7-(3-morpholino-propylamino)-1-methyl-quinolinium iodide | 1219604-61-1

• 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: 7-(3-morpholino-propylamino)-1-methyl-quinolinium iodide
• 英文别名: 1-methyl-N-(3-morpholin-4-ylpropyl)quinolin-1-ium-7-amine;iodide
• CAS: 1219604-61-1
• 化学式: C₁₇H₂₄N₃O*I
• 分子量: 413.302
• InChiKey: AFLRRFUYWFYZOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  28.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(3-morpholino-propylamino)-1-methyl-quinolinium iodide 、 碘甲烷 以 甲醇 为溶剂， 反应 48.0h， 以64%的产率得到4-methyl-4-(3-(1-methylquinolinium-7-ylamino)propyl)morpholin-4-ium iodide
  参考文献：
  名称：

  Highly Sensitive Water-Soluble Fluorescent pH Sensors Based on the 7-Amino-1-methylquinolinium Chromophore

  摘要：

  Highly sensitive water-soluble fluorescent pH sensors have been synthesized employing the 7-amino1-methylquinolinium (7AMQ) chromophore. These compounds, which contained oligomethylene spacers and substituted amine receptor units, were prepared in high yields and purity by a single reaction from the readily available 7-fluoro-1-methylquinolinium iodide. Density functional theory (DFT) and semiempirical INDO/s calculations have been performed to describe the ground state and the locally excited state of the chromophore. The photophysics and the sensor characteristics have been investigated. Dissociation constants pK(A)* ranging from 5.8 to 9.9 have been obtained. An additional quenching process at pH 11, due to excited state deprotonation at N7, has been observed. Fluorescence quantum yields in the protonated "on-state" between 0.75 and 0.85 and fluorescence enhancements (FIE) between 2 and 55 were determined. These values are significantly higher than those of molecules based on other CT-chromophores that contain identical spacer-receptor units. The high fluorescence enhancements may be explained by the low rate of fluorescence (similar to 6 x 10(7) s(-1)) and the high excited state reduction potential (similar to 1.6 eV) of the 7AMQ chromophore.

  DOI：

  10.1021/jo902225k
• 作为产物：
  描述：

  7-fluoro-1-methylquinolinium iodide 、 N-(3-氨丙基)吗啉 在 三乙胺 作用下， 以83%的产率得到7-(3-morpholino-propylamino)-1-methyl-quinolinium iodide
  参考文献：
  名称：

  Highly Sensitive Water-Soluble Fluorescent pH Sensors Based on the 7-Amino-1-methylquinolinium Chromophore

  摘要：

  Highly sensitive water-soluble fluorescent pH sensors have been synthesized employing the 7-amino1-methylquinolinium (7AMQ) chromophore. These compounds, which contained oligomethylene spacers and substituted amine receptor units, were prepared in high yields and purity by a single reaction from the readily available 7-fluoro-1-methylquinolinium iodide. Density functional theory (DFT) and semiempirical INDO/s calculations have been performed to describe the ground state and the locally excited state of the chromophore. The photophysics and the sensor characteristics have been investigated. Dissociation constants pK(A)* ranging from 5.8 to 9.9 have been obtained. An additional quenching process at pH 11, due to excited state deprotonation at N7, has been observed. Fluorescence quantum yields in the protonated "on-state" between 0.75 and 0.85 and fluorescence enhancements (FIE) between 2 and 55 were determined. These values are significantly higher than those of molecules based on other CT-chromophores that contain identical spacer-receptor units. The high fluorescence enhancements may be explained by the low rate of fluorescence (similar to 6 x 10(7) s(-1)) and the high excited state reduction potential (similar to 1.6 eV) of the 7AMQ chromophore.

  DOI：

  10.1021/jo902225k

文献信息

• Highly Sensitive Water-Soluble Fluorescent pH Sensors Based on the 7-Amino-1-methylquinolinium Chromophore
  作者：Wolter F. Jager、Tessel S. Hammink、Otto van den Berg、Ferdinand C. Grozema

  DOI：10.1021/jo902225k

  日期：2010.4.2

  Highly sensitive water-soluble fluorescent pH sensors have been synthesized employing the 7-amino1-methylquinolinium (7AMQ) chromophore. These compounds, which contained oligomethylene spacers and substituted amine receptor units, were prepared in high yields and purity by a single reaction from the readily available 7-fluoro-1-methylquinolinium iodide. Density functional theory (DFT) and semiempirical INDO/s calculations have been performed to describe the ground state and the locally excited state of the chromophore. The photophysics and the sensor characteristics have been investigated. Dissociation constants pK(A)* ranging from 5.8 to 9.9 have been obtained. An additional quenching process at pH 11, due to excited state deprotonation at N7, has been observed. Fluorescence quantum yields in the protonated "on-state" between 0.75 and 0.85 and fluorescence enhancements (FIE) between 2 and 55 were determined. These values are significantly higher than those of molecules based on other CT-chromophores that contain identical spacer-receptor units. The high fluorescence enhancements may be explained by the low rate of fluorescence (similar to 6 x 10(7) s(-1)) and the high excited state reduction potential (similar to 1.6 eV) of the 7AMQ chromophore.