3,9-二溴-5,11-二辛基-5,11-二氢吲哚[3,2-b]咔唑 | 951307-27-0

• 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: 3,9-二溴-5,11-二辛基-5,11-二氢吲哚[3,2-b]咔唑
• 英文名称: 3,9-dibromo-5,11-dioctylindolo[3,2-b]carbazole
• 英文别名: 3,9-Dibromo-5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole
• CAS: 951307-27-0
• 化学式: C₃₄H₄₂Br₂N₂
• 分子量: 638.529
• InChiKey: HFMSSMCMAMHDMB-UHFFFAOYSA-N

物化性质

• 沸点：
  708.4±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,9-二溴-5,11-二辛基-5,11-二氢吲哚[3,2-b]咔唑 、 N,N-二苯基-4-乙烯基苯胺 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以52%的产率得到4,4'-((5,11-dioctyl-5,11-dihydroindolo[3,2-b]carbazole-3,9-diyl)bis(ethene-2,1-diyl))bis(N,N-diphenylaniline)
  参考文献：
  名称：

  TPA-active D–π–D fluorophores with rigid, planar cores from phenylene to indenofluorene and indolocarbazole

  摘要：

  A series of D-pi-D quadrupolar fluorophores with systematically varied pi-conjugated cores were prepared using the Heck reaction and their single- and two-photon photophysical properties were examined. Introduction of extended pi-conjugated cores such as indenofluorene/indolocarbazole was found to induce only small shifts in the absorption and emission maxima versus the phenylene linked fluorophore but greatly enhance their single- and two-photon absorption cross-sections. The effects of positional substitution oil the properties of the indolocarbazole derivatives were also investigated. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2009.11.009
• 作为产物：
  描述：

  3,9-dibromo-5,11-dihydroindolo[3,2-b]carbazole 、 1-溴辛烷 在 四丁基溴化铵 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 5.0h， 以97%的产率得到3,9-二溴-5,11-二辛基-5,11-二氢吲哚[3,2-b]咔唑
  参考文献：
  名称：

  Indolo[3,2-b]carbazole and benzofurazan based narrow band-gap polymers for photovoltaic cells

  摘要：

  两种基于吲哚并[3,2-b]咔唑和5,6-双(辛氧基)苯并呋喃的窄带隙聚合物PICzODTBF和PICzHDDTBF，分别具有最大的转换效率为3.32%和3.13%，其开路电压分别为0.80 V和0.95 V。

  DOI：

  10.1039/c4nj00705k

文献信息

• Synthesis, Characterization, and Application of Indolo[3,2-<i>b</i>]carbazole Semiconductors
  作者：Pierre-Luc T. Boudreault、Salem Wakim、Nicolas Blouin、Michel Simard、Christian Tessier、Ye Tao、Mario Leclerc

  DOI：10.1021/ja071923y

  日期：2007.7.1

  The synthesis, characterization, and field-effect transistor (FET) properties of new indolo[3,2-b]carbazoles are described. In particular, an extensive characterization of their crystal structures has revealed the importance of the nature of the side chains (alkyl, phenyl, thienyl substituents) on their solid-state organization. These organic materials have exhibited p-type FET behavior with hole mobilities

  描述了新型吲哚 [3,2-b] 咔唑的合成、表征和场效应晶体管 (FET) 特性。特别是，对其晶体结构的广泛表征揭示了侧链（烷基、苯基、噻吩基取代基）的性质对其固态组织的重要性。这些有机材料表现出 p 型 FET 行为，空穴迁移率高达 0.2 cm2 V(-1) s(-1)，开/关电流比高于 10(6)。使用苯基取代的吲哚并[3,2-b]咔唑获得了最好的结果，因为苯基取代基的存在似乎允许低聚分子之间有效重叠。更重要的是，FET 特性在空气中的几个月内保持不变。
• TPA-active D–π–D fluorophores with rigid, planar cores from phenylene to indenofluorene and indolocarbazole
  作者：Zhiqiang Liu、Duxia Cao、Ying Chen、Qi Fang

  DOI：10.1016/j.dyepig.2009.11.009

  日期：2010.6

  A series of D-pi-D quadrupolar fluorophores with systematically varied pi-conjugated cores were prepared using the Heck reaction and their single- and two-photon photophysical properties were examined. Introduction of extended pi-conjugated cores such as indenofluorene/indolocarbazole was found to induce only small shifts in the absorption and emission maxima versus the phenylene linked fluorophore but greatly enhance their single- and two-photon absorption cross-sections. The effects of positional substitution oil the properties of the indolocarbazole derivatives were also investigated. (C) 2009 Elsevier Ltd. All rights reserved.
• Indolo[3,2-b]carbazole and benzofurazan based narrow band-gap polymers for photovoltaic cells
  作者：Bin Zhang、Lei Yu、Li Fan、Na Wang、Liwen Hu、Wei Yang

  DOI：10.1039/c4nj00705k

  日期：——

  Two indolo[3,2-b]carbazole and 5,6-bis(octyloxy)benzofurazan based narrow band-gap polymersPICzODTBFandPICzHDDTBFgive maximum power conversion efficiencies of 3.32% and 3.13% with open circuit voltages of 0.80 V and 0.95 V, respectively.

  两种基于吲哚并[3,2-b]咔唑和5,6-双(辛氧基)苯并呋喃的窄带隙聚合物PICzODTBF和PICzHDDTBF，分别具有最大的转换效率为3.32%和3.13%，其开路电压分别为0.80 V和0.95 V。