4-{4-[bis(2-hydroxyethyl)amino]phenylazo}benzoic acid | 177590-99-7

• 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: 4-{4-[bis(2-hydroxyethyl)amino]phenylazo}benzoic acid
• 英文别名: 4-[[4-[Bis(2-hydroxyethyl)amino]phenyl]diazenyl]benzoic acid
• CAS: 177590-99-7
• 化学式: C₁₇H₁₉N₃O₄
• 分子量: 329.356
• InChiKey: OHPGHPLNLBTWLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-{4-[bis(2-hydroxyethyl)amino]phenylazo}benzoic acid 在 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基苯酚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 62.0h， 生成 4-(4-{bis[2-(2-methylacryloyloxy)ethyl]amino}phenylazo)benzoic acid 2-methylbutyl ester
  参考文献：
  名称：

  Photoinduced Alignment of Ferroelectric Liquid Crystals Using Azobenzene Polymer Networks of Chiral Polyacrylates and Polymethacrylates

  摘要：

  Two chiral dimethacrylate and one chiral diacrylate monomer containing an azobenzene group were synthesized and dissolved in a commercial ferroelectric liquid crystal (FLC) host. With two of the monomers, thermally induced radical polymerization with the mixture exposed to linearly polarized irradiation results in a bulk alignment of FLC in the direction perpendicular to the polarization of irradiation light as a result of the photoinduced orientation of azobenzene groups related to the transcis isomerization. The monomer that is most effective for photoalignment of FLC displays a polymer network formed by strings of colloidal particles (similar to250 nm in diameter), which exerts a commanding effect on the alignment of FLC as being able to reorient the FLC by changing the polarization direction of subsequent irradiation. The study suggests that the network of colloidal particles is isotropic and that the photoalignment of azobenzene moieties on the large surface of the network dictates the alignment of FLC.

  DOI：

  10.1021/ma034886d
• 作为产物：
  描述：

  N,N-二羟乙基苯胺 、 苯佐卡因 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 甲醇 为溶剂， 反应 2.5h， 生成 4-{4-[bis(2-hydroxyethyl)amino]phenylazo}benzoic acid
  参考文献：
  名称：

  Dye-incorporated water-soluble polymer via click triazole formation

  摘要：

  A click triazole-polymerization is proposed for the synthesis of a water-soluble polymer dye. 4,4'-Diazidostilbene-2,2'-disulfonate (DASS) sodium salt reacted with a diacetylenic derivative of para-methyl red (PMR) in water, which was catalyzed by copper (I) ion or accelerated under ultrasound irradiation. DASS formed a soluble polymer with a carboxylate salt of PMR showing a water solubility of 120 g/100 mL but it generated an insoluble polymer with an alkyl ammonium salt. The prepared polymeric dye underwent color transition at pH 5-6, which is higher than that of PMR and similar to that of ortho-methyl red (OMR). The quinonoid canonical structure of PMR generated a purple water solution and was dominant in the polymer solution at pH below 5. Intra-molecular hydrogen bonding between the triazoles and azo nitrogens was presumed to have induced the formation of the quinonoid structure. The color change of the polymer was reproducible during successive up/down pH cycles. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.01.012

文献信息

• Dye-incorporated water-soluble polymer via click triazole formation
  作者：Byungkwon Jang、Sung Yoon Kim、Jung Yun Do

  DOI：10.1016/j.dyepig.2012.01.012

  日期：2012.8

  A click triazole-polymerization is proposed for the synthesis of a water-soluble polymer dye. 4,4'-Diazidostilbene-2,2'-disulfonate (DASS) sodium salt reacted with a diacetylenic derivative of para-methyl red (PMR) in water, which was catalyzed by copper (I) ion or accelerated under ultrasound irradiation. DASS formed a soluble polymer with a carboxylate salt of PMR showing a water solubility of 120 g/100 mL but it generated an insoluble polymer with an alkyl ammonium salt. The prepared polymeric dye underwent color transition at pH 5-6, which is higher than that of PMR and similar to that of ortho-methyl red (OMR). The quinonoid canonical structure of PMR generated a purple water solution and was dominant in the polymer solution at pH below 5. Intra-molecular hydrogen bonding between the triazoles and azo nitrogens was presumed to have induced the formation of the quinonoid structure. The color change of the polymer was reproducible during successive up/down pH cycles. (C) 2012 Elsevier Ltd. All rights reserved.
• Photoinduced Alignment of Ferroelectric Liquid Crystals Using Azobenzene Polymer Networks of Chiral Polyacrylates and Polymethacrylates
  作者：Steve Leclair、Lizamma Mathew、Martin Giguère、Shahrokh Motallebi、Yue Zhao

  DOI：10.1021/ma034886d

  日期：2003.12.1

  Two chiral dimethacrylate and one chiral diacrylate monomer containing an azobenzene group were synthesized and dissolved in a commercial ferroelectric liquid crystal (FLC) host. With two of the monomers, thermally induced radical polymerization with the mixture exposed to linearly polarized irradiation results in a bulk alignment of FLC in the direction perpendicular to the polarization of irradiation light as a result of the photoinduced orientation of azobenzene groups related to the transcis isomerization. The monomer that is most effective for photoalignment of FLC displays a polymer network formed by strings of colloidal particles (similar to250 nm in diameter), which exerts a commanding effect on the alignment of FLC as being able to reorient the FLC by changing the polarization direction of subsequent irradiation. The study suggests that the network of colloidal particles is isotropic and that the photoalignment of azobenzene moieties on the large surface of the network dictates the alignment of FLC.