N,N′-bis(2′,6′-diisopropylphenyl)-2,7-dibromo-3,6-diphenylamino-1,4,5,8-naphthalenetetracarboxylic acid diimide | 1498354-62-3

• 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: N,N′-bis(2′,6′-diisopropylphenyl)-2,7-dibromo-3,6-diphenylamino-1,4,5,8-naphthalenetetracarboxylic acid diimide
• 英文别名: 2,10-Dianilino-3,9-dibromo-6,13-bis[2,6-di(propan-2-yl)phenyl]-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8,10,15-pentaene-5,7,12,14-tetrone
• CAS: 1498354-62-3
• 化学式: C₅₀H₄₆Br₂N₄O₄
• 分子量: 926.748
• InChiKey: SUSPSCMDPJRUPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.3
• 重原子数：
  60
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N′-bis(2′,6′-diisopropylphenyl)-2,7-dibromo-3,6-diphenylamino-1,4,5,8-naphthalenetetracarboxylic acid diimide 在 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以33%的产率得到N,N′-bis(2,6-diisopropylphenyl)-5H,8H-carbazolo[2,3-b]carbazole[6,7:13,14]tetracarboxylic acid diimide
  参考文献：
  名称：

  파이-연장된 나프탈렌 디이미드의 제조 및 반도체로서의 그의 용도

  摘要：

  本发明提供了化学式为1或2的化合物以及包含这些化合物的电子装置。

  公开号：

  KR20150142043A
• 作为产物：
  描述：

  4,5,9,10-四溴-2,7-二(2,6-二异丙苯基)苯并[LMN][3,8]邻菲罗啉-1,3,6,8(2H,7H)-四酮 、 苯胺 以 氯仿 为溶剂， 反应 0.67h， 以82%的产率得到N,N′-bis(2′,6′-diisopropylphenyl)-2,7-dibromo-3,6-diphenylamino-1,4,5,8-naphthalenetetracarboxylic acid diimide
  参考文献：
  名称：

  파이-연장된 나프탈렌 디이미드의 제조 및 반도체로서의 그의 용도

  摘要：

  本发明提供了化学式为1或2的化合物以及包含这些化合物的电子装置。

  公开号：

  KR20150142043A

文献信息

• Diindole-Annulated Naphthalene Diimides: Synthesis and Optical and Electronic Properties of <i>Syn</i>- and <i>Anti</i>-Isomers
  作者：Sabin-Lucian Suraru、Christian Burschka、Frank Würthner

  DOI：10.1021/jo402365s

  日期：2014.1.3

  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).
• PREPARATION OF PI-EXTENDED NAPHTHALENE DIIMIDES AND THEIR USE AS SEMICONDUCTOR
  申请人：BASF SE

  公开号：EP2989109B1

  公开（公告）日：2019-09-11
• US9444058B2
  申请人：——

  公开号：US9444058B2

  公开（公告）日：2016-09-13
• [EN] PREPARATION OF PI-EXTENDED NAPHTHALENE DIIMIDES AND THEIR USE AS SEMICONDUCTOR<br/>[FR] PRÉPARATION DE NAPHTHALENE DIIMIDES À EXTENSION PI ET LEUR UTLISATION EN TANT QUE SEMI-CONDUCTEUR
  申请人：BASF SE

  公开号：WO2014174435A2

  公开（公告）日：2014-10-30

  The present invention provides the compounds of formulae (1) or (2) and electronic devices comprising these compounds.