N-(11-bromoundecyl)-2-methylprop-2-enamide | 1372718-50-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(11-bromoundecyl)-2-methylprop-2-enamide
• CAS: 1372718-50-7
• 化学式: C₁₅H₂₈BrNO
• 分子量: 318.297
• InChiKey: JXKOFJMZEBMGJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(11-bromoundecyl)-2-methylprop-2-enamide 在 氯磺酸 、 2,6-二叔丁基-4-甲基苯酚 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.25h， 生成 5,5-difluoro-10-(4-((11-methacrylamidoundecyl)oxy)phenyl)-1,3,7,9-tetramethyl-8-sulfo-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
  参考文献：
  名称：

  One-Pot Production of Fluorescent Surface-Labeled Polymeric Nanoparticles via Miniemulsion Polymerization with Bodipy Surfmers

  摘要：

  New molecules combining the functionalities of surface activity, polymerizability, and fluorescent properties within one molecule that could be seen as a fluorescent surfmer (surfactant and monomer) were successfully synthesized. A long hydrocarbon tail capped with a methacrylamide unit was anchored to a mono- or double-sutfonated Bodipy core. Time-resolved fluorescence measurements in aqueous solutions of the dyes enable one to trace the micelle formation and to find strong polarity dependence of fluorescence properties of the dyes. By using these molecules, polystyrene nanoparticles with fluorescent interfaces were synthesized via miniemulsion polymerization. The surfmers can be used alone or as surfactant additional to sodium dodecyl sulfate that provides stable emulsions and dispersions with a wide range (100-250 nm) of realizable particle sizes after polymerization. All synthesized nanoparticles showed bright fluorescence and can be easily investigated with conventional fluorescent confocal microscopy. Only the fluorescence of particles with double-sulfonated surfmer used is strongly sensitive to fluorescent quenchers as sodium iodide or methyl viologene dissolved in the continuous phase. In contrast, the fluorescence of nanoparticles labeled with the monosulfonated surfmer is only weakly quenched that might be explained by specific orientation of the Bodipy core at particle/water interface.

  DOI：

  10.1021/ma300090a
• 作为产物：
  描述：

  11-aminoundecan-1-ol 在 氢溴酸 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 N-(11-bromoundecyl)-2-methylprop-2-enamide
  参考文献：
  名称：

  One-Pot Production of Fluorescent Surface-Labeled Polymeric Nanoparticles via Miniemulsion Polymerization with Bodipy Surfmers

  摘要：

  New molecules combining the functionalities of surface activity, polymerizability, and fluorescent properties within one molecule that could be seen as a fluorescent surfmer (surfactant and monomer) were successfully synthesized. A long hydrocarbon tail capped with a methacrylamide unit was anchored to a mono- or double-sutfonated Bodipy core. Time-resolved fluorescence measurements in aqueous solutions of the dyes enable one to trace the micelle formation and to find strong polarity dependence of fluorescence properties of the dyes. By using these molecules, polystyrene nanoparticles with fluorescent interfaces were synthesized via miniemulsion polymerization. The surfmers can be used alone or as surfactant additional to sodium dodecyl sulfate that provides stable emulsions and dispersions with a wide range (100-250 nm) of realizable particle sizes after polymerization. All synthesized nanoparticles showed bright fluorescence and can be easily investigated with conventional fluorescent confocal microscopy. Only the fluorescence of particles with double-sulfonated surfmer used is strongly sensitive to fluorescent quenchers as sodium iodide or methyl viologene dissolved in the continuous phase. In contrast, the fluorescence of nanoparticles labeled with the monosulfonated surfmer is only weakly quenched that might be explained by specific orientation of the Bodipy core at particle/water interface.

  DOI：

  10.1021/ma300090a

文献信息

• One-Pot Production of Fluorescent Surface-Labeled Polymeric Nanoparticles via Miniemulsion Polymerization with Bodipy Surfmers
  作者：Rüdiger Sauer、Andrey Turshatov、Stanislav Baluschev、Katharina Landfester

  DOI：10.1021/ma300090a

  日期：2012.5.8

  New molecules combining the functionalities of surface activity, polymerizability, and fluorescent properties within one molecule that could be seen as a fluorescent surfmer (surfactant and monomer) were successfully synthesized. A long hydrocarbon tail capped with a methacrylamide unit was anchored to a mono- or double-sutfonated Bodipy core. Time-resolved fluorescence measurements in aqueous solutions of the dyes enable one to trace the micelle formation and to find strong polarity dependence of fluorescence properties of the dyes. By using these molecules, polystyrene nanoparticles with fluorescent interfaces were synthesized via miniemulsion polymerization. The surfmers can be used alone or as surfactant additional to sodium dodecyl sulfate that provides stable emulsions and dispersions with a wide range (100-250 nm) of realizable particle sizes after polymerization. All synthesized nanoparticles showed bright fluorescence and can be easily investigated with conventional fluorescent confocal microscopy. Only the fluorescence of particles with double-sulfonated surfmer used is strongly sensitive to fluorescent quenchers as sodium iodide or methyl viologene dissolved in the continuous phase. In contrast, the fluorescence of nanoparticles labeled with the monosulfonated surfmer is only weakly quenched that might be explained by specific orientation of the Bodipy core at particle/water interface.