1,4-Bis<β-(2-quinolyl)vinyl>benzene | 29820-79-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,4-Bis<β-(2-quinolyl)vinyl>benzene
• 英文别名: 1,4-di-<β-(2-quinolyl)vinyl>benzene；2,2'-(1,4-phenylenedivinylene)bisquinoline；1,4-bis-(trans-2-[2]quinolyl-vinyl)-benzene；1,4-Bis-(trans-2-[2]chinolyl-vinyl)-benzol；1,4-Bis(2-(2-quinolinyl)ethenyl)-benzene；2-[(E)-2-[4-[(E)-2-quinolin-2-ylethenyl]phenyl]ethenyl]quinoline
• CAS: 29820-79-9
• 化学式: C₂₈H₂₀N₂
• 分子量: 384.48
• InChiKey: DJDHBLKJOAHWQU-HBKJEHTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  喹啉-2-甲醛 、 1,4-xylylene-bis(triphenylphosphonium chloride) 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以48%的产率得到1,4-Bis<β-(2-quinolyl)vinyl>benzene
  参考文献：
  名称：

  Polymers and oligomers, their synthesis, and electronic devices incorporating same

  摘要：

  这项发明涉及聚合物和寡聚物，它们的合成方法，以及包含它们的电子设备。

  公开号：

  US20050187375A1

文献信息

• Synthesis, characterization, photoluminescent and electroluminescent properties of new conjugated 2,2′-(arylenedivinylene)bis-8-substituted quinolines
  作者：Fushun Liang、Jiangshan Chen、Yanxiang Cheng、Lixiang Wang、Dongge Ma、Xiabin Jing、Fosong Wang

  DOI：10.1039/b210408c

  日期：——

  A series of new PPV oligomers containing 8-substituted quinoline, 2,2′-(arylenedivinylene)bis-8-quinoline derivatives, were designed and synthesized via a Knoevenagel condensation reaction of quinaldine, 8-hydroxy- or 8-methoxy-quinaldine with aromatic dialdehydes. These PPV oligomers were characterized by 1H and 13C-NMR, X-ray diffraction, elemental analysis, UV-visible and fluorescence spectroscopies. The X-ray diffraction investigation showed that there are intermolecular π⋯π interactions in the solid state in 1 and 3. The optical and photoluminescent properties study demonstrated that the emission color of the resulting materials varies from blue to yellow and is dependent on the substituents (π-donor and π-acceptor groups) on both sides of the conjugated molecules and the aromatic core in the middle of the conjugated backbones. The electroluminescent devices using compounds 1–4 as the emitters and electron-transporting layers were fabricated with the structure ITO/NPB/emitter/LiF/Al. The best device performance with the maximum brightness of 5530 cd m−2 and the luminous efficiency of 2.4 cd A−1 is achieved by using compound 4, with intramolecular charge transfer character, as the emitter; these values represent a more than 5-fold improvement in brightness and efficiency compared to compound 3 without methoxy groups on the phenyl rings.

  通过喹哪啶、8-羟基或 8-甲氧基喹哪啶与芳香族二醛的克诺文纳格尔缩合反应，设计并合成了一系列含有 8-取代喹啉的新型 PPV 低聚物，即 2,2â²-（芳基二乙烯）双-8-喹啉衍生物。这些 PPV 低聚物通过 1H 和 13C-NMR、X 射线衍射、元素分析、紫外-可见光谱和荧光光谱进行表征。X 射线衍射研究表明，1 和 3 在固态下存在分子间的 Ïâ¯Ï 相互作用。光学和光致发光特性研究表明，所得材料的发射颜色从蓝色到黄色不等，取决于共轭分子两侧的取代基（Ï-供体基团和Ï-受体基团）以及共轭骨架中间的芳香族核心。以化合物 1â4 为发光体和电子传输层，制成了结构为 ITO/NPB/emitter/LiF/Al 的电致发光器件。使用具有分子内电荷转移特性的化合物 4 作为发射体，实现了最佳的器件性能，最大亮度为 5530 cd mâ2，发光效率为 2.4 cd Aâ1；与苯环上不含甲氧基的化合物 3 相比，亮度和效率提高了 5 倍以上。
• COMPOUNDS HAVING ELECTROLUMINESCENT OR ELECTRON TRANSPORT PROPERTIES
  申请人：Kathirgamanathan Poopathy

  公开号：US20110006295A1

  公开（公告）日：2011-01-13

  A compound of the formula R 1 (CR 3 ═CR 4 )nAr(CR 4 ═CR 3 ) n R 2 wherein: n is 0 or 1; Ar represents aryl or heteroaryl having 1-5 aromatic rings which may be chain or fused or a combination of chain and fused, which may be substituted with alkoxy, fluoro, fluoroalkyl or cyano and which in the case of a 5-membered ring nitrogen heteroatom may be N-substituted with aryl or substituted aryl optionally further substituted with alkoxy, fluoro, fluoroalkyl or cyano; R 1 and R 2 independently represent aryl or nitrogen, oxygen or sulphur-containing heteroaryl having two to four fused aromatic rings one of which may be 5-membered and optionally substituted by aryl or heteroaryl having 1-5 chain or fused aromatic rings which may be further substituted with alkoxy, fluoro, fluoroalkyl or cyano; and R 3 and R 4 independently represent hydrogen, methyl, ethyl or benzyl. Also provided is a method of making a compound having electroluminescent and/or electroconductive properties, which comprises condensing an aromatic dialdehyde with a methyl-substituted heteroaryl compound having two to four fused rings which maybe unsubstituted or may be further substituted by aryl or heteroaryl having from one to four aromatic rings, said aryl or heteroaryl substituent or substituents optionally being substituted with one or more fluoro, fluoroalkyl or cyano substituents. The condensation may be carried out in acetic anhydride under reflux. The compounds may be incorporated e.g. as an electron transport layer into an optical light emitting diode, where embodiments can provide high electron mobility, low turn-on voltage and good lifetime, or into an electrostatic imaging member. A composition is provided comprising a compound as above and a second host or electron transport material and/or at least one dopant.

  该化合物的化学式为R1(CR3═CR4)nAr(CR4═CR3)nR2，其中：n为0或1；Ar代表芳香族或杂环芳香族，具有1-5个芳香环，可以是链式的、融合的或链式和融合的组合，可以用烷氧基、氟、氟烷基或氰基取代，在5-成员环氮杂原子的情况下，可以用芳基或取代芳基N-取代，可选择进一步用烷氧基、氟、氟烷基或氰基取代；R1和R2独立地代表芳基或含有两个到四个融合芳香环的氮、氧或硫杂环，其中一个可能是5-成员环，并可选择用具有1-5个链式或融合芳香环的芳基或杂环芳基进一步取代，这些芳基或杂环芳基可能进一步用烷氧基、氟、氟烷基或氰基取代；R3和R4独立地代表氢、甲基、乙基或苄基。还提供了一种具有电致发光和/或电导性能的化合物的制备方法，该方法包括将芳香二醛与具有两到四个融合环的甲基取代杂环化合物缩合，该杂环化合物可以是未取代的或进一步由具有1到4个芳香环的芳基或杂环芳基取代，该芳基或杂环芳基取代基可选择进一步用一个或多个氟、氟烷基或氰基取代。缩合可以在乙酸酐中回流进行。这些化合物可以被用作电子传输层，例如被纳入到光学发光二极管中，其中实施例可以提供高电子迁移率、低开启电压和良好的寿命，或被纳入到静电成像成员中。还提供了一种组合物，包括上述化合物和第二宿主或电子传输材料和/或至少一种掺杂剂。
• Electroluminescence device
  申请人：IDEMITSU KOSAN COMPANY LIMITED

  公开号：EP0373582A1

  公开（公告）日：1990-06-20

  Disclosed is an electroluminescence device (EL device) in which an emitting material is made of an organic compound represented by general formula (I) or (II): X-CH=CH-Y-CH=CH-Z      (I) X-CH=CH-Z      (II) wherein all the symbols are as defined in the specification. The EL device displays a high brightness by applying only low voltage.

  本发明公开了一种电致发光装置（EL 装置），其中的发光材料由通式 (I) 或 (II) 所代表的有机化合物制成： X-CH=CH-Y-CH=CH-Z (I) X-CH=CH-Z (II) 其中所有符号在说明书中均有定义。 EL 装置只需施加低电压即可显示高亮度。
• Steinkopf; Hanske, Justus Liebigs Annalen der Chemie, 1939, vol. 541, p. 238,257
  作者：Steinkopf、Hanske

  DOI：——

  日期：——
• Ried; Hinsching, Justus Liebigs Annalen der Chemie, 1956, vol. 600, p. 47,58
  作者：Ried、Hinsching

  DOI：——

  日期：——