2,2'-(1,4-phenylenedivinylene)bisquinoxaline | 115388-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,2'-(1,4-phenylenedivinylene)bisquinoxaline
• 英文别名: 1,4-bis-(2-quinoxalin-2-yl-vinyl)-benzene；1,4-Bis-(2-chinoxalin-2-yl-vinyl)-benzol；2,2'-(1,4-Phenylenedivinylene)bis-quinoxaline；2-[(E)-2-[4-[(E)-2-quinoxalin-2-ylethenyl]phenyl]ethenyl]quinoxaline
• CAS: 115388-42-6
• 化学式: C₂₆H₁₈N₄
• 分子量: 386.456
• InChiKey: BZRCPXWUYMATAR-WXUKJITCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基喹喔啉 、 对苯二甲醛 在 乙酸酐 作用下， 反应 40.0h， 以75%的产率得到2,2'-(1,4-phenylenedivinylene)bisquinoxaline
  参考文献：
  名称：

  Synthesis of a new conjugated 2,2′-(1,4-phenylenedivinylene)bis-quinoxaline and a series of styryl derivatives of quinoxaline and quinoline as promising electro- and photoluminescent materials

  摘要：

  A new poly(p-phenylenedivinylene) oligomer 2,2'-(1,4-phenylenedivinylene)bisquinoxaline, a promising candidate in organic electroluminescent devices, was synthesised via a Knoevenagel condensation reaction of 2-methylquinoxaline with 1,4-benzenedicarbaldehyde. The same synthetic strategy was applied to obtain substituted styryl dyes, derivatives of quinoxaline, whereas styryl derivatives of quinoline were prepared by "Anil Synthesis". The considered dyes are of interest as fluorescence emitting materials.

  DOI：

  10.1007/s10593-009-0229-3

文献信息

• 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。
• US8507896B2
  申请人：——

  公开号：US8507896B2

  公开（公告）日：2013-08-13
• Synthesis of a new conjugated 2,2′-(1,4-phenylenedivinylene)bis-quinoxaline and a series of styryl derivatives of quinoxaline and quinoline as promising electro- and photoluminescent materials
  作者：B. Bachowska、G. Matusiak

  DOI：10.1007/s10593-009-0229-3

  日期：2009.1

  A new poly(p-phenylenedivinylene) oligomer 2,2'-(1,4-phenylenedivinylene)bisquinoxaline, a promising candidate in organic electroluminescent devices, was synthesised via a Knoevenagel condensation reaction of 2-methylquinoxaline with 1,4-benzenedicarbaldehyde. The same synthetic strategy was applied to obtain substituted styryl dyes, derivatives of quinoxaline, whereas styryl derivatives of quinoline were prepared by "Anil Synthesis". The considered dyes are of interest as fluorescence emitting materials.