N-octyl-2,7-bis(2'-nitrophenyl)carbazole | 755758-66-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-octyl-2,7-bis(2'-nitrophenyl)carbazole
• 英文别名: 2,7-Bis(2-nitrophenyl)-9-octyl-9H-carbazole；2,7-bis(2-nitrophenyl)-9-octylcarbazole
• CAS: 755758-66-8
• 化学式: C₃₂H₃₁N₃O₄
• 分子量: 521.616
• InChiKey: HWEKCFJZIIXCNF-UHFFFAOYSA-N

物化性质

• 熔点：
  120-121 °C(Solv: methanol (67-56-1))
• 沸点：
  658.2±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  96.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-octyl-2,7-bis(2'-nitrophenyl)carbazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 丙酮 为溶剂， 以86%的产率得到N-octyl-3,6-dibromo-2,7-bis(2'-nitrophenyl)carbazole
  参考文献：
  名称：

  Synthesis of Diindolocarbazoles by Ullmann Reaction:  A Rapid Route to Ladder Oligo(p-aniline)s

  摘要：

  New and facile synthesis of symmetric diindolocarbazoles was developed using the copper-catalyzed Ullmann reaction. The key step is a double-intramolecular cyclization reaction realized on N-alkyl-3,6-dibromo-2,7-bis(2'aminophenyl)carbazole derivatives which offers the desired symmetric ladder oligo(p-aniline)s. Depending upon the nature of the side- and/or end-groups, well-defined thin films and/or semiladder polymers could be obtained. These electroactive ladder oligomers may have great potential in organic electronics.

  DOI：

  10.1021/ol048543r
• 作为产物：
  描述：

  9-辛基-2,7-双(4,4,5,5-四甲基-1,3,2-二噁硼烷-2-基)-9h-咔唑 、 1-溴-2-硝基苯 在 palladium diacetate potassium carbonate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以84%的产率得到N-octyl-2,7-bis(2'-nitrophenyl)carbazole
  参考文献：
  名称：

  Synthesis of Diindolocarbazoles by Cadogan Reaction:  Route to Ladder Oligo(p-aniline)s

  摘要：

  Symmetric and nonsymmetric diindolocarbazoles were successfully synthesized for the first time by a Cadogan ring closure using N-alkyl-2,7-disubstituted carbazole precursors. Cyclization reaction on N-alkyl-2,7-di(2'-nitrophenyl) carbazole derivatives is not regioselective and produced a separable mixture of symmetric and nonsymmetric diindolocarbazoles. A carbazole derivative with methyl protective groups at the 1- and 8-positions was therefore used to obtain a symmetric ladder oligo-(p-aniline) (compound 22). Optical and electrochemical properties of compound 22 indicate that its neutral semiconducting form is stable in air. This novel class of electroactive ladder oligomers should create new opportunities in micro- and nanoelectronics.

  DOI：

  10.1021/jo049419o

文献信息

• Synthesis of Diindolocarbazoles by Cadogan Reaction:  Route to Ladder Oligo(<i>p</i>-aniline)s
  作者：Jimmy Bouchard、Salem Wakim、Mario Leclerc

  DOI：10.1021/jo049419o

  日期：2004.8.1

  Symmetric and nonsymmetric diindolocarbazoles were successfully synthesized for the first time by a Cadogan ring closure using N-alkyl-2,7-disubstituted carbazole precursors. Cyclization reaction on N-alkyl-2,7-di(2'-nitrophenyl) carbazole derivatives is not regioselective and produced a separable mixture of symmetric and nonsymmetric diindolocarbazoles. A carbazole derivative with methyl protective groups at the 1- and 8-positions was therefore used to obtain a symmetric ladder oligo-(p-aniline) (compound 22). Optical and electrochemical properties of compound 22 indicate that its neutral semiconducting form is stable in air. This novel class of electroactive ladder oligomers should create new opportunities in micro- and nanoelectronics.
• Synthesis of Diindolocarbazoles by Ullmann Reaction:  A Rapid Route to Ladder Oligo(<i>p</i>-aniline)s
  作者：Salem Wakim、Jimmy Bouchard、Nicolas Blouin、Alexandre Michaud、Mario Leclerc

  DOI：10.1021/ol048543r

  日期：2004.9.1

  New and facile synthesis of symmetric diindolocarbazoles was developed using the copper-catalyzed Ullmann reaction. The key step is a double-intramolecular cyclization reaction realized on N-alkyl-3,6-dibromo-2,7-bis(2'aminophenyl)carbazole derivatives which offers the desired symmetric ladder oligo(p-aniline)s. Depending upon the nature of the side- and/or end-groups, well-defined thin films and/or semiladder polymers could be obtained. These electroactive ladder oligomers may have great potential in organic electronics.