7-bromo-2-carbazole-9,9-bis-n-hexylfluoerene | 921211-03-2

• 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: 7-bromo-2-carbazole-9,9-bis-n-hexylfluoerene
• 英文别名: 2-bromo-7-(carbazol-9-yl)-9,9-bis-n-hexylfluorene；9-(7-bromo-9,9-dihexyl-9H-fluoren-2-yl)-9H-carbazole；2-bromo-7-(9H-carbazol-9-yl)-9,9-dihexylfluorene；9-(7-Bromo-9,9-dihexylfluoren-2-yl)carbazole
• CAS: 921211-03-2
• 化学式: C₃₇H₄₀BrN
• 分子量: 578.635
• InChiKey: XISNCLRKAHNQJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  7-bromo-2-carbazole-9,9-bis-n-hexylfluoerene 在 四(三苯基膦)钯 、 1,1'-bipyridyl N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 、 三苯基膦 、 nickel dichloride 、 锌 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基乙酰胺 、 溶剂黄146 为溶剂， 反应 43.0h， 生成 5,5'-bis[2-(carbazol-9-yl)-9,9-bis-n-hexylfluoren-7-yl]-2,2'-bithiophene
  参考文献：
  名称：

  Synthesis and characterization of N-carbazole end-capped oligofluorene-thiophenes

  摘要：

  A series of novel N-carbazole end-capped oligofluorene-thiophenes with one, two, three, and four thiophene rings were synthesized using either palladium catalyzed cross-coupling reaction or nickel-catalyzed reductive dimerization. All the oligomers have been characterized by H-1, C-13 NMR, FTIR, UV-vis, PL spectroscopy and mass spectrometry. It has been demonstrated that the optical, thermal, and electrochemical properties of these materials can be tuned by varying the conjugation length of the oligothiophene segment. The terminal carbazole and fluorene moieties of the resulting materials are beneficial for their morphology, conjugation length, and solubility. These bright fluorescent, thermally and electrochemically stable compounds have potential applications as light-emitting and hole-transporting layers in organic light-emitting devices. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.017
• 作为产物：
  描述：

  2-溴-7-碘芴 在 copper(l) iodide 、 1,10-菲罗啉 、 四丁基氯化铵 、 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 7-bromo-2-carbazole-9,9-bis-n-hexylfluoerene
  参考文献：
  名称：

  Colour tuning of blue electroluminescence using bipolar carbazole–oxadiazole molecules in single-active-layer organic light emitting devices (OLEDs)

  摘要：

  在一系列新的双极性咔唑-2,5-二芳基-1,3,4-恶二唑杂化分子 1-7 中，采用了一种综合通用策略来调节发光颜色。报告了它们的合成、溶液吸收和发射特性以及循环伏安数据。使用 DFT（密度泛函理论）的计算表明它们具有有利于双极电荷传输的分子轨道。单活性层有机发光器件 (OLED) 是通过热蒸发法使用双极性化合物作为 ITO:PEDOT-PSS:X:Ca/Al (X = 1-7) 结构中的发射极来制造的。该系列化合物的结构与性能关系的评估重点是 OLED 性能和发射颜色。 HOMO-LUMO 间隙通过 1-7 分子亚基的系统修饰而变化，从而使电致发光的颜色从深蓝色 (CIE x,y 0.157, 0.079) 调整到绿色 (CIE x, y 0.151, 0.096)。由于分子的良好加工性、双极结构、颜色可调性以及使用简单器件架构的 OLED 的高效性能，这些材料对于进一步开发非常有吸引力。

  DOI：

  10.1039/c2jm31825c

文献信息

• Synthesis and characterization of N-carbazole end-capped oligofluorenes
  作者：Vinich Promarak、Sayant Saengsuwan、Siriporn Jungsuttiwong、Taweesak Sudyoadsuk、Tinnagon Keawin

  DOI：10.1016/j.tetlet.2006.11.007

  日期：2007.1

  A series of N-carbazole end-capped oligofluorenes (CFn, n = 1–3) were synthesized. The 9-position of the carbazole moiety was attached to the terminal ends of the oligofluorene cores using an Ullmann coupling reaction. These molecules exhibit red shifts in absorption and photoluminescence spectra with respect to the number of fluorene units and excellent electrochemical reversibility. They were found

  合成了一系列N-咔唑封端的低聚芴（CF n，n = 1-3）。使用Ullmann偶联反应，将咔唑部分的9位连接至低聚芴核的末端。这些分子相对于芴单元的数量在吸收光谱和光致发光光谱中表现出红移，并具有出色的电化学可逆性。发现它们是用于有机发光二极管（OLED）的潜在的蓝色发光或空穴传输材料。
• Polymer and organic light emitting device including polymer
  申请人：Yang Hye-yeon

  公开号：US08558007B2

  公开（公告）日：2013-10-15

  A polymer and an organic light-emitting device including the polymer are provided, wherein the polymer comprises a polymeric unit represented by the Formula: In which variables are as defined herein.

  提供了一种聚合物和包括该聚合物的有机发光器件，其中该聚合物包括由以下式表示的聚合单元：其中变量如本文所定义。
• Oligofluorene-based push–pull type functional materials for blue light-emitting diodes
  作者：Ying Lin、Yu Chen、Teng-Ling Ye、Zhi-Kuan Chen、Yan-Feng Dai、Dong-Ge Ma

  DOI：10.1016/j.jphotochem.2011.12.008

  日期：2012.2

  2″-ter(9,9-dihexylfluorene) (F3), and 7-(9H-carbazole-9-yl)-7″′-(4-cyanophenyl)-2,2′:7′,2″:7″,2″′-quarter(9,9-dihexylfluorene) (F4) were synthesized and characterized. Their onset decomposition temperatures for the thermal bond cleavage and the glass-transition temperatures were in general increased with increasing number of fluorene units. In dilute toluene solution, the oligofluorenes exhibited main

  一系列新型的低聚芴基推挽式蓝色发光功能材料，即2-（9 H-咔唑-9-基）-7-（4-氰基苯基）-9,9-二己基芴（F1）， 7-（9 H-咔唑-9-基）-7'-（4-氰基苯基）-2,2'-双（9,9-二己基芴）（F2），7-（9 H-咔唑-9-基）-7“-（4-氰基苯基）-2,2'：7'，2” -ter（9,9-二己基芴）（F3）和7-（9 H-咔唑-9-基）-7“ ′-（4-氰基苯基）-2,2'：7'，2″：7″，2″′-四分（9,9-二己基芴）（F4）进行合成和表征。随着芴单元数目的增加，它们的热键断裂的起始分解温度和玻璃化转变温度通常增加。在稀甲苯溶液中，寡聚芴在343-370纳米，光致发光最大值从403至410nm的范围内显示出主要吸收峰，和绝对量子产率（Φ PL的高于87％S）。相反，这些化合物在薄膜中的吸收光谱与溶液中的吸收光谱没有很大差异，除了轻微的峰红移（2-8 nm）。
• Combined experimental and theoretical study of one- and two-photon absorption properties of D–π–A–π–D type bis(carbazolylfluorenylethynyl) arene derivatives: Influence of aromatic acceptor bridge
  作者：C. Lavanya Devi、K. Yesudas、Nikolay S. Makarov、V. Jayathirtha Rao、K. Bhanuprakash、Joseph W. Perry

  DOI：10.1016/j.dyepig.2014.09.027

  日期：2015.2

  This article reports the design and synthesis of five new donor-pi-acceptor-pi-donor derivatives where carbazolylfluorenyl serves as donor; arenes serve as central core acceptors, and acetylene group as a it bridge. Comprehensive one- and two-photon absorption properties of these compounds were studied experimentally and theoretically. The two-photon absorption cross-sections were measured by using two-photon excited fluorescence spectrometer and showed significant enhancement from 560 to 2600 GM. In general, the two-photon absorption cross-section values increase with respect to the strength of the acceptor bridge (arenes) in the order of benzene < thiophene < fluorene < anthracene < benzothiadiazole and with the increase of excited state transition dipole moments. The calculated two-photon absorption cross-section values and trends are in good agreement with the experimental results. The combination of large two-photon absorption cross-sections and high emission quantum yields makes the dyes attractive for applications involving two-photon excited fluorescence. (C) 2014 Elsevier Ltd. All rights reserved.
• POLYMER AND ORGANIC LIGHT EMITTING DEVICE INCLUDING POLYMER
  申请人：YANG Hye-yeon

  公开号：US20110175068A1

  公开（公告）日：2011-07-21

  A polymer and an organic light-emitting device including the polymer are provided, wherein the polymer comprises a polymeric unit represented by the Formula: In which variables are as defined herein.