5-(二乙基氨基)-2-(1,3-噻唑-2-基偶氮)苯酚 | 101412-82-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 5-(二乙基氨基)-2-(1,3-噻唑-2-基偶氮)苯酚
• 英文名称: 1-(Thiazol-2-ylazo)-5-diethylamino-phenol
• 英文别名: 2-(2-thiazolylazo)-5-diethylaminophenol；5-(diethylamino)-2-(2-thiazolylazo)phenol；5-diethylamino-2-thiazol-2-ylazo-phenol；5-(diethylamino)-2-(1,3-thiazol-2-yldiazenyl)phenol
• CAS: 101412-82-2；10558-42-6
• 化学式: C₁₃H₁₆N₄OS
• 分子量: 276.362
• InChiKey: PEHZNRJWAFFDNK-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  464.9±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  89.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  zinc(II) acetate dihydrate 、 5-(二乙基氨基)-2-(1,3-噻唑-2-基偶氮)苯酚 以 甲醇 、 二氯甲烷 为溶剂， 以53%的产率得到[Zn3(5-(diethylamino)-2-(2-thiazolylazo)phenol(-H))2(acetate)4]
  参考文献：
  名称：

  由噻唑基染料和醋酸锌组装而成的稳定三核锌簇：制备、结构表征和光谱研究

  摘要：

  以高产率合成了含有潜在三齿结合位点的 thiazolylazo 染料 5-(二乙氨基)-2-(2-thiazolylazo) 苯酚 (HL)。在溶液中，醋酸锌和去质子化配体 L- 的反应导致超分子三核物质 [Zn3L2(OAc)4] (1) 的瞬时形成。溶液中的 UV/Vis 和 1H NMR 光谱滴定实验证实，配体和锌盐彼此自发相互作用，仅产生金属与配体比为 3:2 的多金属配合物。本文报道了配体和配位配合物的晶体结构。HL 的芳香部分是平面的，重要的是，这里观察到的分子间C–H…π氢键和噻唑环-S…π弱相互作用应该是正交空间群P212121的原因。1的结构揭示了线性三核锌簇。两个 L- 单元以 N2O 三齿模式连接到三个锌原子，四个乙酸根阴离子螯合到三个金属中心作为桥，产生两个五配位和一个六配位锌中心。由此产生的桥接 Zn1-Zn2-Zn1A 阵列是线性对称的，非键合 Zn...Zn 距离为

  DOI：

  10.1002/ejic.200500451

文献信息

• Investigation of third-order nonlinearity of an azo dye and its metal-substituted compounds
  作者：Saijun Wu、Wei Qian、Zongju Xia、Yinghua Zou、Shuangqing Wang、Shuyin Shen、Huijun Xu

  DOI：10.1016/s0009-2614(00)01135-0

  日期：2000.11

  The real part of third-order optical nonlinearity of an azo dye (2-(2-thiazolylazo)-5-diethylaminophenol TAEP) and those of its copper- and cobalt-substituted compounds are measured by using femtosecond optical heterodyne optical Kerr gate technique at the wavelength of 647 nm. All the values are found to be negative. Those of Cu- and Co-substituted compounds are found to be larger than that of the metal-free dye by two and three orders of magnitude, respectively. A negative gamma (eff) as large as 10(-29) esu is found in Co complex. We use a three-level model to characterize the nonlinear process, and suggest that pi -electron delocalization in metal complex leads to an enhancement. (C) 2000 Elsevier Science B.V. All rights reserved.
• Syntheses, characterization and third-order nonlinear optical properties of a class of thiazolylazo-based metal complexes
  作者：Guoqi Zhang、Shuangqing Wang、Jin Shi Ma、Guoqiang Yang

  DOI：10.1016/j.ica.2011.11.045

  日期：2012.4

  The reactions of a thiazolylazo ligand, 2-(2-thiazolylazo)-5-diethylaminophenol (HL) with zinc(II) chloride, nickel(II) acetate and cobalt(II) acetate resulted in the formation of the corresponding mononuclear coordination complexes, 1-3, both in solution and in the solid state. UV-Vis titration experiments in solution confirmed that the ligand and given metal salts interacted spontaneously with each other, producing exclusively mononuclear complexes with a metal/ligand ratio of 1:2. The solid-state structures of complexes 1 and 2 were determined by single-crystal X-ray diffraction analysis. In the structure of 1, zinc(II) ion is tetra-coordinate to two N atoms from the thiazolyl groups of two distinct HL ligands and two chloride counterions with a distorted tetrahedral geometry. In the structure of 2, the nickel ion is bound to four N atoms from both the thiazolyl groups and azo group moieties, and two O atoms from the phenol groups with a hexacoordinated mode. The third-order nonlinear optical (NLO) properties of both HL and 1-3 were studied by Z-scan technique in CHCl3 solution. The results showed that all four compounds exhibited strong nonlinear refraction, while complex 2 featured both large nonlinear absorption and refraction. The nonlinear refractive index values n(2) of four compounds vary in the range of -1.20 x 10(-18) to -3.42 x 10(-18) m(2)/W. Their hyperpolarizability gamma values are determined to be 2.01 x 10(-35), 1.13 x 10(-34), 2.09 x 10(-34), and 7.83 x 10(-34) esu for HL and 1-3, respectively, indicating that metal chelating did lead to considerable enhancement in third-order optical nonlinearities. (C) 2011 Elsevier B. V. All rights reserved.