4-[4-[(4-cyanophenyl)azo]phenoxy]butyric acid | 185986-06-5

• 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-[4-[(4-cyanophenyl)azo]phenoxy]butyric acid
• 英文别名: 4-[4-(4-Cyanophenylazo)phenoxy]-butanoic acid；4-[4-[(4-cyanophenyl)diazenyl]phenoxy]butanoic acid
• CAS: 185986-06-5
• 化学式: C₁₇H₁₅N₃O₃
• 分子量: 309.324
• InChiKey: BEIALWKLVZDXMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  95
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[4-[(4-cyanophenyl)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-cyanophenyl)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：

  4-[4-[(4-cyanophenyl)azo]phenoxy]butyric acid ethyl ester 在 水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 以74%的产率得到4-[4-[(4-cyanophenyl)azo]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

• Physically functional materials
  申请人：Riso National Laboratory

  公开号：US06376655B1

  公开（公告）日：2002-04-23

  The invention relates to novel monodisperse or polydisperse compounds, in general named DNO (diamino acid N&agr;-substituted oligopeptides), preferably low molecular weight polypeptides, e.g., based on ornithine, lysine, diaminobutyric acid, diaminopropionic acid, aminoethylglycine or other amino acids or peptides having azobenzenes or other physicially functional groups, e.g., photoresponsive groups, as side chains. These compounds may be synthesized using solid phase peptide synthesis techniques. Materials, e.g., thin films, comprising such compounds may be used for optical storage of information (holographic data storage), nonlinear optics (NLO), as photoconductors, photonic band-gap materials, electrically conducting materials, electroluminescent materials, piezo-electric materials, pyroelectric materials, magnetic materials, ferromagnetic materials, ferroelectric materials, photorefractive materials, or materials in which light-induced conformational changes can be produced. Optical anisotropy may reversibly be generated with polarized laser light whereby a hologram is formed. First order diffraction efficiencies of up to around 80% have been obtained.

  本发明涉及新型单分散或多分散化合物，通常称为DNO（N&agr;-取代二氨基酸寡肽），优选低分子量多肽，例如基于鸟氨酸、赖氨酸、二氨基丁酸、二氨基丙酸、氨基乙基甘氨酸或其他具有偶氮苯或其他物理功能基团（例如光响应基团）的氨基酸或肽。这些化合物可以使用固相肽合成技术合成。包括这些化合物的材料，例如薄膜，可用于光学信息存储（全息数据存储）、非线性光学（NLO）、作为光电导体、光子带隙材料、电导材料、电致发光材料、压电材料、热释电材料、磁性材料、铁磁材料、铁电材料、光折变材料或可以产生光诱导构象变化的材料。通过极化激光光束可逆地产生光学各向异性，从而形成全息图。一阶衍射效率可高达约80%。
• 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.