4-[4-[(4-methoxyphenyl)azo]phenoxy]butyric acid | 1204522-67-7

• 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: 4-[4-[(4-methoxyphenyl)azo]phenoxy]butyric acid
• 英文别名: 4-[4-[(4-Methoxyphenyl)diazenyl]phenoxy]butanoic acid；4-[4-[(4-methoxyphenyl)diazenyl]phenoxy]butanoic acid
• CAS: 1204522-67-7
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: KPUADURDZNQEIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  4-[4-[(4-methoxyphenyl)azo]phenoxy]butyric 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4-[4-[(4-methoxyphenyl)azo]phenoxy]butyryl 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：

  苯酚 在 盐酸 、 potassium carbonate 、 potassium hydroxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 生成 4-[4-[(4-methoxyphenyl)azo]phenoxy]butyric acid
  参考文献：
  名称：

  Cellulose-Based Liquid Crystalline Photoresponsive Films with Tunable Surface Wettability

  摘要：

  We report on a new type of liquid crystalline cellulosic films with light controllable reversible wettability. The films are prepared from a thermotropic cellulose derivative functionalized with azo-containing groups. These groups exhibit dynamic changes in interfacial properties in response to UV irradiation. The UV irradiation induces trans-to-cis isomerization in the azobenzene moiety, which causes a conformational change in the upper molecular layers of the thin films. These changes originate a hydrophobic to comparatively hydrophilic transformation of the surface. The reversible wettability of the surface results from the cis/trans photo and thermal isomerization. The UV-vis absorption spectra, as well as contact angle measurements with UV irradiation, clearly support the understanding of the phenomenon. This type of surface design enables the amplification of molecular level conformational transitions to macroscopic changes in interface properties using the means of isomerism This opens new opportunities in surface engineering using eco-friendly cellulose manipulation.

  DOI：

  10.1021/la200422q

文献信息

• Fluorescent nanoparticles assembled from a poly(ionic liquid) for selective sensing of copper ions
  作者：Kun Cui、Xuemin Lu、Wei Cui、Jun Wu、Xumeng Chen、Qinghua Lu

  DOI：10.1039/c0cc03900d

  日期：——

  Fluorescent nanoparticles were formed from a poly(ionic liquid) through ion interactions. The fluorescent nanoparticles show highly fluorescent intensity and stability to UV light irradiation and were utilized for highly sensitive and selectivity fluorescent sensor of copper ion.

  荧光纳米粒子是通过离子相互作用由聚（离子液体）形成的。该荧光纳米粒子表现出高荧光强度和对紫外光照射的稳定性，可用于铜离子的高灵敏度和选择性荧光传感器。
• 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.
• Cellulose-Based Liquid Crystalline Photoresponsive Films with Tunable Surface Wettability
  作者：L. F. V. Pinto、S. Kundu、P. Brogueira、C. Cruz、S. N. Fernandes、A. Aluculesei、M. H. Godinho

  DOI：10.1021/la200422q

  日期：2011.5.17

  We report on a new type of liquid crystalline cellulosic films with light controllable reversible wettability. The films are prepared from a thermotropic cellulose derivative functionalized with azo-containing groups. These groups exhibit dynamic changes in interfacial properties in response to UV irradiation. The UV irradiation induces trans-to-cis isomerization in the azobenzene moiety, which causes a conformational change in the upper molecular layers of the thin films. These changes originate a hydrophobic to comparatively hydrophilic transformation of the surface. The reversible wettability of the surface results from the cis/trans photo and thermal isomerization. The UV-vis absorption spectra, as well as contact angle measurements with UV irradiation, clearly support the understanding of the phenomenon. This type of surface design enables the amplification of molecular level conformational transitions to macroscopic changes in interface properties using the means of isomerism This opens new opportunities in surface engineering using eco-friendly cellulose manipulation.