4-[(4-phenylazo)phenoxy]butyric acid | 147022-80-8

• 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-phenylazo)phenoxy]butyric acid
• 英文别名: 4-(4-Phenyldiazenylphenoxy)butanoic acid
• CAS: 147022-80-8
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: QSEQLMGFHMUIMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  4-[(4-phenylazo)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-phenylazo)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：

  4-[(4-phenylazo)phenoxy]butyric acid ethyl ester 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以90%的产率得到4-[(4-phenylazo)phenoxy]butyric acid
  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

文献信息

• Disulphide Cross‐Linked Ultrashort Peptide Hydrogelator for Water Remediation
  作者：Basab Kanti Das、Raju Samanta、Sahnawaz Ahmed、Bapan Pramanik

  DOI：10.1002/chem.202300312

  日期：2023.7.3

  A cysteine-containing ultrashort peptide hydrogelator undergoes disulphide bond formation and forms a self-supporting, thixotropic, insoluble hydrogel via both covalent and non-covalent interactions. The resultant hydrogelator was exploited to remove toxic organic dyes from contaminated water in the gel phase and solid supports, indicating its potential applicability for water remediation.

  含半胱氨酸的超短肽水凝胶剂经历二硫键形成，并通过共价和非共价相互作用形成自支撑、触变、不溶性水凝胶。所得水凝胶剂被用来去除凝胶相和固体载体中污染水中的有毒有机染料，表明其在水体修复方面的潜在适用性。
• 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.