光响应高分子化合物最好包括主链上的芳香环。此外，光响应高分子化合物最好包括能够形成液晶或结晶聚合物的结构单元和能够形成非晶聚合物的结构单元。