1,3,5-tris{[4-[4-[(4-methoxyphenyl)azo]phenoxy]butyryl]amino}benzene | 1204522-41-7

• 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: 1,3,5-tris{[4-[4-[(4-methoxyphenyl)azo]phenoxy]butyryl]amino}benzene
• 英文别名: N-[3,5-bis[4-[4-[(4-methoxyphenyl)diazenyl]phenoxy]butanoylamino]phenyl]-4-[4-[(4-methoxyphenyl)diazenyl]phenoxy]butanamide
• CAS: 1204522-41-7
• 化学式: C₅₇H₅₇N₉O₉
• 分子量: 1012.13
• InChiKey: YDRNQPMYNZTJGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  75
• 可旋转键数：
  27
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  217
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  4-[4-[(4-methoxyphenyl)azo]phenoxy]butyryl chloride 、 1,3,5-三氨基苯 在 三乙胺 、 lithium chloride 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以32%的产率得到1,3,5-tris{[4-[4-[(4-methoxyphenyl)azo]phenoxy]butyryl]amino}benzene
  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

• 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.