2,5-Dibromo-N,N'-bis-(4-octyl-phenyl)-benzene-1,4-diamine | 599575-85-6

• 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: 2,5-Dibromo-N,N'-bis-(4-octyl-phenyl)-benzene-1,4-diamine
• 英文别名: 2,5-dibromo-1-N,4-N-bis(4-octylphenyl)benzene-1,4-diamine
• CAS: 599575-85-6
• 化学式: C₃₄H₄₆Br₂N₂
• 分子量: 642.561
• InChiKey: ROLNVDPYVRZMAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  38
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,5-二溴-1,4-苯醌 、 4-辛基苯胺 在 四氯化钛 作用下， 以 氯苯 为溶剂， 反应 48.0h， 以82%的产率得到2,5-Dibromo-N,N'-bis-(4-octyl-phenyl)-benzene-1,4-diamine
  参考文献：
  名称：

  π-Conjugated Polymers Exhibiting a Novel Doping Based on Redox of Side Chains

  摘要：

  Novel polyphenylene and polythiophene derivatives that have N,N'-diphenyl-1,4-phenylene-diamine (PDA) units were synthesized using the palladium-catalyzed Suzuki coupling or cross coupling. Each obtained polymer has good redox activity, and the polyphenylene derivatives have two redox couples in acetonitrile that contain 1 M trifluoroacetric acid, whereas the polythiophene derivatives show only one redox couple under the same conditions. The electronic conductivity of the polythiophene derivatives was dramatically enhanced (0.1 S/cm) by the one-electron oxidation of the PDA unit (0.4 V, vs Ag/Ag+), because of the injection of a radical cation into the main chain from the PDA unit. Spectroelectrochemistry showed that the radical cation of the thiophene-substituted PDA was more delocalized than the phenylene-substituted unit. Electrochemical analysis of the model compounds revealed that the injection of radical monocation radical carriers into the main chain is based on electron communication between the intramolecular PDAs.

  DOI：

  10.1021/ma025833j

文献信息

• π-Conjugated Polymers Exhibiting a Novel Doping Based on Redox of Side Chains
  作者：Toyohiko Nishiumi、Masayoshi Higuchi、Kimihisa Yamamoto

  DOI：10.1021/ma025833j

  日期：2003.8.1

  Novel polyphenylene and polythiophene derivatives that have N,N'-diphenyl-1,4-phenylene-diamine (PDA) units were synthesized using the palladium-catalyzed Suzuki coupling or cross coupling. Each obtained polymer has good redox activity, and the polyphenylene derivatives have two redox couples in acetonitrile that contain 1 M trifluoroacetric acid, whereas the polythiophene derivatives show only one redox couple under the same conditions. The electronic conductivity of the polythiophene derivatives was dramatically enhanced (0.1 S/cm) by the one-electron oxidation of the PDA unit (0.4 V, vs Ag/Ag+), because of the injection of a radical cation into the main chain from the PDA unit. Spectroelectrochemistry showed that the radical cation of the thiophene-substituted PDA was more delocalized than the phenylene-substituted unit. Electrochemical analysis of the model compounds revealed that the injection of radical monocation radical carriers into the main chain is based on electron communication between the intramolecular PDAs.