3-bromo-9-(2-bromophenyl)-9H-carbazole | 1345415-06-6

• 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: 3-bromo-9-(2-bromophenyl)-9H-carbazole
• 英文别名: 3-Bromo-9-(2-bromophenyl)carbazole
• CAS: 1345415-06-6
• 化学式: C₁₈H₁₁Br₂N
• 分子量: 401.1
• InChiKey: JMJJPQFTJONHSY-UHFFFAOYSA-N

物化性质

• 熔点：
  190-194 °C
• 沸点：
  505.6±46.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-bromo-9-(2-bromophenyl)-9H-carbazole 在 四(三苯基膦)钯 、 allylchloro[1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidine]palladium(II) 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 、 水 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  一种有机化合物及其应用

  摘要：

  本发明公开了一种有机化合物及其应用，所述化合物的通式如下。所述化合物可应用于有机电致发光器件中，如空穴注入层材料、空穴传输层材料、电子阻隔层材料、发光层材料和覆盖层材料。与现有技术相比，本发明具有以下优点：(1)本发明所述有机化合物可用作空穴注入层材料、空穴传输层材料、电子阻隔层材料、绿色磷光或是红色荧光主体物质等发光层材料、覆盖层材料，从而应用于制备有机电致发光器件；(2)可降低驱动电压，提高发光效率、亮度、热稳定性、色彩纯度及器件的寿命；(3)采用本发明所述化合物制备获得的有机电致发光器件具有高效率及长寿命的优点。

  公开号：

  CN107663214B
• 作为产物：
  描述：

  N-(2-溴苯基)咔唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到3-bromo-9-(2-bromophenyl)-9H-carbazole
  参考文献：
  名称：

  Structure–property relationship in high triplet energy host materials with a phenylcarbazole core and diphenylphosphine oxide substituent

  摘要：

  A series of high triplet energy host materials with a carbazole core and a diphenylphosphine oxide substituent were synthesized and the effect of the substitution position on the photophysical properties and device performances of the host material was investigated. The substitution position of the diphenylphosphine oxide on the phenyl ring was changed and the substitution at ortho position of the phenyl ring induced the intramolecular charge transfer complex formation. The intramolecular charge transfer complex formation in the ortho substituted compound improved the current density. A maximum quantum efficiency of 20.4% was obtained in the phenylcarbazole host material with the phosphine oxide at para position of the phenyl group and the efficiency was degraded in the ortho substituted host. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2011.03.015

文献信息

• Site-Selective N-Arylation of Carbazoles with Halogenated Fluorobenzenes
  作者：Ning Liu、Bin Dai、Lei Wang、Enhui Ji

  DOI：10.1055/s-0035-1560386

  日期：——

  A method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles is described. The selectivity of iodine and fluorine atoms on the aromatic ring of fluorinated iodobenzenes was initially determined with a copper-N,N-diisopropylethylamine catalytic system. By changing the position of the iodine atom on the aromatic ring from the 3- or 4-position to the 2-position, the preferred coupling site was switched from the iodine atom to the fluorine atom. Steric hindrance of the fluorinated iodobenzenes is responsible for the selectivity switch. After elucidating the reaction mechanisms of these reaction processes, a metal-free method for the highly site-selective C-N bond-formation reaction of halogenated fluorobenzenes with carbazoles was revealed through C-F bond activation. The metal-free system is able to handle a range of halogenated groups. Thus, a broad range of chlorinated, brominated, and iodinated N-arylated carbazoles were generated, which are widely useful in organic chemistry.