2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole | 1491114-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole
• 英文别名: 2-(Cyclohexen-1-yl)-1-phenylbenzimidazole
• CAS: 1491114-66-9
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: JGOFKCZXAGHRDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  iridium(III) chloride trihydrate 、 2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole 以 乙二醇乙醚 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Greenish yellow organic light emitting devices based on novel iridium complexes containing 2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole

  摘要：

  2-Cyclohexenyl-1-phenyl-1H-benzo[d]imidazole (Hcyclopbi) and its heterocyclometalated iridium complexes bis[2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole](acetylacetonate)iridium(III) [(cyclopbi)(2)Iracac] and bis[2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole][2-(3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridinate]iridium(III) [(cyclopbi)(2)IrCF3] were firstly designed and synthesized. Owing to the strong electron withdrawing ability of 2-(3-(trifluoromethyl)-1H-pyrazol) compared to that of acetylacetonate, blue shifted phosphorescence 542 nm was obtained for (cyclopbi)(2)IrCF3 compared to that of (cyclopbi)(2)Iracac 545 nm with photoluminescence quantum yields (phi) 0.22 and 0.25, respectively, as well the highest occupied molecular orbit (HOMO) energy level was estimated to be -5.10 eV for (cyclopbi)(2)IrCF3, 0.19 eV lower than that of -4.91 eV for (cyclopbi)(2)Iracac. When (cyclopbi)(2)Iracac was doped into 4,4'-bis(9H-carbazol-9-yl)biphenyl (CBP) as the emitting layer, high efficiency organic light emitting devices (OLEDs) were obtained with maximum current efficiency (eta(c)) 22.3 cd/A at 3.1 mA/cm(2) and maximum brightness 16,300 cd/m(2) at 171.6 mA/cm(2), which were comparable to those of bis(2-phenylpyridine)(acetylacetonate)iridium(III) [(ppy)(2)Iracac] with the same device structure. This results indicate that (cyclopbi)(2)Iracac and (cyclopbi)(2)IrCF3 are potential phosphorescent dyes used for OLEDs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.08.011
• 作为产物：
  描述：

  1-cyclohexene-1-carboxaldehyde 、 邻氨基二苯胺 以 乙二醇乙醚 为溶剂， 反应 24.0h， 以68.5%的产率得到2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  Greenish yellow organic light emitting devices based on novel iridium complexes containing 2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole

  摘要：

  2-Cyclohexenyl-1-phenyl-1H-benzo[d]imidazole (Hcyclopbi) and its heterocyclometalated iridium complexes bis[2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole](acetylacetonate)iridium(III) [(cyclopbi)(2)Iracac] and bis[2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole][2-(3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridinate]iridium(III) [(cyclopbi)(2)IrCF3] were firstly designed and synthesized. Owing to the strong electron withdrawing ability of 2-(3-(trifluoromethyl)-1H-pyrazol) compared to that of acetylacetonate, blue shifted phosphorescence 542 nm was obtained for (cyclopbi)(2)IrCF3 compared to that of (cyclopbi)(2)Iracac 545 nm with photoluminescence quantum yields (phi) 0.22 and 0.25, respectively, as well the highest occupied molecular orbit (HOMO) energy level was estimated to be -5.10 eV for (cyclopbi)(2)IrCF3, 0.19 eV lower than that of -4.91 eV for (cyclopbi)(2)Iracac. When (cyclopbi)(2)Iracac was doped into 4,4'-bis(9H-carbazol-9-yl)biphenyl (CBP) as the emitting layer, high efficiency organic light emitting devices (OLEDs) were obtained with maximum current efficiency (eta(c)) 22.3 cd/A at 3.1 mA/cm(2) and maximum brightness 16,300 cd/m(2) at 171.6 mA/cm(2), which were comparable to those of bis(2-phenylpyridine)(acetylacetonate)iridium(III) [(ppy)(2)Iracac] with the same device structure. This results indicate that (cyclopbi)(2)Iracac and (cyclopbi)(2)IrCF3 are potential phosphorescent dyes used for OLEDs. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.08.011