9-(9'-anthracenecarbonyl)-3,6,12,15-tetrathia-9-azaheptadecane

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(9'-anthracenecarbonyl)-3,6,12,15-tetrathia-9-azaheptadecane
• 英文别名: N,N-bis[2-(2-ethylsulfanylethylsulfanyl)ethyl]anthracene-9-carboxamide
• 化学式: C₂₇H₃₅NOS₄
• 分子量: 517.845
• InChiKey: MHTCIQVORVAEMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9-蒽甲酰氯 、 3,6,12,15-tetrathia-9-monoazaheptadecane 在 potassium carbonate 作用下， 以 苯 为溶剂， 反应 3.0h， 以34.8%的产率得到9-(9'-anthracenecarbonyl)-3,6,12,15-tetrathia-9-azaheptadecane
  参考文献：
  名称：

  Silver Ion Selective Fluoroionophores Based on Anthracene-Linked Polythiazaalkane or Polythiaalkane Derivatives

  摘要：

  A dozen novel fluoroionophores have been synthesized which are polythiazaalkane and polythiaalkane derivatives coupled with an anthracene moiety by methyl, carbonyl, or methylphenylene bridging groups. The protonation and metal ion complexation behavior of analogues were examined in 1,4-dioxane--water solutions spectrophotometrically and spectrophotofluorometrically. The fluoroionophores, 1, 2, 5, and 6 contain basic nitrogen atoms and quench the fluorescence in the free forms because of photoinduced electron transfer (PET) from a nitrogen atom to a photoexcited anthracene unit. The fluorescence was recovered by the protonation on the nitrogen atom. The fluorescence intensities of the other fluoroionophores used here were not dependent on the pH of the solution. On the complexation of the protonated fluoroionophores 1, 2, 5, and 6 with metal ions under the acidic condition, the fluorescence intensities were decreased by the addition of silver ion selectively. Under the same conditions, the other fluoroionophores exhibited a decrease of the fluorescence intensity with the addition of silver ion selectively. These results imply that the fluoroionophores could form complexes and release a proton from the nitrogen atom of the protonated fluoroionophores. The quenching of the fluorescence of the complexed fluoroionophores 3, 4, 7, and 8-12 could be caused by the interaction of a silver ion with a ct-electron of the anthracene unit. The degree of spectral change on the complexation with silver ion is primarily dependent on the strength of the interaction of the bound silver ion with nitrogen atom, far 1, 2, 5, and 6, or with a pi-electron of the anthracene unit, for 3, 4, 7, and 8-12.

  DOI：

  10.1021/jo9819584

文献信息

• Silver Ion Selective Fluoroionophores Based on Anthracene-Linked Polythiazaalkane or Polythiaalkane Derivatives
  作者：Junichi Ishikawa、Hidefumi Sakamoto、Shintaro Nakao、Hiroko Wada

  DOI：10.1021/jo9819584

  日期：1999.3.1

  A dozen novel fluoroionophores have been synthesized which are polythiazaalkane and polythiaalkane derivatives coupled with an anthracene moiety by methyl, carbonyl, or methylphenylene bridging groups. The protonation and metal ion complexation behavior of analogues were examined in 1,4-dioxane--water solutions spectrophotometrically and spectrophotofluorometrically. The fluoroionophores, 1, 2, 5, and 6 contain basic nitrogen atoms and quench the fluorescence in the free forms because of photoinduced electron transfer (PET) from a nitrogen atom to a photoexcited anthracene unit. The fluorescence was recovered by the protonation on the nitrogen atom. The fluorescence intensities of the other fluoroionophores used here were not dependent on the pH of the solution. On the complexation of the protonated fluoroionophores 1, 2, 5, and 6 with metal ions under the acidic condition, the fluorescence intensities were decreased by the addition of silver ion selectively. Under the same conditions, the other fluoroionophores exhibited a decrease of the fluorescence intensity with the addition of silver ion selectively. These results imply that the fluoroionophores could form complexes and release a proton from the nitrogen atom of the protonated fluoroionophores. The quenching of the fluorescence of the complexed fluoroionophores 3, 4, 7, and 8-12 could be caused by the interaction of a silver ion with a ct-electron of the anthracene unit. The degree of spectral change on the complexation with silver ion is primarily dependent on the strength of the interaction of the bound silver ion with nitrogen atom, far 1, 2, 5, and 6, or with a pi-electron of the anthracene unit, for 3, 4, 7, and 8-12.