3-溴-9-(3-溴苯基)咔唑 | 1345415-05-5

• 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
• 中文名称: 3-溴-9-(3-溴苯基)咔唑
• 英文名称: 3-bromo-9-(3-bromophenyl)-9H-carbazole
• 英文别名: 3-Bromo-9-(3-bromophenyl)carbazole
• CAS: 1345415-05-5
• 化学式: C₁₈H₁₁Br₂N
• 分子量: 401.1
• InChiKey: MDTBMIJVCSGPQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  187 °C
• 沸点：
  506.4±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-溴-9-(3-溴苯基)咔唑 在 正丁基锂 、 双氧水 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-(diphenylphosphoryl)-9-(3-(diphenylphosphoryl)phenyl)-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
• 作为产物：
  描述：

  1-溴-3-碘苯 在 N-溴代丁二酰亚胺(NBS) 、 二苯并-18-冠醚-6 、 铜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 3-溴-9-(3-溴苯基)咔唑
  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

• Copper/β-diketone-catalysed N-arylation of carbazoles
  作者：Fei Chen、Ning Liu、Enhui Ji、Bin Dai

  DOI：10.1039/c5ra07690k

  日期：——

  A copper/β-diketone-catalysedN-arylation of carbazoles with aryl iodides is developed with broad substrate applicability and moderate to good yields.

  使用铜/β-二酮催化剂对碳酰胺与芳基碘化物进行N-芳基化反应，具有广泛的底物适用性和中等至良好的产率。
• 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.
• CARBAZOLE MIT ZWEI DIBENZOFURAN- ODER DIBENZOTHIOPHENSUBSTITUENTEN
  申请人：Merck Patent GmbH

  公开号：EP3237409B1

  公开（公告）日：2022-01-05
• CARBAZOLES WITH TWO DIBENZOFURAN OR DIBENZOTHIOPHENE SUBSTITUENTS
  申请人：Merck Patent GmbH

  公开号：US20190044071A1

  公开（公告）日：2019-02-07

  The present invention relates to carbazoles having two dibenzofuran or dibenzothiophene substituents, and to electronic devices, especially organic electroluminescent devices, comprising these compounds.