4-methoxy-N-(2-bromoethyl)-1,8-naphthalimide | 171280-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-methoxy-N-(2-bromoethyl)-1,8-naphthalimide
• 英文别名: 2-(2-Bromoethyl)-6-methoxybenzo[de]isoquinoline-1,3-dione；2-(2-bromoethyl)-6-methoxybenzo[de]isoquinoline-1,3-dione
• CAS: 171280-73-2
• 化学式: C₁₅H₁₂BrNO₃
• 分子量: 334.169
• InChiKey: AWSSLOMUYDYZAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(2-bromoethyl)-1,8-naphthalimide 、 2-(4-Hydroxyphenyl)-6-(4-methylpiperazin-1-yl)benzo[de]isoquinoline-1,3-dione 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以15%的产率得到2-[4-[2-(6-Methoxy-1,3-dioxobenzo[de]isoquinolin-2-yl)ethoxy]phenyl]-6-(4-methylpiperazin-1-yl)benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Design, synthesis and pH sensing properties of novel 1,8-naphtalimide-based bichromophoric system

  摘要：

  In this work we report on the design, synthesis and sensor properties of a novel bichromophoric sensor system based on 1,8-naphthalimide fluorophores. The synthesized dyad was configured as a fluorescent wavelength-shifting energy transfer chromophore. The novel donor-acceptor system contains blue emitting 4-methoxy-1,8-naphthalimide donor dye, capable of both absorbing light and efficiently transferring the energy to yellow-green emitting 4-N-methylpiperazinyl-1,8-naphthalimide acceptor. The energy-transfer efficiency in the dyad system was calculated to be more than 99%. The acceptor unit in the donor-acceptor system was also designed as a PET based sensor according to the "fluorophore-spacer-receptor" model. The fluorescence behaviour of the bichromophoric system was investigated as a function of pH. The fluorescence enhancement of the novel dyad in acidic media was more than 29 times indicating the high ability of the system to act as an efficient pH chemosensor. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2011.05.012
• 作为产物：
  描述：

  2-(2-hydroxyethyl)-6-methoxy-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 四溴化碳 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以74%的产率得到4-methoxy-N-(2-bromoethyl)-1,8-naphthalimide
  参考文献：
  名称：

  Design, synthesis and pH sensing properties of novel 1,8-naphtalimide-based bichromophoric system

  摘要：

  In this work we report on the design, synthesis and sensor properties of a novel bichromophoric sensor system based on 1,8-naphthalimide fluorophores. The synthesized dyad was configured as a fluorescent wavelength-shifting energy transfer chromophore. The novel donor-acceptor system contains blue emitting 4-methoxy-1,8-naphthalimide donor dye, capable of both absorbing light and efficiently transferring the energy to yellow-green emitting 4-N-methylpiperazinyl-1,8-naphthalimide acceptor. The energy-transfer efficiency in the dyad system was calculated to be more than 99%. The acceptor unit in the donor-acceptor system was also designed as a PET based sensor according to the "fluorophore-spacer-receptor" model. The fluorescence behaviour of the bichromophoric system was investigated as a function of pH. The fluorescence enhancement of the novel dyad in acidic media was more than 29 times indicating the high ability of the system to act as an efficient pH chemosensor. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2011.05.012

文献信息

• Design, synthesis and pH sensing properties of novel 1,8-naphtalimide-based bichromophoric system
  作者：Nevena V. Marinova、Nikolai I. Georgiev、Vladimir B. Bojinov

  DOI：10.1016/j.jphotochem.2011.05.012

  日期：2011.7

  In this work we report on the design, synthesis and sensor properties of a novel bichromophoric sensor system based on 1,8-naphthalimide fluorophores. The synthesized dyad was configured as a fluorescent wavelength-shifting energy transfer chromophore. The novel donor-acceptor system contains blue emitting 4-methoxy-1,8-naphthalimide donor dye, capable of both absorbing light and efficiently transferring the energy to yellow-green emitting 4-N-methylpiperazinyl-1,8-naphthalimide acceptor. The energy-transfer efficiency in the dyad system was calculated to be more than 99%. The acceptor unit in the donor-acceptor system was also designed as a PET based sensor according to the "fluorophore-spacer-receptor" model. The fluorescence behaviour of the bichromophoric system was investigated as a function of pH. The fluorescence enhancement of the novel dyad in acidic media was more than 29 times indicating the high ability of the system to act as an efficient pH chemosensor. (C) 2011 Elsevier B.V. All rights reserved.