2,7-dibromo-9-(4-iodophenyl)-9H-carbazole | 568592-12-1

• 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: 2,7-dibromo-9-(4-iodophenyl)-9H-carbazole
• 英文别名: 2,7-Dibromo-9-(4-iodophenyl)carbazole
• CAS: 568592-12-1
• 化学式: C₁₈H₁₀Br₂IN
• 分子量: 526.997
• InChiKey: DGUIJPCZYPKNEP-UHFFFAOYSA-N

物化性质

• 沸点：
  551.1±50.0 °C(Predicted)
• 密度：
  2.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  22
• 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：

  2,7-dibromo-9-(4-iodophenyl)-9H-carbazole 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 正戊烷 为溶剂， 反应 66.5h， 生成 {4-[9-(4-ethynylphenyl)-7-(4-nitrophenylethynyl)-9H-carbazol-2-ylethynyl]phenyl}dimethylamine
  参考文献：
  名称：

  前往受表面约束电场驱动的分子电动机的途中。

  摘要：

  已经合成了四种可用作表面受电场驱动的分子电动机的菱形分子。菱形体由一对电子供体-受体臂和三脚架基座组成。分子臂基于具有强净偶极子的咔唑或低聚（亚苯基乙炔基）核。三脚架底座使用硅原子作为其核心。三脚架的支脚带有硫磺键合单元，作为乙酰基保护的苄硫醇，用于键合到金表面。自组装后，三脚架底座的几何形状允许菱形从金属表面向上突出。椭偏研究表明，自立构的自组装单分子层形成在Au表面上，分子表面的厚度与所需的竖轴布置相一致。因此，

  DOI：

  10.1021/jo034169h
• 作为产物：
  描述：

  对氟硝基苯 在 盐酸 、 potassium carbonate 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.83h， 生成 2,7-dibromo-9-(4-iodophenyl)-9H-carbazole
  参考文献：
  名称：

  前往受表面约束电场驱动的分子电动机的途中。

  摘要：

  已经合成了四种可用作表面受电场驱动的分子电动机的菱形分子。菱形体由一对电子供体-受体臂和三脚架基座组成。分子臂基于具有强净偶极子的咔唑或低聚（亚苯基乙炔基）核。三脚架底座使用硅原子作为其核心。三脚架的支脚带有硫磺键合单元，作为乙酰基保护的苄硫醇，用于键合到金表面。自组装后，三脚架底座的几何形状允许菱形从金属表面向上突出。椭偏研究表明，自立构的自组装单分子层形成在Au表面上，分子表面的厚度与所需的竖轴布置相一致。因此，

  DOI：

  10.1021/jo034169h

文献信息

• One-pot two-step synthesis of N-arylcarbazole-based skeleton
  作者：Sheng Tao、Ning Liu、Bin Dai

  DOI：10.1039/c5ra26698j

  日期：——

  A highly site-selective, one-pot, sequential C–N and C–C bond forming process was developed, affording a carbazole-based skeleton that contains biphenyl and diarylacetylene cores. The success of this process is attributed to the use of fluorinated iodoarenes as the starting material, the fluorine group of which preferentially reacts with carbazole. The subsequent coupling of the intermediate iodinated

  开发了一种高度位点选择性，一锅，顺序的C–N和C–C键形成工艺，从而提供了含有联苯和二芳基乙炔核心的咔唑骨架。该方法的成功归因于使用氟化碘代芳烃作为起始原料，其氟基团优先与咔唑反应。中间体碘代N-芳基咔唑与芳基硼酸或芳基乙炔的随后偶联产生所需产物。在不存在芳基硼酸或芳基乙炔的情况下，将中间体与过量的氟化碘代芳烃进行Pd催化的Ullmann偶联，从而在一锅法中得到Ullmann偶联产物。
• 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.
• Dopant-Free Hole-Transporting Polycarbazoles with Tailored Backbones for Efficient Inverted Perovskite Solar Cells
  作者：Yuanyuan Xie、Xuxian Wang、Qing Chen、Sizhou Liu、Yikai Yun、You Liu、Cheng Chen、Jungan Wang、Yezhou Cao、Fangfang Wang、Tianshi Qin、Wei Huang

  DOI：10.1021/acs.macromol.9b00372

  日期：2019.6.25

  Three conjugated polymers based on different linkage sites of carbazole repeat units, 3,6-PCzTPA, 2,7-PCzTPA, and 3,6-2,7-PCzTPA, were obtained through judicious molecular engineering. We observed that structure differences between 2,7- and 3,6-carbazole linkage sites could significantly influence intra- and intermolecular architectures and electronic states of materials. Herein, 3,6-PCzTPA and 3,6-2,7-PCzTPA with 3,6-carbazole units exhibited higher hole mobilities owing to the formation of radical cations, compared to 2,7-PCzTPA with 2,7-carbazole units. As a result, by using 3,6-2,7-PCzTPA as the hole-transporting material, perovskite solar cells with the p-i-n structure demonstrated the highest power conversion efficiency up to 18.4%. The outstanding device performance originated from compositive values of open-circuit voltage and fill factor, which were attributed to the suitable energy level as well as a high hole mobility of 3,6-2,7-PCzTPA. Moreover, its straightforward synthesis strategy, fine film-formation ability, and nondopant requirement indicated 3,6-2,7-PCzTPA as an ideal hole-transporting material for perovskite solar cells.