3,10-dichloro-5,8-dihydro-14-octyl-diindolo[3,2-b:2',3'-h]carbazole | 778649-46-0

• 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: 3,10-dichloro-5,8-dihydro-14-octyl-diindolo[3,2-b:2',3'-h]carbazole
• 英文别名: 8,22-Dichloro-15-octyl-5,15,25-triazaheptacyclo[14.11.0.02,14.04,12.06,11.018,26.019,24]heptacosa-1(27),2,4(12),6(11),7,9,13,16,18(26),19(24),20,22-dodecaene
• CAS: 778649-46-0
• 化学式: C₃₂H₂₉Cl₂N₃
• 分子量: 526.508
• InChiKey: KNTDBEOYUGOLJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.5
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,10-dichloro-5,8-dihydro-14-octyl-diindolo[3,2-b:2',3'-h]carbazole 、 1-溴辛烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 以96%的产率得到3,10-dichloro-5,8,14-trioctyl-diindolo[3,2-b:2',3'-h]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：

  N-octyl-3,6-dibromo-2,7-bis(4'-chloro-2'-nitrophenyl)carbazole 在 铜 copper(l) iodide 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 乙醇 、 二丁醚 、 乙酸乙酯 为溶剂， 反应 84.0h， 生成 3,10-dichloro-5,8-dihydro-14-octyl-diindolo[3,2-b:2',3'-h]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

文献信息

• 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.