6,12-二氢茚并[1,2-B]芴 | 486-52-2

• 物质功能分类: 医药中间体 - OLED材料中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 6,12-二氢茚并[1,2-B]芴
• 英文名称: 6,12-dihydroindeno[1,2-b]fluorene
• 英文别名: indenofluorene
• CAS: 486-52-2
• 化学式: C₂₀H₁₄
• 分子量: 254.331
• InChiKey: QBBPWJMJLXOORS-UHFFFAOYSA-N

物化性质

• 熔点：
  216 °C
• 沸点：
  452.5±25.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存放于室温、干燥且密封的环境中。

反应信息

• 作为反应物：
  描述：

  6,12-二氢茚并[1,2-B]芴 在 aluminum oxide 、 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 copper(ll) bromide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 、 甲苯 为溶剂， 反应 25.5h， 生成 8-bromo-6,6,12,12-tetrakis(2-ethylhexyl)-N,N-diphenyl-6,12-dihydroindeno[1,2-b]fluoren-2-amine
  参考文献：
  名称：

  Coplanar indenofluorene-based organic dyes for dye-sensitized solar cells

  摘要：

  A series of new organic dyes, comprising indenofluorene moiety as a conjugated bridge, with an extended pi-groups, such as thiophene and furan, diphenylamine as donor, cyanoacrylic acid group as an electron acceptor and anchoring group, have been synthesized. Photophysical and electrochemical measurements, and theoretical computation were carried out on these dyes. Dye-sensitized solar cells (DSSCs) using these dyes as the sensitizers exhibited photocurrent density (J(sc)), open-circuit voltage (V-OC), and fill factor (FF) in the range of 6.95-8.20 mA/cm(2), 0.70-0.71 V, and 0.69-0.71, respectively, corresponding to an overall conversion efficiency of 3.36-4.05%. The best efficiency reached 56% of the standard cell based on N719. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.045
• 作为产物：
  描述：

  4b,5,5a,6,10b,11,11a,12-octahydro-indeno[1,2-b]fluorene 在 palladium on activated charcoal 作用下， 生成 6,12-二氢茚并[1,2-B]芴
  参考文献：
  名称：

  722.大环炔化合物。第二部分 1,2：7,8-二苯并环十二烷基-1,7-二烯-3,5,9,11-丁炔

  摘要：

  DOI：

  10.1039/jr9600003614

文献信息

• Synthesis of Methylene-Bridge Polyarenes through Palladium-Catalyzed Activation of Benzylic Carbon-Hydrogen Bond
  作者：Chien-Chi Hsiao、Yi-Kuan Lin、Chia-Ju Liu、Tsun-Cheng Wu、Yao-Ting Wu

  DOI：10.1002/adsc.201000651

  日期：2010.12.17

  In the presence of palladium(II) acetate [Pd(OAc)2] and an N-heterocyclic carbene (NHC) ligand, fluorene derivatives can be generated in good to excellent yields from 2-halo-2′-methylbiaryls through the benzylic CH bond activation (14 examples; 81–97% yields). The scope and limitations of this protocol have been examined. A wide range of functional groups, such as alkyl, alkoxy, ester, nitrile, and

  在乙酸钯（II）[Pd（OAc）2 ]和N-杂环卡宾（NHC）配体的存在下，芴衍生物可以从2-卤代2'-甲基联芳基通过苄基CH生成高至极好的收率键活化（14个例子；产率81-97％）。已经检查了该协议的范围和局限性。各种各样的官能团，例如烷基，烷氧基，酯，腈和其他，能够耐受本文的反应条件。同位素标记的联苯的环化反应产生相应的产物，具有主要的动力学同位素效应（k H / k D＝ 4.8∶1），这表明该反应的决定速率的步骤是苄基CH键的活化。此外，从三联苯中也获得了茚并芴的优异结果（3个实例；产率为91-92％）。2，6-二氯-2'-甲基联苯与二苯乙炔的级联反应通过芳基和苄基CH键的活化，以60％的收率产生了8,9-二苯基-4 H-环戊[ def ]菲。
• Nitrogenous heterocyclic derivative and organic electroluminescence device making use of the same
  申请人：Idemitsu Kosan Co., Ltd.

  公开号：US08058450B2

  公开（公告）日：2011-11-15

  A novel nitrogen-containing heterocyclic compound having a specific structure and an organic electroluminescence device comprising an anode, a cathode and an organic thin film layer which comprises a single layer or a plurality of layers comprising at least a light emitting layer and is disposed between the anode and the cathode, wherein at least one layer in the organic thin film layer comprises the above nitrogen-containing heterocyclic derivative singly or as a component of a mixture. The organic electroluminescence device exhibits a great luminance of emitted light and a great efficiency of light emission even under application of a low voltage.

  一种具有特定结构的含氮杂环化合物，以及包括阳极、阴极和有机薄膜层的有机电致发光器件，所述有机薄膜层包括单层或多层，至少包括一个发光层，并位于阳极和阴极之间，其中有机薄膜层中的至少一层包括上述含氮杂环衍生物单独或作为混合物成分。该有机电致发光器件在施加低电压时表现出较高的发光亮度和较高的发光效率。
• Planarity of terphenyl rings possessing <i>o</i>-carborane cages: turning on intramolecular-charge-transfer-based emission
  作者：Hyunhee So、Jea Ho Kim、Ji Hye Lee、Hyonseok Hwang、Duk Keun An、Kang Mun Lee

  DOI：10.1039/c9cc07729d

  日期：——

  To clarify the relationship between planarity and intramolecular charge transfer (ICT), two o-carboranyl compounds (TCB and FCB) containing different ortho-type terphenyl rings, namely, perfectly distorted or planar phenyl rings, were synthesised and fully characterised. Although the emission spectra of both compounds presented intriguing dual-emission patterns in solution at 298 or 77 K and in the

  为了阐明平面度和分子内电荷转移（ICT）之间的关系，合成了两个具有完全异形或平面苯环的邻位三联苯环的邻邻碳烷基化合物（TCB和FCB）。尽管两种化合物的发射光谱在298或77 K的溶液中均处于薄膜状态并呈现出有趣的双发射模式，但扭曲的TCB大多显示出局部激发发射，而平面FCB则显示出与ICT跃迁相对应的强发射。有趣的是，基于三联苯的邻苯二甲醛的发射效率和辐射衰减常数通过增加三联苯基的平面度，逐渐增强了-碳硼烷基化合物。这些结果证明了在邻-甲硼烷取代的化合物中，附加的芳基的平面度与基于ICT的辐射衰减之间存在很强的关系。
• ELECTROLUMINESCENT COMPOUNDS WITH HIGH EFFICIENCY AND ORGANIC LIGHT-EMITTING DIODE USING THE SAME
  申请人：Shin Hyo Nim

  公开号：US20110152587A1

  公开（公告）日：2011-06-23

  The present invention relates to novel organic electroluminescent compounds and an organic light-emitting diode comprising the same. The organic electroluminescent compounds according to the present invention exhibit high luminous efficiency and excellent life property as a material, so that an OLED device having very good operation life can be prepared therefrom.

  本发明涉及新型有机电致发光化合物以及包括这些化合物的有机发光二极管。根据本发明的有机电致发光化合物表现出高发光效率和优异的寿命特性作为材料，因此可以制备具有非常良好运行寿命的OLED器件。
• A General Synthetic Route to Indenofluorene Derivatives as New Organic Semiconductors
  作者：Tayebeh Hadizad、Jidong Zhang、Zhi Yuan Wang、Timothy C. Gorjanc、Christophe Py

  DOI：10.1021/ol0476570

  日期：2005.3.1

  A series of 2,6-disubstituted indenofluorene derivatives were obtained in high purity via a general route involving the Suzuki coupling reaction. The potential of these conjugated indenofluorenes as new organic semiconductors was demonstrated by the light-emitting diode reaching a high luminance of 1400 Cd/m(2) below 10 V. [structure: see text]

  通过涉及Suzuki偶联反应的一般途径，以高纯度获得了一系列2，6-二取代的茚并芴衍生物。通过在10 V以下达到1400 Cd / m（2）的高亮度的发光二极管，证明了这些共轭茚芴作为新型有机半导体的潜力。