2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g′]diquinoxaline | 1394921-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g′]diquinoxaline
• 英文别名: 2,3,15,16-Tetrakis(pyridin2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g']diquinoxaline；13,14,30,31-tetrapyridin-2-yl-2,5,8,19,22,25-hexaoxa-12,15,29,32-tetrazapentacyclo[24.8.0.09,18.011,16.028,33]tetratriaconta-1(26),9(18),10,12,14,16,27,29,31,33-decaene
• CAS: 1394921-04-0
• 化学式: C₄₄H₃₆N₈O₆
• 分子量: 772.82
• InChiKey: NQLFVLJNIWQFEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  58
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g′]diquinoxaline 、 zinc(II) chloride 以 二氯甲烷 、 乙腈 为溶剂， 反应 504.0h， 生成 Zn2Cl4(2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g′]diquinoxaline)
  参考文献：
  名称：

  Ratiometric and Selective Fluorescent Sensor for Zn²⁺ as an “Off–On–Off” Switch and Logic Gate

  摘要：

  A new chemosensor, 2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g']diquinoxaline (1), containing 2,3-bis(pyridin-2-yl)quinoxaline and crown ether moieties, has been designed and found to be a ratiometric and selective fluorescent detector of Zn2+ over a wide range of tested metal ions. The addition of Zn2+ to the solution of 1 in acetonitrile induced the formation of a 1:2 ligand-metal complex, 1-Zn2+, which exhibits a remarkable enhanced fluorescent emission centered at 460 nm, with the disappearance of the fluorescent emission of 1 centered at 396 nm due to the mechanism of internal charge transfer. In contrast, the presence of K+ results in the fluorescence quenching of 1 and 1-Zn2+ through the photoinduced electron-transfer mechanism. These results demonstrate that 1 can perform as not only an INHIBIT logic gate but also an "off-on-off" molecular switch triggered by Zn2+ and K+. The structure of complex 1-Zn2+ has been characterized by single-crystal X-ray crystallography, mass spectrometry, and H-1 NMR titration experiments. Density functional theory calculation results on 1 and the 1-Zn2+ complex are well consistent with the experimental results.

  DOI：

  10.1021/ic300738e
• 作为产物：
  描述：

  二苯并-18-冠醚-6 在 硫酸 、 palladium on activated charcoal 、 硝酸 、 溶剂黄146 、 肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g′]diquinoxaline
  参考文献：
  名称：

  Ratiometric and Selective Fluorescent Sensor for Zn²⁺ as an “Off–On–Off” Switch and Logic Gate

  摘要：

  A new chemosensor, 2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g']diquinoxaline (1), containing 2,3-bis(pyridin-2-yl)quinoxaline and crown ether moieties, has been designed and found to be a ratiometric and selective fluorescent detector of Zn2+ over a wide range of tested metal ions. The addition of Zn2+ to the solution of 1 in acetonitrile induced the formation of a 1:2 ligand-metal complex, 1-Zn2+, which exhibits a remarkable enhanced fluorescent emission centered at 460 nm, with the disappearance of the fluorescent emission of 1 centered at 396 nm due to the mechanism of internal charge transfer. In contrast, the presence of K+ results in the fluorescence quenching of 1 and 1-Zn2+ through the photoinduced electron-transfer mechanism. These results demonstrate that 1 can perform as not only an INHIBIT logic gate but also an "off-on-off" molecular switch triggered by Zn2+ and K+. The structure of complex 1-Zn2+ has been characterized by single-crystal X-ray crystallography, mass spectrometry, and H-1 NMR titration experiments. Density functional theory calculation results on 1 and the 1-Zn2+ complex are well consistent with the experimental results.

  DOI：

  10.1021/ic300738e

文献信息

• Ratiometric and Selective Fluorescent Sensor for Zn²⁺ as an “Off–On–Off” Switch and Logic Gate
  作者：Ya-Ping Li、Hua-Rong Yang、Qiang Zhao、Wei-Chao Song、Jie Han、Xian-He Bu

  DOI：10.1021/ic300738e

  日期：2012.9.17

  A new chemosensor, 2,3,15,16-tetrakis(pyridin-2-yl)-7,8,10,11,20,21,23,24-octahydro[1,4,7,10,13,16]-hexaoxacyclooctadecino[2,3-g:11,12-g']diquinoxaline (1), containing 2,3-bis(pyridin-2-yl)quinoxaline and crown ether moieties, has been designed and found to be a ratiometric and selective fluorescent detector of Zn2+ over a wide range of tested metal ions. The addition of Zn2+ to the solution of 1 in acetonitrile induced the formation of a 1:2 ligand-metal complex, 1-Zn2+, which exhibits a remarkable enhanced fluorescent emission centered at 460 nm, with the disappearance of the fluorescent emission of 1 centered at 396 nm due to the mechanism of internal charge transfer. In contrast, the presence of K+ results in the fluorescence quenching of 1 and 1-Zn2+ through the photoinduced electron-transfer mechanism. These results demonstrate that 1 can perform as not only an INHIBIT logic gate but also an "off-on-off" molecular switch triggered by Zn2+ and K+. The structure of complex 1-Zn2+ has been characterized by single-crystal X-ray crystallography, mass spectrometry, and H-1 NMR titration experiments. Density functional theory calculation results on 1 and the 1-Zn2+ complex are well consistent with the experimental results.