2,6-dibromonaphthalene-1,4,5,8-tetracarboxylic acid n-octyl ester | 1498354-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-dibromonaphthalene-1,4,5,8-tetracarboxylic acid n-octyl ester
• CAS: 1498354-97-4
• 化学式: C₄₆H₇₀Br₂O₈
• 分子量: 910.865
• InChiKey: WHEWEGPPHJELLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.43
• 重原子数：
  56.0
• 可旋转键数：
  32.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,6-dibromonaphthalene-1,4,5,8-tetracarboxylic acid n-octyl ester 、 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 0.67h， 以13%的产率得到tetraoctyl 5,12-dihydrocarbazolo[3,2-b]carbazole-6,7,13,14-tetracarboxylate
  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
• 作为产物：
  描述：

  1-溴辛烷 、 2,6-二溴萘-1,4,5,8-四羧酸二酐 在 potassium hydroxide 、 四正辛基溴化铵 作用下， 以 水 为溶剂， 反应 3.0h， 以36%的产率得到2,6-dibromonaphthalene-1,4,5,8-tetracarboxylic acid n-octyl ester
  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