7-bromo-9,9'-dihexyl-9H-fluorene-2-carbonitrile | 403699-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 7-bromo-9,9'-dihexyl-9H-fluorene-2-carbonitrile
• 英文别名: 7-Bromo-9,9-dihexylfluorene-2-carbonitrile
• CAS: 403699-44-5
• 化学式: C₂₆H₃₂BrN
• 分子量: 438.451
• InChiKey: DYOUREWVOMSQOU-UHFFFAOYSA-N

物化性质

• 沸点：
  527.7±43.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-bromo-9,9'-dihexyl-9H-fluorene-2-carbonitrile 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以68%的产率得到2,4,6-tris(7-bromo-9,9-dihexyl-9H-fluoren-2-yl)-1,3,5-triazine
  参考文献：
  名称：

  具有1,3,5-三嗪核和N-芳基发色团取代的芴臂的星形D-π-A化合物：合成，聚集诱导的发射和双光子吸收

  摘要：

  设计并合成了三种具有1,3,5-三嗪核心和N-芳基生色团（3,6-二叔丁基咔唑，吩恶嗪和吩噻嗪）取代的芴臂的星形D-π-A化合物。通过光谱学和理论方法对它们的光物理性质进行了系统的研究。所有化合物显示出强的1点在UV区和强烈的π-π*跃迁1个π-π* /分子内电荷转移（1个ICT）吸收带在UV-VIS区域。1个ICT波段的红移由给电子N引起-芳基发色团。所有化合物在溶剂中均表现出聚集诱导的发射性质，在固态中具有相对较高的量子效率（Φ  = 10％–20％）。而且，这些化合物由于其良好的平面性和大的π共轭而显示出双光子吸收（TPA）性质。TPA的最大横截面值在800 nm时可达5000 GM。多功能的特性使这些化合物成为有机发光材料和双光子生物成像应用的潜在候选者。

  DOI：

  10.1016/j.dyepig.2016.10.015
• 作为产物：
  描述：

  2-cyano-9,9-dihexylfluorene 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以58%的产率得到7-bromo-9,9'-dihexyl-9H-fluorene-2-carbonitrile
  参考文献：
  名称：

  腈振动探测阴离子的电子定位

  摘要：

  电子的定域和离域是化学中的一个关键概念，是决定电子通过有机共轭分子传输效率的重要因素之一，有机共轭分子具有充当“分子线”的潜力。这反过来又会显着影响有机太阳能电池和其他分子电子器件的效率。还需要了解一维共轭链中的电子能量格局和控制电子传输能力的动力学，以便我们可以更好地定义共轭分子的设计原则以用于其应用。我们通过利用时间分辨红外检测与脉冲辐射分解相结合，表明腈 ν(C≡N) 振动对腈取代的有机阴离子中电子定位的程度做出响应。一系列芳基腈阴离子的测量使我们能够在 ν(C≡N) 红外 (IR) 位移的变化与腈类中电荷从中性状态到阴离子状态的变化之间构建半经验校准曲线；腈阴离子中更多的电子定位导致更大的红外位移。此外，阴离子中的 IR 线宽可以报告伴随电子密度分布变化的结构变化。探测腈 ν(C≡N) IR 振动带的位移使我们能够确定电子如何定位在腈官能化的低聚芴的阴离子中，被认为是有机混合价化合

  DOI：

  10.1021/jacs.5b04648

文献信息

• Synthesis and Two-Photon Properties of Small Dendritic Chromophores with Symmetrical and Unsymmetrical Substituted Skeletons
  作者：Tzu-Chau Lin、Ying-Hsuan Lee、Chia-Ling Hu、Yu-Kai Li、Yu-Jhen Huang

  DOI：10.1002/ejoc.201101485

  日期：2012.3

  A set of novel multi-branched chromophores consisting of two groups of fluorene/oxadiazole-based analogues with generic skeletons of donor-π-acceptor (unsymmetrical) and donor-π-acceptor-π-donor (symmetrical) type has been synthesized and shown to display strong and broadly dispersed two-photon absorptivities in the near infrared (NIR) region on irradiation with femtosecond laser pulses. It is also

  一组新型多支化发色团由两组芴/恶二唑类类似物组成，具有供体-π-受体（不对称）和供体-π-受体-π-供体（对称）类型的通用骨架已被合成并显示在飞秒激光脉冲照射下，在近红外 (NIR) 区域显示强且广泛分散的双光子吸收率。还证明了结构参数，例如连接的供体单元的数量和取代模式，与这些模型化合物的分子双光子活性密切相关。
• Two-photon absorption and effective optical power-limiting properties of small dendritic chromophores derived from functionalized fluorene/oxadiazole units
  作者：Tzu-Chau Lin、Ying-Hsuan Lee、Bor-Rong Huang、Chia-Ling Hu、Yu-Kai Li

  DOI：10.1016/j.tet.2012.04.073

  日期：2012.6

  A set of novel multi-branched chromophores composed of four analogues with generic skeletons of donor-π-acceptor (D-π-A) derived from functionalized fluorene/oxadiazole moieties has been synthesized and experimentally shown to possess strong and wide-dispersed two-photon absorptivities in near infrared (NIR) region under the irradiation of femtosecond laser pulses. It is demonstrated that structural

  合成了一组新颖的多支发色团，该发色团由四个类似物组成，这些类似物具有衍生自功能化芴/恶二唑基团的供体-π-受体（D-π-A）的一般骨架，并通过实验证明其具有强而分散的两个飞秒激光脉冲辐照下近红外（NIR）区域的光子吸收率。结果表明，结构参数，例如π骨架的大小和所连接的给电子单元的数量与这些模型化合物的分子双光子活性密切相关。
• NOVEL HETEROCYCLIC FLUORESCENT DYES AND METHOD OF PRODUCTION THEREOF
  申请人：BASF SE

  公开号：US20150380660A1

  公开（公告）日：2015-12-31

  The invention relates to novel compounds of formula (III) that can be used as heterocyclic dyes of unique structure and properties. These compounds can be obtained in a three-step synthesis from simple substrates. The compounds according to the invention have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the compounds according to the invention are used in organic field effect transistors, organic photovoltaics (solar cells) and photodiodes.

  本发明涉及一种新型化合物(III)的配方，可用作具有独特结构和性质的杂环染料。这些化合物可以从简单的底物中通过三步合成得到。本发明中的化合物在有机溶剂中具有优异的溶解性和优异的膜形成性能。此外，当本发明中的化合物用于有机场效应晶体管、有机光伏(太阳能电池)和光电二极管时，可以观察到高能量转换效率、优异的场效应迁移率、良好的开/关电流比和/或优异的稳定性。
• Sterically Hindered Fluorenyl-Substituted Poly(<i>p</i>-phenylenevinylenes) for Light-Emitting Diodes
  作者：Sang Ho Lee、Bo-Bin Jang、Tetsuo Tsutsui

  DOI：10.1021/ma010643e

  日期：2002.2.1

  A new series of processable dihexylfluorenyl-substituted poly(p-phenylenevinylene) derivatives (DHF-PPVs) were synthesized by dehydrohalogenation-condensation polymerization (GILCH polymerization). The polymers were characterized by NMR, FT-IR, and elemental analysis and were completely soluble in common organic solvents, All of the polymers demonstrated bright blue-green emission with high photoluminescence (PL) efficiencies of 68-71% in chloroform, good thermal stability with decomposition temperatures above 322degreesC, and high glass transition temperatures in the range of 113-148degreesC. Cyclic voltammetry studies revealed that these polymers undergo both irreversible oxidation and reduction onsets around 0.9 and -1.5 V, which are attributed to the conjugated backbone. Polymer light-emitting diodes (PLEDs), fabricated with DHF-PPVs, as the emitting layer, poly(3,4-ethylenedioxythiophene) (PEDOT) doped with poly(styrenesulfonic acid) (PSS) (PEDOT:PSS), as the hole injection/ transporting layer, Ca cathodes, and indium-tin oxide (ITO) anodes, (ITO/PEDOT:PSS/DHF-PPVs/Ca), emitted blue-green emission with a maximum peak around 500 nm and a shoulder peak around 532 nm. For the poly[2-(9,9-dihexylfluorenyl)-1,4-phenylenevinylene] (DHF-PPV) device, a low turn-on voltage of 2.8 V (0.13 MV/cm), a maximum luminance of 12 000 cd/m(2) at 0.4 MV/cm, and a maximum external quantum efficiency of 0.53% were obtained, The latter was 33-37 times brighter and 1.6-2.8 times more efficient than those devices with poly[2-(7-methoxy-9,9-dihexylfluorenyl)-1,4-phenylenevinylene] (MDHF-PPV) and poly[2-(7-cyano-9,9-dihexylfluorenyl)-1,4-phenylenevinylene] (CNDHF-PPV).
• Synthesis, Light-Emitting, and Two-Photon Absorption Properties of Platinum-Containing Poly(arylene-ethynylene)s Linked by 1,3,4-Oxadiazole Units
  作者：Thomas Goudreault、Ze He、Yanhe Guo、Cheuk-Lam Ho、Hongmei Zhan、Qiwei Wang、Keith Yat-Fung Ho、Ka-Leung Wong、Daniel Fortin、Bing Yao、Zhiyuan Xie、Lixiang Wang、Wai-Ming Kwok、Pierre D. Harvey、Wai-Yeung Wong

  DOI：10.1021/ma1009319

  日期：2010.10.12

  A series of soluble and thermally stable group 10 platinum(II) polyyne polymers of the type [-C equivalent to C- P1(PBu3)(2)-C equivalent to C-Ar-Ox-Ar-](n) (where Ox = 1,3,4-oxadiazole, Ar = p-C6H4 or 2,7-dihexy]-9.9-fluorene) and [-C equivalent to C-Pt(PBu3)(2)-C equivalent to C-Ar-Ox-Ar-Ox-Ar](n) (where Ar = 2,7-dihexy]-9.9-fluorene) along with their corresponding dinuclear model compounds [Ph-P1(PEt3)(2)-C equivalent to C-Ar-l(2)-Ox-(where Ar = p-C6H4 or 2,7-dihexy1-9,9-fluorene) and [Ph-Pt(PEt3)(2)-C equivalent to C-Ar-Ox-](2)-Ar- (where Ar = 2,7-dihexyl-9,9-fluorene) were prepared and characterized. The regiochemical structure of the polymers has been ascertained by single-crystal X-ray analysis on the model compound [Ph-Pt(PEt3)(2)-C equivalent to C-p-C6H4-l(2)-Ox- The photophysical properties (absorption, excitation, emission, and nanosecond transient absorption spectra) of these metalated compounds in 2MeTHF at 298 and 77 K are reported. These findings are correlated by density functional theory (DFT) calculations. Geometry optimizations predict totally planar molecules for these metalated complexes and polymers, allowing better pi-conjugation across the main chain. The ligands are strongly fluorescent but become also phosphorescent when the Pt atom is introduced in the backbone of the conjugated organometa Hie complexes and polymers. These emissions arc assigned to pi pi* transitions in all cases involving the Ptd(xy) orbitals. These Pt compounds exhibit two-photon absorption (2PA), and their 2PA cross sections (sigma 2) have been determined. The potential of exploiting such metallopolymers for the design of electrophosphorescent polymer light-emitting devices (PLEDs) and their use as single-dopant for white PLEDs have also been discussed.