3,6-dibromo-N-decylcarbazole | 188032-43-1

• 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: 3,6-dibromo-N-decylcarbazole
• 英文别名: 3,6-Dibromo-9-decyl-9h-carbazole；3,6-dibromo-9-decylcarbazole
• CAS: 188032-43-1
• 化学式: C₂₂H₂₇Br₂N
• 分子量: 465.271
• InChiKey: BNIRQINVXNCQLS-UHFFFAOYSA-N

物化性质

• 熔点：
  54-56 °C
• 沸点：
  528.8±43.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  3,6-dibromo-N-decylcarbazole 在 2,2'-联吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 1,5-环辛二烯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 96.0h， 以72%的产率得到cyclotetra(N-decylcarbazol-3,6-diyl)
  参考文献：
  名称：

  Ni(COD)2 coupling of 3,6-dibromocarbazoles as a route to all-carbazole shape persistent macrocycles

  摘要：

  The number of applications for carbon-based materials has experienced tremendous growth over the last decade arising from their low toxicity, straight-forward chemical modification, and interesting electronic properties. Among these materials, self-assembled structures based on shape persistent macrocycles are perhaps the most exciting as they offer a means to prepare a wide range of morphologies through reversible assembly of these molecular precursors. In this letter, we report on the preparation of a novel family of all-carbazole shape persistent macrocycles through the simple single-step reaction of the corresponding 3,6-dibromocarbazoles over Ni(COD)(2). The resultant macrocycles display optical properties characteristic of the parent N-alkyl polycarbazoles, with quantum yields ranging from 11% up to 21% suggesting that certain substituents induce the formation of highly emissive aggregates, which could potentially provide a mechanism for the preparation of functional self-assembled nanomaterials. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.08.048
• 作为产物：
  描述：

  9-n-decyl-9H-carbazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 以81%的产率得到3,6-dibromo-N-decylcarbazole
  参考文献：
  名称：

  Development in synthesis and electrochemical properties of thienyl derivatives of carbazole

  摘要：

  A convenient and higher yielding synthetic route to N-alkyl-bis(thiophene)- and N-alkyl-bis(ethylenedioxythiophene) carbazole derivatives is reported and their aggregation, and electrochemical properties are characterized. The key step in the synthesis of this group of compounds has been the Stille-type coupling reaction between the N-alkyldibromocarbazole and tin derivatives of thiophene or ethylenedioxythiophene, as the best way for preparation of conjugated N-alkylcarbazole derivatives. For this group of compounds we also present an electrochemical polymerization effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.142

文献信息

• IRIDIUM COMPLEX, CARBAZOLE DERIVATIVES AND COPOLYMER HAVING THE SAME
  申请人：Lee Jae-Suk

  公开号：US20080177084A1

  公开（公告）日：2008-07-24

  Disclosed are a monomer of iridium complex having a fluoro group as a functional group, a monomer of carbazole derivative having a hydroxy group as the functional group, and a copolymer containing the monomers in its main chain. The iridium complex used as a phosphorescent material and the carbazole derivative having an excellent hole transporting capability are synthesized as the monomer to form the copolymer. The content of iridium complex is easily controlled, and the carbazole derivative and iridium complex are contained in the main chain during the copolymer formation, thereby capable of manufacturing a light emitting device with higher heat resistance and chemical stability.

  揭示了一种含有氟基团的铱配合物单体，一种含有羟基作为功能基团的咔唑衍生物单体，以及在其主链中含有这些单体的共聚物。将作为磷光材料的铱配合物和具有优异传输孔能力的咔唑衍生物合成为单体，形成共聚物。铱配合物的含量易于控制，咔唑衍生物和铱配合物在共聚物形成过程中包含在主链中，因此能够制造具有更高耐热性和化学稳定性的发光器件。
• Polymer Library Comprising Fluorene and Carbazole Homo- and Copolymers for Selective Single-Walled Carbon Nanotubes Extraction
  作者：Fabien Lemasson、Nicolas Berton、Jana Tittmann、Frank Hennrich、Manfred M. Kappes、Marcel Mayor

  DOI：10.1021/ma201890g

  日期：2012.1.24

  To date, (n, m) single-walled carbon nanotubes (SWNTs) cannot be selectively synthesized. Therefore, postprocessing of SWNTs including solubilization and sorting is necessary for further applications. Toward this goal, we have synthesized a polymer library consisting of fluorene- and carbazole-based homo- and copolymers. Variations of the connection of these aromatics together with the incorporation

  迄今为止，不能选择性地合成（n，m）个单壁碳纳米管（SWNT）。因此，SWNT的后处理（包括溶解和分选）对于进一步的应用是必需的。为了实现这一目标，我们合成了一个由芴基和咔唑基均聚物和共聚物组成的聚合物库。这些芳族化合物的连接方式的变化以及其他共轭单体的结合使人们能够获得种类繁多的聚合物。其以选择性涡卷特定（能力Ñ，米）物种朝向的HiPco的SWNT含有多于40（原料调查Ñ，米） 物种。吸收光谱和荧光光谱用于分析SWNT /聚合物悬浮液。这些结果为选择性单壁碳纳米管/聚合物相互作用提供了证据，并允许更详细地评估聚合物的结构与性质之间的关系，从而为单（n，m）单壁碳纳米管萃取聚合物的定制合成铺平了道路。
• 4H-1,2,6-Thiadiazin-4-one-containing small molecule donors and additive effects on their performance in solution-processed organic solar cells
  作者：Felix Hermerschmidt、Andreas S. Kalogirou、Jie Min、Georgia A. Zissimou、Sachetan M. Tuladhar、Tayebeh Ameri、Hendrik Faber、Grigorios Itskos、Stelios A. Choulis、Thomas D. Anthopoulos、Donal D. C. Bradley、Jenny Nelson、Christoph J. Brabec、Panayiotis A. Koutentis

  DOI：10.1039/c4tc02931c

  日期：——

  Donor–acceptor–donors containing 4H-1,2,6-thiadiazinone are presented and used in organic solar cells.

  含有4-1,2,6-噻二唑酮的给体-受体-给体被提出并用于有机太阳能电池。
• Electrochemical and spectroelectrochemical comparison of alternated monomers and their copolymers based on carbazole and thiophene derivatives
  作者：P. Data、P. Zassowski、M. Lapkowski、W. Domagala、S. Krompiec、T. Flak、M. Penkala、A. Swist、J. Soloducho、W. Danikiewicz

  DOI：10.1016/j.electacta.2013.11.167

  日期：2014.3

  conjugation that underwent facile electrochemical polymerization to form stable electroactive polymer. We extended the conjugation of the monomers in comparison to the carbazole and large decrease were observed in the oxidation potential at which polymerization occurs. To lower the oxidation potential of the monomer and control the optical and electronic properties of the polycarbazole, we attached

  在这里，我们报告制备3,6-双（苯甲酰基）-N-癸基咔唑，由于扩展的共轭反应，容易进行电化学聚合反应形成稳定的电活性聚合物，因此具有较低的氧化电位。与咔唑相比，我们扩展了单体的共轭作用，并且观察到发生聚合反应时的氧化电位大大降低。为了降低单体的氧化电位并控制聚咔唑的光学和电子性质，我们在N-取代咔唑的3和6位上连接了噻吩，联噻吩和3,4-乙撑二氧噻吩（EDOT）。通过电子顺磁共振（EPR）和UV-Vis-NIR光谱电化学对单体及其聚合物进行了比较，得出了令人感兴趣的特性。
• Organic Electroluminescence Device, Image Display Apparatus and Lighting Apparatus Including the Same, Charge Transport Material and Charge Transport Layer Forming Ink Including the Same
  申请人：Hatanaka Yumiko

  公开号：US20080054794A1

  公开（公告）日：2008-03-06

  An organic EL device includes a substrate, a first electrode, a luminous layer, a second electrode and a charge transport layer. The charge transport layer is provided between the luminous layer and the first electrode or between the luminous layer and the second electrode. The charge transport layer is made of a charge transport material including a polymeric compound having, in a polymer main chain, a condensed ring structure composed of a plurality of rings including a pyrrole ring with the main chain being a conjugated system.

  一种有机电致发光器件包括基板、第一电极、发光层、第二电极和电荷传输层。电荷传输层位于发光层和第一电极或发光层和第二电极之间。电荷传输层由电荷传输材料制成，其中包括一种聚合物化合物，其在聚合物主链中具有由多个环组成的缩合环结构，包括一个吡咯环，主链是一个共轭系统。