3,5-dimethyl-4-(4-cyanophenylazo)aniline | 478946-09-7

• 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: 3,5-dimethyl-4-(4-cyanophenylazo)aniline
• 英文别名: 4-[(4-Amino-2,6-dimethylphenyl)diazenyl]benzonitrile；4-[(4-amino-2,6-dimethylphenyl)diazenyl]benzonitrile
• CAS: 478946-09-7
• 化学式: C₁₅H₁₄N₄
• 分子量: 250.303
• InChiKey: XCWKGKBYBYKZSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二苯并-24-冠醚-8 、 、 3,5-dimethyl-4-(4-cyanophenylazo)aniline 生成 C₃₂H₃₁N₅*F₆P^(1-)*C₂₄H₃₂O₈*H⁽¹⁺⁾
  参考文献：
  名称：

  一对[2]轮烷的五态分子穿梭：响应酸和碱刺激的不同输出。

  摘要：

  在这项研究中，我们合成了两种酸/碱可控制的[2]轮烷，分别以氨基重氮苯和氨基香豆素单元为生色团，分别以二苯并[24] crown-8和二苯并[25] crown-8单元为大环组分。 。每个[2]轮烷含有N-烷基芳基胺（铵）和N，N-二烷基胺（铵）以其冠醚成分的结合位点为中心。发色团的吸收方式取决于所包围的大环组分的位置和质子化的程度，每种[2]轮烷都有明显的三种不同状态（在酸性，中性和碱性条件下）。混合的[2]轮烷化合物体系根据添加的酸或碱的量和强度，根据氨基的质子化程度显示出逐步和独立的分子穿梭行为。这样，该系统提供了五个不同的吸收信号作为输出，可以使用UV / Vis光谱法读取该信号。

  DOI：

  10.1002/asia.201600743
• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 、 对氨基苯腈 在 硫酸 、 sodium nitrite 、 甲酸 、 sodium acetate 作用下， 以 水 、 溶剂黄146 、 丙酸 为溶剂， 反应 4.08h， 以88%的产率得到3,5-dimethyl-4-(4-cyanophenylazo)aniline
  参考文献：
  名称：

  Epoxy-based polymers functionalized with bisazo chromophores: Synthesis, characterization and photoresponsive behavior

  摘要：

  In this work, two series of epoxy-based polymers bearing bisazo chromophores were synthesized from two precursor polymers (BP-AN and BP35-AN) through post-polymerization azo-coupling reactions. The polymers were prepared to contain bisazo chromophores with different electron-withdrawing groups and different numbers of methyl substituents, which were characterized by (1)H NMR, FT-IR, GPC, UV-vis, and thermal analysis. The photoinduced birefringence and surface-relief-grating (SRG) formation of the polymers were studied by irradiating spin-coated films of the polymers with laser light at three different wavelengths (488, 532, and 589 nm). The results show that the polymers containing bisazo chromophores possess broader and red-shifted absorption bands compared with ordinary azobenzene-containing polymers. The electron-withdrawing groups on the bisazo chromophores show significant effect on the absorption band positions. The behavior of photoinduced birefringence and surface-relief-grating (SRG) formation is closely correlated with the chromophore structures and excitation wavelength of the laser light. Both electron-withdrawing groups and methyl substituents on the bisazo chromophores show obvious influences on the photoinduced birefringence growth rate and SRG formation rate. The proper methyl substitution on the bisazo chromophores shows ability to enhance the photoinduced birefringence growth rate, birefringence saturation level, and SRG formation rate. The bisazo polymers obtained in this study can be further explored for applications in telecommunication, data-storage, sensors, and other optical devices. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.05.040

文献信息

• Epoxy-based polymers functionalized with bisazo chromophores: Synthesis, characterization and photoresponsive behavior
  作者：Xiaolin Wang、Jianjun Yin、Xiaogong Wang

  DOI：10.1016/j.polymer.2011.05.040

  日期：2011.7

  In this work, two series of epoxy-based polymers bearing bisazo chromophores were synthesized from two precursor polymers (BP-AN and BP35-AN) through post-polymerization azo-coupling reactions. The polymers were prepared to contain bisazo chromophores with different electron-withdrawing groups and different numbers of methyl substituents, which were characterized by (1)H NMR, FT-IR, GPC, UV-vis, and thermal analysis. The photoinduced birefringence and surface-relief-grating (SRG) formation of the polymers were studied by irradiating spin-coated films of the polymers with laser light at three different wavelengths (488, 532, and 589 nm). The results show that the polymers containing bisazo chromophores possess broader and red-shifted absorption bands compared with ordinary azobenzene-containing polymers. The electron-withdrawing groups on the bisazo chromophores show significant effect on the absorption band positions. The behavior of photoinduced birefringence and surface-relief-grating (SRG) formation is closely correlated with the chromophore structures and excitation wavelength of the laser light. Both electron-withdrawing groups and methyl substituents on the bisazo chromophores show obvious influences on the photoinduced birefringence growth rate and SRG formation rate. The proper methyl substitution on the bisazo chromophores shows ability to enhance the photoinduced birefringence growth rate, birefringence saturation level, and SRG formation rate. The bisazo polymers obtained in this study can be further explored for applications in telecommunication, data-storage, sensors, and other optical devices. (C) 2011 Elsevier Ltd. All rights reserved.
• Five-State Molecular Shuttling of a Pair of [2]Rotaxanes: Distinct Outputs in Response to Acid and Base Stimuli
  作者：Masahiro Ueda、Shoya Terazawa、Yasuaki Deguchi、Masaki Kimura、Naoki Matsubara、Shinobu Miyagawa、Tsuneomi Kawasaki、Yuji Tokunaga

  DOI：10.1002/asia.201600743

  日期：2016.8.19

  dependent on the position of the encircling macrocyclic component and the degree of protonation, with three distinct states (under acidic, neutral, and basic conditions) evident for each [2]rotaxane. The mixed [2]rotaxane system displayed stepwise and independent molecular shuttling behavior based on the degree of protonation of the amino groups in response to both the amount and strength of added acids

  在这项研究中，我们合成了两种酸/碱可控制的[2]轮烷，分别以氨基重氮苯和氨基香豆素单元为生色团，分别以二苯并[24] crown-8和二苯并[25] crown-8单元为大环组分。 。每个[2]轮烷含有N-烷基芳基胺（铵）和N，N-二烷基胺（铵）以其冠醚成分的结合位点为中心。发色团的吸收方式取决于所包围的大环组分的位置和质子化的程度，每种[2]轮烷都有明显的三种不同状态（在酸性，中性和碱性条件下）。混合的[2]轮烷化合物体系根据添加的酸或碱的量和强度，根据氨基的质子化程度显示出逐步和独立的分子穿梭行为。这样，该系统提供了五个不同的吸收信号作为输出，可以使用UV / Vis光谱法读取该信号。