2-[[2-[2-[2-[2-[(8-Hydroxyquinolin-2-yl)methylamino]phenoxy]ethoxy]ethoxy]anilino]methyl]quinolin-8-ol | 1358939-63-5

• 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
• 英文名称: 2-[[2-[2-[2-[2-[(8-Hydroxyquinolin-2-yl)methylamino]phenoxy]ethoxy]ethoxy]anilino]methyl]quinolin-8-ol
• 英文别名: 2-[[2-[2-[2-[2-[(8-hydroxyquinolin-2-yl)methylamino]phenoxy]ethoxy]ethoxy]anilino]methyl]quinolin-8-ol
• CAS: 1358939-63-5
• 化学式: C₃₆H₃₄N₄O₅
• 分子量: 602.69
• InChiKey: XEYDEJKZOSKHHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[[2-[2-[2-[2-[(8-Hydroxyquinolin-2-yl)methylamino]phenoxy]ethoxy]ethoxy]anilino]methyl]quinolin-8-ol 、 四甲基氢氧化铵 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Novel emissive podands based on 8-OH-quinoline: Synthesis, fluorescence materials, DFT and complexation studies

  摘要：

  Two novel chemosensors with podand structures (L-1 and L-2) derived from 1,5-bis(2-aminophenoxy)-3-oxopenthane bearing two flexible 8-hydroxyquinoline units have been synthesized and characterized. Several nitrate complexes of transition (Cu2+), post-transition (Zn2+) and lanthanide (Eu3+ and Sm3+) metal ions have been synthesized with tetrafluoroborate salts and characterized. In order to study their potential utility as fluorescent probes, the coordination ability of chemosensors (L-1 and L-2) towards those metal ions has been explored in solution (by UV-Vis and emission spectroscopy) and in gas phase (by MALDI mass spectrometry).Density functional theory has been employed to explore the emission properties of the three-protonation states of the chemosensor. From this study, the anomalous red shift observed in the fluorescence spectra of the dianionic sensors can be attributed to subtle structural differences between their anionic and dianionic forms. Furthermore, a plausible explanation for the low fluorescence of the neutral form is provided in the form of a non-radiative relaxation involving the imine double-bond isomerization.All new compounds have been characterized by microanalysis, melting points, IR, UV-Vis and fluorescence emission spectroscopy and MALDI-TOF-mass spectrometry. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.09.018
• 作为产物：
  描述：

  8-羟基喹啉-2-甲醛 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2-[[2-[2-[2-[2-[(8-Hydroxyquinolin-2-yl)methylamino]phenoxy]ethoxy]ethoxy]anilino]methyl]quinolin-8-ol
  参考文献：
  名称：

  Novel emissive podands based on 8-OH-quinoline: Synthesis, fluorescence materials, DFT and complexation studies

  摘要：

  Two novel chemosensors with podand structures (L-1 and L-2) derived from 1,5-bis(2-aminophenoxy)-3-oxopenthane bearing two flexible 8-hydroxyquinoline units have been synthesized and characterized. Several nitrate complexes of transition (Cu2+), post-transition (Zn2+) and lanthanide (Eu3+ and Sm3+) metal ions have been synthesized with tetrafluoroborate salts and characterized. In order to study their potential utility as fluorescent probes, the coordination ability of chemosensors (L-1 and L-2) towards those metal ions has been explored in solution (by UV-Vis and emission spectroscopy) and in gas phase (by MALDI mass spectrometry).Density functional theory has been employed to explore the emission properties of the three-protonation states of the chemosensor. From this study, the anomalous red shift observed in the fluorescence spectra of the dianionic sensors can be attributed to subtle structural differences between their anionic and dianionic forms. Furthermore, a plausible explanation for the low fluorescence of the neutral form is provided in the form of a non-radiative relaxation involving the imine double-bond isomerization.All new compounds have been characterized by microanalysis, melting points, IR, UV-Vis and fluorescence emission spectroscopy and MALDI-TOF-mass spectrometry. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.09.018

文献信息

• Novel emissive podands based on 8-OH-quinoline: Synthesis, fluorescence materials, DFT and complexation studies
  作者：Javier Fernández-Lodeiro、Cristina Núñez、Olalla Nieto Faza、Jose Luis Capelo、Carlos Lodeiro、J. Sérgio Seixas de Melo、Carlos Silva López

  DOI：10.1016/j.ica.2011.09.018

  日期：2012.2

  Two novel chemosensors with podand structures (L-1 and L-2) derived from 1,5-bis(2-aminophenoxy)-3-oxopenthane bearing two flexible 8-hydroxyquinoline units have been synthesized and characterized. Several nitrate complexes of transition (Cu2+), post-transition (Zn2+) and lanthanide (Eu3+ and Sm3+) metal ions have been synthesized with tetrafluoroborate salts and characterized. In order to study their potential utility as fluorescent probes, the coordination ability of chemosensors (L-1 and L-2) towards those metal ions has been explored in solution (by UV-Vis and emission spectroscopy) and in gas phase (by MALDI mass spectrometry).Density functional theory has been employed to explore the emission properties of the three-protonation states of the chemosensor. From this study, the anomalous red shift observed in the fluorescence spectra of the dianionic sensors can be attributed to subtle structural differences between their anionic and dianionic forms. Furthermore, a plausible explanation for the low fluorescence of the neutral form is provided in the form of a non-radiative relaxation involving the imine double-bond isomerization.All new compounds have been characterized by microanalysis, melting points, IR, UV-Vis and fluorescence emission spectroscopy and MALDI-TOF-mass spectrometry. (C) 2011 Elsevier B.V. All rights reserved.