N-(1-heptyl-octyl)-N'-(hexyl-6'-azido)-perylene-3,4,9,10-tetracarboxylic acid bisimide | 1240321-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-(1-heptyl-octyl)-N'-(hexyl-6'-azido)-perylene-3,4,9,10-tetracarboxylic acid bisimide
• 英文别名: 7-(6-Azidohexyl)-18-pentadecan-8-yl-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone；7-(6-azidohexyl)-18-pentadecan-8-yl-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• CAS: 1240321-00-9
• 化学式: C₄₅H₅₁N₅O₄
• 分子量: 725.931
• InChiKey: QZOCQKQHDUBNGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  54
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丙烯酸丙炔酯 、 N-(1-heptyl-octyl)-N'-(hexyl-6'-azido)-perylene-3,4,9,10-tetracarboxylic acid bisimide 在 五甲基二乙烯三胺 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (1-(6-(1,3,8,10-tetraoxo-9-(pentadecan-8-yl)-3,8,9,10-tetrahydroanthra[2,1,9-def:6,5,10-d'e'f']diisoquinolin-2(1H)-yl)hexyl)-1H-1,2,3-triazol-4-yl)methyl acrylate
  参考文献：
  名称：

  NMRP versus “Click” Chemistry for the Synthesis of Semiconductor Polymers Carrying Pendant Perylene Bisimides

  摘要：

  The synthesis of well-defined polymers with pendant perylene bisimide (PBI) groups by a combination of nitroxide-mediated radical polymerization (NMRP) of trimethylsilyl propargyl acrylate followed by copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click" chemistry) is described. The kinetics of NMRP of trimethylsilyl propargyl acrylate polymerization was monitored by H-1 NMR and size exclusion chromatography (SEC). Almost quantitative conversion in the "click" reaction with an azide functionalized PBI derivative was proven by Fritz and H-1 NMR analysis. Thus, semiconductor polymers carrying PBI pendant groups with M-n up to 15800 g.mol(-1) and polydispersity indices as good as 1.16 were obtained by this route. These polymers were compared with poly(perylene bisimide acrylate)s, PPerAcr-(CH2)(11), and PPerAcr(CH2)(6), which were synthesized by direct NMRP of PBI acrylates. These samples do not carry any triazol unit and they differ in their spacer length connecting the PBI unit to the main chain. All polymers were comparatively studied by SEC, thermogravimetry, differential scanning calorimetry, polarization microscopy, UV/vis spectroscopy, and photoluminescence measurements. The crystalline structure of the polymers was analyzed by X-ray diffraction. Inductively coupled plasma mass spectrometry analysis confirmed that copper content in the "click" polymer could be reduced down to 126 ppm (w/w).

  DOI：

  10.1021/ma100708h
• 作为产物：
  描述：

  2-(6-溴己氧基)四氢吡喃 在 盐酸 、 二苯基膦叠氮化物 、 水 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 53.0h， 生成 N-(1-heptyl-octyl)-N'-(hexyl-6'-azido)-perylene-3,4,9,10-tetracarboxylic acid bisimide
  参考文献：
  名称：

  NMRP versus “Click” Chemistry for the Synthesis of Semiconductor Polymers Carrying Pendant Perylene Bisimides

  摘要：

  The synthesis of well-defined polymers with pendant perylene bisimide (PBI) groups by a combination of nitroxide-mediated radical polymerization (NMRP) of trimethylsilyl propargyl acrylate followed by copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click" chemistry) is described. The kinetics of NMRP of trimethylsilyl propargyl acrylate polymerization was monitored by H-1 NMR and size exclusion chromatography (SEC). Almost quantitative conversion in the "click" reaction with an azide functionalized PBI derivative was proven by Fritz and H-1 NMR analysis. Thus, semiconductor polymers carrying PBI pendant groups with M-n up to 15800 g.mol(-1) and polydispersity indices as good as 1.16 were obtained by this route. These polymers were compared with poly(perylene bisimide acrylate)s, PPerAcr-(CH2)(11), and PPerAcr(CH2)(6), which were synthesized by direct NMRP of PBI acrylates. These samples do not carry any triazol unit and they differ in their spacer length connecting the PBI unit to the main chain. All polymers were comparatively studied by SEC, thermogravimetry, differential scanning calorimetry, polarization microscopy, UV/vis spectroscopy, and photoluminescence measurements. The crystalline structure of the polymers was analyzed by X-ray diffraction. Inductively coupled plasma mass spectrometry analysis confirmed that copper content in the "click" polymer could be reduced down to 126 ppm (w/w).

  DOI：

  10.1021/ma100708h

文献信息

• NMRP versus “Click” Chemistry for the Synthesis of Semiconductor Polymers Carrying Pendant Perylene Bisimides
  作者：Andreas S. Lang、Anne Neubig、Michael Sommer、Mukundan Thelakkat

  DOI：10.1021/ma100708h

  日期：2010.9.14

  The synthesis of well-defined polymers with pendant perylene bisimide (PBI) groups by a combination of nitroxide-mediated radical polymerization (NMRP) of trimethylsilyl propargyl acrylate followed by copper-catalyzed azide-alkyne cycloaddition (CuAAC, "click" chemistry) is described. The kinetics of NMRP of trimethylsilyl propargyl acrylate polymerization was monitored by H-1 NMR and size exclusion chromatography (SEC). Almost quantitative conversion in the "click" reaction with an azide functionalized PBI derivative was proven by Fritz and H-1 NMR analysis. Thus, semiconductor polymers carrying PBI pendant groups with M-n up to 15800 g.mol(-1) and polydispersity indices as good as 1.16 were obtained by this route. These polymers were compared with poly(perylene bisimide acrylate)s, PPerAcr-(CH2)(11), and PPerAcr(CH2)(6), which were synthesized by direct NMRP of PBI acrylates. These samples do not carry any triazol unit and they differ in their spacer length connecting the PBI unit to the main chain. All polymers were comparatively studied by SEC, thermogravimetry, differential scanning calorimetry, polarization microscopy, UV/vis spectroscopy, and photoluminescence measurements. The crystalline structure of the polymers was analyzed by X-ray diffraction. Inductively coupled plasma mass spectrometry analysis confirmed that copper content in the "click" polymer could be reduced down to 126 ppm (w/w).