4-bromo-2-methyl-4'-(6-hydroxyhexyloxy)azobenzene | 784189-20-4

• 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-bromo-2-methyl-4'-(6-hydroxyhexyloxy)azobenzene
• CAS: 784189-20-4
• 化学式: C₁₉H₂₃BrN₂O₂
• 分子量: 391.308
• InChiKey: BTHQDGIXLCUYEY-QURGRASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  54.18
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-bromo-2-methyl-4'-(6-hydroxyhexyloxy)azobenzene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide sodium hydroxide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 11.0h， 生成 4'-ethynyl-2'-methyl-4-(6-hydroxyhexyloxy)azobenzene
  参考文献：
  名称：

  Azotolane Liquid-Crystalline Polymers:  Huge Change in Birefringence by Photoinduced Alignment Change

  摘要：

  Novel liquid-crystalline polymers (LCPs) containing a long azotolane moiety were synthesized, and the relationship between the chemical structures and the photoresponsive behavior was investigated. All homogeneously aligned LCP films exhibited extremely high values of birefringence (Deltan) in the wide wavelength range. Specifically, the azotolane LCP with two azobenzene units showed the most efficient change in the alignment of the azotolane moiety with a huge change in Deltan (>/=0.65). This means that the high value of Deltan in the homogeneously aligned state can be converted to the change in Deltan effectively.

  DOI：

  10.1021/ja0664382
• 作为产物：
  描述：

  2-甲基-4-溴苯胺 在 sodium nitrate 、 tetrafluoroboric acid 、 potassium carbonate 作用下， 生成 4-bromo-2-methyl-4'-(6-hydroxyhexyloxy)azobenzene
  参考文献：
  名称：

  Highly birefringent liquid-crystalline polymers for photonic applications: synthesis of liquid-crystalline polymers with side-chain azo-tolane mesogens and their holographic properties

  摘要：

  我们合成了高双折射液晶聚合物 (LCP)，其中含有一个直接连接到甲苯分子的偶氮苯基 (P3ATm)，烷基间隔长度 (CH2)m 变化为 m = 6、9 和 12。所有 LCP 在较宽的温度范围内（>170 °C）都呈现出向列相。均匀配向的 LCP 薄膜显示出较高的双折射值（约 0.4），光诱导配向变化可引起双折射的大幅变化。在玻璃态中探索了 LCP 的光栅形成。当干涉图案的亮区完成有序-无序变化时，衍射效率（η）达到最大值。对光强对光栅形成影响的研究表明，即使偶氮-甲苯分子的排列变化很小，衍射效率也很高（η = 20%）。此外，研究还发现光栅形成的行为取决于 P3ATm 的烷基间隔长度。

  DOI：

  10.1039/b506131h

文献信息

• Synthesis and Photoresponsive Behavior of a Liquid-Crystalline Polymer with a 4-Ring Azotolane Moiety with Huge Birefringence
  作者：Kunihiko Okano、Atsushi Shishido、Tomiki Ikeda

  DOI：10.1080/15421400701680911

  日期：2007.12.14
• Azotolane Liquid-Crystalline Polymers:  Huge Change in Birefringence by Photoinduced Alignment Change
  作者：Kunihiko Okano、Osamu Tsutsumi、Atsushi Shishido、Tomiki Ikeda

  DOI：10.1021/ja0664382

  日期：2006.12.1

  Novel liquid-crystalline polymers (LCPs) containing a long azotolane moiety were synthesized, and the relationship between the chemical structures and the photoresponsive behavior was investigated. All homogeneously aligned LCP films exhibited extremely high values of birefringence (Deltan) in the wide wavelength range. Specifically, the azotolane LCP with two azobenzene units showed the most efficient change in the alignment of the azotolane moiety with a huge change in Deltan (>/=0.65). This means that the high value of Deltan in the homogeneously aligned state can be converted to the change in Deltan effectively.
• Highly birefringent liquid-crystalline polymers for photonic applications: synthesis of liquid-crystalline polymers with side-chain azo-tolane mesogens and their holographic properties
  作者：Kunihiko Okano、Atsushi Shishido、Osamu Tsutsumi、Takeshi Shiono、Tomiki Ikeda

  DOI：10.1039/b506131h

  日期：——

  We have synthesized highly birefringent liquid-crystalline polymers (LCPs) containing an azobenzene group directly connected to a tolane moiety (P3ATm), in which the alkyl spacer length (CH2)m was varied as m = 6, 9 and 12. All LCPs showed a nematic phase in a broad temperature range (>170 °C). The homogeneously aligned LCP films showed a high value of birefringence (about 0.4) and a large change in the birefringence could be induced by photoinduced alignment change. Grating formation of LCPs has been explored in a glassy state. The diffraction efficiency (η) showed a maximum when an order–disorder change was completed in the bright areas of the interference patterns. Studies on the effects of light intensity on the grating formation suggested that the diffraction efficiency was high (η = 20%) even though the alignment change of the azo-tolane moieties was small. Furthermore, the behavior of the grating formation was found to be dependent on the alkyl spacer length of P3ATm.

  我们合成了高双折射液晶聚合物 (LCP)，其中含有一个直接连接到甲苯分子的偶氮苯基 (P3ATm)，烷基间隔长度 (CH2)m 变化为 m = 6、9 和 12。所有 LCP 在较宽的温度范围内（>170 °C）都呈现出向列相。均匀配向的 LCP 薄膜显示出较高的双折射值（约 0.4），光诱导配向变化可引起双折射的大幅变化。在玻璃态中探索了 LCP 的光栅形成。当干涉图案的亮区完成有序-无序变化时，衍射效率（η）达到最大值。对光强对光栅形成影响的研究表明，即使偶氮-甲苯分子的排列变化很小，衍射效率也很高（η = 20%）。此外，研究还发现光栅形成的行为取决于 P3ATm 的烷基间隔长度。