4-(8-羟基-5-喹啉基偶氮)苯磺酸 | 574-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 4-(8-羟基-5-喹啉基偶氮)苯磺酸
• 英文名称: 4-[(8-hydroxy-5-quinolinyl)azo]-benzenesulfonic acid
• 英文别名: 4-(8-hydroxyquinoline-5-azo)benzensulfonic acid；4-sulfophenyl-(8-hydroxy-5-quinolinyl)diazine；5-(p-Sulfophenylazo)-8-quinolinol；4-[(8-hydroxyquinolin-5-yl)diazenyl]benzenesulfonic acid
• CAS: 574-70-9
• 化学式: C₁₅H₁₁N₃O₄S
• 分子量: 329.336
• InChiKey: JIAGGSRRAAHALT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  mercury(II) diacetate 、 4-(8-羟基-5-喹啉基偶氮)苯磺酸 以 甲苯 为溶剂， 以79.1%的产率得到
  参考文献：
  名称：

  El-Sawi, E.; Moti, F.A.; El-Messary, S., Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 1, p. 69 - 74

  摘要：

  DOI：
• 作为产物：
  描述：

  8-羟基喹啉 、 对氨基苯磺酸 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以35%的产率得到4-(8-羟基-5-喹啉基偶氮)苯磺酸
  参考文献：
  名称：

  锂诱导的超分子水凝胶。

  摘要：

  我们描述了由环糊精染料制成的新型各向异性超分子凝胶，其中物理胶凝是通过锂盐完成的。流变实验揭示了水凝胶的弹性行为，高离子电导率代表了凝胶基质内部离子的良好迁移性。

  DOI：

  10.1039/c1cc10532a

文献信息

• One-Pot Diazo Coupling Reaction Under Microwave Irradiation in the Absence of Solvent
  作者：Jin Jin、Zhong Wen、Jiang Long、Yongmei Wang、Teruo Matsuura、Jiben Meng

  DOI：10.1080/00397910008087094

  日期：2000.3

  Abstract Diazotization and coupling reactions were carried out in one pot by inducing with microwave irradiation in the absence of solvent.

  摘要 重氮化和偶联反应在无溶剂微波诱导下在一锅内进行。
• Preparation of coordination polymers with 8-hydroxyquinoline azo benzensulfonic acid as a planar multidentate ligand and the study of their photochemical and photo-stability properties
  作者：Hong-Xia Chen、Feng Zhou、Yong Ma、Xiao-Ping Xu、Jian-Feng Ge、Yong Zhang、Qing-Feng Xu、Jian-Mei Lu

  DOI：10.1039/c2dt32381h

  日期：——

  The combination of ditopic ligand 4-(8-hydroxyquinoline-5-azo)-benzensulfonic acid (H2QBS) with metal ions (M = Na+, Pb2+, Zn2+, Mn2+, Cd2+) leads to five different coordination polymers (CPs): [Na2(QBS)(H2O)2]n (1, 3D framework), [Pb(QBS)(DMSO)]·2(iPrOH)}n (2·2iPrOH, 2D layer), [Zn(QBS)(DMSO)]·2DMSO}n (3·2DMSO, 1D chain), [Mn(QBS)(iPrOH)(DMSO)]n (4, 1D ladder), and [Cd2(QBS)2(DMSO)2(H2O)4]n (5, 1D chain). All compounds were characterized by FT-IR, elemental analysis and TG analysis, and their structures were determined by single crystal X-ray diffraction. As expected, H2QBS acted as a multimode ligand and the azo bond in the trans-form existed in all compounds. Their photo-stability was also studied using irradiation from different light sources (450 nm, 365 nm and 254 nm). Under blue light (450 nm) and lower energy UV light (365 nm), the colors of all compounds were well preserved and the absorption spectra show slight changes. However, when irradiated using higher energy UV light (254 nm), the coordination interaction between the metal ions and the ligand was disassociated and the color faded.

  双位配体 4-(8-羟基喹啉-5-偶氮)-苯磺酸 (H2QBS) 与金属离子 (M = Na+、Pb2+、Zn2+、Mn2+、Cd2+) 的结合产生五种不同的配位聚合物 (CP)：[Na2 (QBS)(H2O)2]n (1, 3D 框架), [Pb(QBS)(DMSO)]·2(iPrOH)}n (2·2iPrOH, 2D 层), [Zn(QBS)(DMSO) )]·2DMSO}n（3·2DMSO，1D 链）、[Mn(QBS)(iPrOH)(DMSO)]n（4，1D 梯形）和 [Cd2(QBS)2(DMSO)2(H2O)4 ]n（5，一维链）。所有化合物均通过FT-IR、元素分析和TG分析进行了表征，并通过单晶X射线衍射确定了其结构。正如预期的那样，H2QBS 充当多模式配体，并且反式偶氮键存在于所有化合物中。还使用不同光源（450 nm、365 nm 和 254 nm）的照射研究了它们的光稳定性。在蓝光（450 nm）和较低能量的紫外光（365 nm）下，所有化合物的颜色都保存完好，吸收光谱显示出轻微的变化。然而，当使用更高能量的紫外线（254 nm）照射时，金属离子和配体之间的配位相互作用被解离，颜色褪色。
• A new zinc coordination polymer constructed from 4-[(8-hydroxy-5-quinolinyl)azo]-benzenesulfonic acid: synthesis, structure, and photoelectrical property
  作者：Ya-Nan Luo、Hui-Ying Jiang、Zhi-Chen Liu、Li-Ying Yu、Xiao-Yang Yu

  DOI：10.1007/s11224-018-1079-3

  日期：2018.8

  One new supramolecular compound based on H2L (H2L = 4-[(8-hydroxy-5-quinolinyl)azo]-benzenesulfonic acid, C15H11O4N3S), [Zn3L2(OH)2(H2O)6]n (1), has been synthesized by hydrothermal technique. Compound 1 exhibits a one-dimensional (1-D) double-chain structure. Compound 1 is the first example of an azo complex used to co-sensitize TiO2 photoanode with Ru dyes (N719, N3). In the tandem structure of compound

  合成了一种基于 H2L (H2L = 4-[(8-hydroxy-5-quinolinyl)azo]-苯磺酸，C15H11O4N3S)，[Zn3L2(OH)2(H2O)6]n (1) 的新型超分子化合物通过水热技术。化合物 1 表现出一维 (1-D) 双链结构。化合物 1 是用于共敏化 TiO2 光阳极与 Ru 染料（N719，N3）的偶氮络合物的第一个例子。在化合物1/N719/TiO2的串联结构中，化合物1对光电转换效率的提高起到了显着的作用，它与N719一起改变了能级。结果表明，化合物1/N719/TiO2太阳能电池在标准全球AM 1.5太阳辐照条件下表现出优异的光伏性能，光电转换效率为7.1%。
• Colorimetric sensing of Cu2+ using a cyclodextrin–dye rotaxane
  作者：Jong S. Park、Sooyeon Jeong、Seongkook Dho、Myungwon Lee、Chungkun Song

  DOI：10.1016/j.dyepig.2010.02.003

  日期：2010.9

  A dye rotaxane having 8-hydroxyquinoline as coupling component was prepared in the presence of a-cyclodextrin and its structure identified using NMR. The dye rotaxane displayed high color strength regardless of the solvent used and responded to changes in pH based on tautomeric equilibrium, without any interference by the cyclodextrin macrocycle. Compared to the non-rotaxanated forms, the dye rotaxane displayed a characteristic spectral response to the presence of Cu2+ which was attributed to the formation of a polymeric, metal dye rotaxane complex which was of high solubility because of the presence of cyclodextrin. Thus, this approach can clearly be used as a facile and efficient sensor for copper ions. (C) 2010 Elsevier Ltd. All rights reserved.
• El-Sawi, E.; Moti, F.A.; El-Messary, S., Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 1, p. 69 - 74
  作者：El-Sawi, E.、Moti, F.A.、El-Messary, S.

  DOI：——

  日期：——