4-amino-2,6-dimethyl-4'-nitroazobenzene | 87317-14-4

• 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-amino-2,6-dimethyl-4'-nitroazobenzene
• 英文别名: 3,5-dimethyl-4-(4-nitrophenylazo)aniline；3,5-Dimethyl-4-[(4-nitrophenyl)diazenyl]aniline
• CAS: 87317-14-4
• 化学式: C₁₄H₁₄N₄O₂
• 分子量: 270.291
• InChiKey: JPXJUFVDKMXKAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  96.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-2,6-dimethyl-4'-nitroazobenzene 在 sodium sulfide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Design of a Highly Bistable Photoswitchable Tethered Ligand for Rapid and Sustained Manipulation of Neurotransmission

  摘要：

  Photoswitchable neurotransmitter receptors are powerful tools for precise manipulation of neural signaling. However, their applications for slow or long-lasting biological events are constrained by fast thermal relaxation of cis-azobenzene. We address this issue by modifying the ortho positions of azobenzene used in the tethered ligand. In cultured cells and intact brain tissue, conjugating inhibitory neurotransmitter receptors with one of the derivatives, dMPC1, allows bidirectional receptor control with 380 and 500 nm light. Moreover, the receptors can be locked in either an active or an inactive state in darkness after a brief pulse of light. This strategy thus enables both rapid and sustained manipulation of neurotransmission, allowing optogenetic interrogation of neural functions over a broad range of time scales.

  DOI：

  10.1021/jacs.8b03942
• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 、 4-硝基苯胺 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85%的产率得到4-amino-2,6-dimethyl-4'-nitroazobenzene
  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

• Design of a Highly Bistable Photoswitchable Tethered Ligand for Rapid and Sustained Manipulation of Neurotransmission
  作者：Wan-Chen Lin、Ming-Chi Tsai、Rajit Rajappa、Richard H. Kramer

  DOI：10.1021/jacs.8b03942

  日期：2018.6.20

  Photoswitchable neurotransmitter receptors are powerful tools for precise manipulation of neural signaling. However, their applications for slow or long-lasting biological events are constrained by fast thermal relaxation of cis-azobenzene. We address this issue by modifying the ortho positions of azobenzene used in the tethered ligand. In cultured cells and intact brain tissue, conjugating inhibitory neurotransmitter receptors with one of the derivatives, dMPC1, allows bidirectional receptor control with 380 and 500 nm light. Moreover, the receptors can be locked in either an active or an inactive state in darkness after a brief pulse of light. This strategy thus enables both rapid and sustained manipulation of neurotransmission, allowing optogenetic interrogation of neural functions over a broad range of time scales.
• 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.