5-bromo-2-(pyridin-2-yl)-1H-isoindole-1,3(2H)-dione | 342777-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-bromo-2-(pyridin-2-yl)-1H-isoindole-1,3(2H)-dione
• 英文别名: 5-Bromo-2-pyridin-2-ylisoindole-1,3-dione
• CAS: 342777-68-8
• 化学式: C₁₃H₇BrN₂O₂
• 分子量: 303.115
• InChiKey: WSEFGFBZMGMEAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(pyridin-2-yl)-1H-isoindole-1,3(2H)-dione 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 70.0h， 生成 5-{(E)=2-[4-((E)-2{1,3-dioxo-3-[3-(triethoxysilyl)propyl]-2,3-dihydro-1H-isoindol-5-yl}vinyl)-2,5-bis(octyloxy)phenyl]vinyl}-2-[3-(triethoxysilyl)propyl]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Nanostructuration of Phenylenevinylenediimide-Bridged Silsesquioxane:  From Electroluminescent Molecular J-Aggregates to Photoresponsive Polymeric H-Aggregates

  摘要：

  A new approach to control molecular aggregation of pi-conjugated chromophores in the solid state has been investigated. Our strategy was to use a modifiable bulky fragment which should induce a J-aggregation and offer the possibility to reach an H-aggregation upon its chemical modification by lateral slip of T-conjugated molecules. The chosen fragment for that purpose was the hydrolyzable triethoxysilane function (Si(OEt)(3)). Our objective was to design and synthesize electroluminescent or solar cell hybrid organic-inorganic materials by the sol-gel process applied to a bifunctionalized silane. With this intention, the synthesis of the sol-gel processable phenylenevinylenediimide silsesquioxane 6 was accomplished and the study of spin-coated thin films of the pure silane precursor subjected or not to the sol-gel process has been carried out. Optical properties of 6 are consistent with the formation of J-aggregates in the solid state due to the steric hindrance introduced by the triethoxysilane units. Conversely, the spectroscopic behavior observed for the hybrid film 6F is attributed to an H-aggregation corresponding to a "card pack" orientation of the distyrylbenzeneimide chromophores in the compressed silicate network. Morevover, 6 and 6F also exhibited different electronic behaviors: light-emitting diodes exhibited high brightness with the native precursor 6 and almost no light output with the sol-gel processed silsesquioxane 6F. Photovoltaic cells showed the opposite behavior with low photocurrent generation in the precursor case and higher photocurrents with the sol-gel processed layers. These results provide a deeper understanding of the present self-assembly process that is strongly governed by the molecular packing of the oligosiloxane precursor.

  DOI：

  10.1021/ja058680z
• 作为产物：
  描述：

  2-氨基吡啶 、 4-溴邻苯二甲酸酐 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以75%的产率得到5-bromo-2-(pyridin-2-yl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Nanostructuration of Phenylenevinylenediimide-Bridged Silsesquioxane:  From Electroluminescent Molecular J-Aggregates to Photoresponsive Polymeric H-Aggregates

  摘要：

  A new approach to control molecular aggregation of pi-conjugated chromophores in the solid state has been investigated. Our strategy was to use a modifiable bulky fragment which should induce a J-aggregation and offer the possibility to reach an H-aggregation upon its chemical modification by lateral slip of T-conjugated molecules. The chosen fragment for that purpose was the hydrolyzable triethoxysilane function (Si(OEt)(3)). Our objective was to design and synthesize electroluminescent or solar cell hybrid organic-inorganic materials by the sol-gel process applied to a bifunctionalized silane. With this intention, the synthesis of the sol-gel processable phenylenevinylenediimide silsesquioxane 6 was accomplished and the study of spin-coated thin films of the pure silane precursor subjected or not to the sol-gel process has been carried out. Optical properties of 6 are consistent with the formation of J-aggregates in the solid state due to the steric hindrance introduced by the triethoxysilane units. Conversely, the spectroscopic behavior observed for the hybrid film 6F is attributed to an H-aggregation corresponding to a "card pack" orientation of the distyrylbenzeneimide chromophores in the compressed silicate network. Morevover, 6 and 6F also exhibited different electronic behaviors: light-emitting diodes exhibited high brightness with the native precursor 6 and almost no light output with the sol-gel processed silsesquioxane 6F. Photovoltaic cells showed the opposite behavior with low photocurrent generation in the precursor case and higher photocurrents with the sol-gel processed layers. These results provide a deeper understanding of the present self-assembly process that is strongly governed by the molecular packing of the oligosiloxane precursor.

  DOI：

  10.1021/ja058680z

文献信息

• Nanostructuration of Phenylenevinylenediimide-Bridged Silsesquioxane:  From Electroluminescent Molecular J-Aggregates to Photoresponsive Polymeric H-Aggregates
  作者：Olivier J. Dautel、Guillaume Wantz、Robert Almairac、David Flot、Lionel Hirsch、Jean-Pierre Lere-Porte、Jean-Paul Parneix、Françoise Serein-Spirau、Laurence Vignau、Joël J. E. Moreau

  DOI：10.1021/ja058680z

  日期：2006.4.1

  A new approach to control molecular aggregation of pi-conjugated chromophores in the solid state has been investigated. Our strategy was to use a modifiable bulky fragment which should induce a J-aggregation and offer the possibility to reach an H-aggregation upon its chemical modification by lateral slip of T-conjugated molecules. The chosen fragment for that purpose was the hydrolyzable triethoxysilane function (Si(OEt)(3)). Our objective was to design and synthesize electroluminescent or solar cell hybrid organic-inorganic materials by the sol-gel process applied to a bifunctionalized silane. With this intention, the synthesis of the sol-gel processable phenylenevinylenediimide silsesquioxane 6 was accomplished and the study of spin-coated thin films of the pure silane precursor subjected or not to the sol-gel process has been carried out. Optical properties of 6 are consistent with the formation of J-aggregates in the solid state due to the steric hindrance introduced by the triethoxysilane units. Conversely, the spectroscopic behavior observed for the hybrid film 6F is attributed to an H-aggregation corresponding to a "card pack" orientation of the distyrylbenzeneimide chromophores in the compressed silicate network. Morevover, 6 and 6F also exhibited different electronic behaviors: light-emitting diodes exhibited high brightness with the native precursor 6 and almost no light output with the sol-gel processed silsesquioxane 6F. Photovoltaic cells showed the opposite behavior with low photocurrent generation in the precursor case and higher photocurrents with the sol-gel processed layers. These results provide a deeper understanding of the present self-assembly process that is strongly governed by the molecular packing of the oligosiloxane precursor.