1-methyl-7-(phenethylsulfanyl)quinolinium iodide

• 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: 1-methyl-7-(phenethylsulfanyl)quinolinium iodide
• 英文别名: 1-Methyl-7-(2-phenylethylsulfanyl)quinolin-1-ium;iodide
• 化学式: C₁₈H₁₈NS*I
• 分子量: 407.318
• InChiKey: AWBXHRXTQOPOKM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氟苯胺 在 硫酸 、 三乙胺 、 3-硝基苯磺酸水合物 作用下， 以 乙醇 为溶剂， 生成 1-methyl-7-(phenethylsulfanyl)quinolinium iodide
  参考文献：
  名称：

  7-Dialkylamino-1-alkylquinolinium Salts: Highly Versatile and Stable Fluorescent Probes

  摘要：

  7-Dialkylamino- and 7-alkylsulfenyl-1-alkylquinolinium salts have been synthesized using a novel synthetic approach. The key intermediate, 7-fluoro-1-methylquinolinium iodide, was shown to possess high reactivity toward nitrogen and sulfur nucleophiles, and the kinetics of this nucleophilic aromatic substitution reaction was investigated. A wide variety of compounds were synthesized and characterized spectroscopically. High fluorescence quantum yields were observed, and this was attributed to the rigid molecular architecture. The thermal and photochemical stability of a number of compounds was investigated, and it was demonstrated that 7-dialkylamino-1-methylquinolinium salts have superior stability compared to a number of hemicyanine dyes and rigid charge-transfer probes. Based on the high quantum yields, the large Stokes shifts, and in particular, the high thermal and photochemical stability, it is concluded that 7-dialkylamino-1-methylquinolinium salts are excellent color-shifting, mobility-sensitive fluorescent probes for polymer characterization and other demanding applications.

  DOI：

  10.1021/jo052441c

文献信息

• 7-Dialkylamino-1-alkylquinolinium Salts: Highly Versatile and Stable Fluorescent Probes
  作者：Otto van den Berg、Wolter F. Jager、Stephen J. Picken

  DOI：10.1021/jo052441c

  日期：2006.3.31

  7-Dialkylamino- and 7-alkylsulfenyl-1-alkylquinolinium salts have been synthesized using a novel synthetic approach. The key intermediate, 7-fluoro-1-methylquinolinium iodide, was shown to possess high reactivity toward nitrogen and sulfur nucleophiles, and the kinetics of this nucleophilic aromatic substitution reaction was investigated. A wide variety of compounds were synthesized and characterized spectroscopically. High fluorescence quantum yields were observed, and this was attributed to the rigid molecular architecture. The thermal and photochemical stability of a number of compounds was investigated, and it was demonstrated that 7-dialkylamino-1-methylquinolinium salts have superior stability compared to a number of hemicyanine dyes and rigid charge-transfer probes. Based on the high quantum yields, the large Stokes shifts, and in particular, the high thermal and photochemical stability, it is concluded that 7-dialkylamino-1-methylquinolinium salts are excellent color-shifting, mobility-sensitive fluorescent probes for polymer characterization and other demanding applications.