N,N′-bis(2-ethylhexyl)-5H,12H-carbazolo[2,3-b]carbazole[6,7:13,14]tetracarboxylic acid diimide | 1423022-10-9

• 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,N′-bis(2-ethylhexyl)-5H,12H-carbazolo[2,3-b]carbazole[6,7:13,14]tetracarboxylic acid diimide
• 英文别名: N,N'-bis(2-ethylhexyl)-5H,12H-carbazolo[2,3-b]carbazole[6,7:13,14]bis(dicarboximide)；13,27-bis(2-ethylhexyl)-9,13,23,27-tetrazaoctacyclo[13.13.2.02,10.03,8.011,30.016,24.017,22.025,29]triaconta-1,3,5,7,10,15,17,19,21,24,29-undecaene-12,14,26,28-tetrone
• CAS: 1423022-10-9
• 化学式: C₄₂H₄₄N₄O₄
• 分子量: 668.836
• InChiKey: MJLZPPUJTKZNFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.73
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  106.34
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,6-二溴-N,N'-双(2-乙基己基)-1,8:4,5-萘四甲酰基二酰亚胺 、 2-溴苯胺 在 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 以10%的产率得到N,N′-bis(2-ethylhexyl)-5H,12H-carbazolo[2,3-b]carbazole[6,7:13,14]tetracarboxylic acid diimide
  参考文献：
  名称：

  Diindole-Annulated Naphthalene Diimides: Synthesis and Optical and Electronic Properties of Syn- and Anti-Isomers

  摘要：

  Here we report a selective method for the core-extension of naphthalene diimide (NDI) with two annulated indole rings leading to carbazolo[2,3-b]carbazole diimides (CbDIs) with exclusive syn-connectivity based on a regioselective nucleophilic substitution reaction of Br-4-NDI with arylamines, followed by palladium-catalyzed intramolecular C-C coupling. The oxygen analogues of anti-CbDIs, namely anti-benzofurobenzofuran diimides (anti-BfDIs), were obtained from 2,6-Br-2-NDI and 2-bromophenol. The syn- and anti-isomers of CbDIs were unambiguously characterized by single-crystal X-ray analysis. The optical properties of the present core-enlarged NDIs were studied, revealing clear differences in the absorption characteristics of the syn- and anti-isomers of CbDI, on one hand, and CbDI vs BfDI derivatives, on the other hand. Cyclic voltammetry studies showed that the redox properties are dependent on the substituents at the CbDI-core and oxygen atom containing BfDIs are more prone to reduction than the respective nitrogen analogues CbDIs. Vacuum-processed organic field effect transistors reveal CbDI and BfDI derivatives with n-channel, p-channel, as well as ambient transport characteristics with mobility values up to 0.2 cm(2)/(V s).

  DOI：

  10.1021/jo402365s

文献信息

• JP6080848
  申请人：——

  公开号：——

  公开（公告）日：——
• CARBAZOLOCARBAZOL-BIS(DICARBOXIMIDES) AND THEIR USE AS SEMICONDUCTORS
  申请人：BASF SE

  公开号：EP2742112B1

  公开（公告）日：2016-05-18
• US9583719B2
  申请人：——

  公开号：US9583719B2

  公开（公告）日：2017-02-28
• [EN] CARBAZOLOCARBAZOL-BIS(DICARBOXIMIDES) AND THEIR USE AS SEMICONDUCTORS<br/>[FR] CARBAZOLOCARBAZOL-BIS(DICARBOXIMIDES) ET LEUR UTILISATION EN TANT QUE SEMI-CONDUCTEURS
  申请人：BASF SE

  公开号：WO2013024409A1

  公开（公告）日：2013-02-21

  The present invention relates to carbazolocarbazol-bis(dicarboximides), a method for their preparation and their use as semiconductors, in particular as semiconductors in organic electronics and organic photovoltaics.