3,11-dicyano-2,10-diethoxy-4,12-diphenyl-6,7-dihydrobenzo<1,2-b:3,4-b'>-1,8-dinaphthyridine | 174838-93-8

• 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: 3,11-dicyano-2,10-diethoxy-4,12-diphenyl-6,7-dihydrobenzo<1,2-b:3,4-b'>-1,8-dinaphthyridine
• 英文别名: 3,11-dicyano-2,10-diethoxy-4,12-diphenyl-6,7-dihydro-benzo[1,2-b:3,4-b']bi[1,8]naphthyridine；3,11-dicyano-2,10-diethoxy-4,12-diphenyl-6,7-dihydrobenzo[1,2-b:3,4-b']1,8-binaphthyridine；6,18-Diethoxy-8,20-diphenyl-3,5,15,17-tetrazapentacyclo[12.8.0.02,11.04,9.016,21]docosa-1(14),2,4,6,8,10,15,17,19,21-decaene-7,19-dicarbonitrile
• CAS: 174838-93-8
• 化学式: C₃₆H₂₆N₆O₂
• 分子量: 574.641
• InChiKey: XEEGNPFXCZGNPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,11-dicyano-2,10-diethoxy-4,12-diphenyl-6,7-dihydrobenzo<1,2-b:3,4-b'>-1,8-dinaphthyridine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以60%的产率得到3,11-dicyano-2,10-diethoxy-4,12-diphenylbenzo[1,2-b:3,4-b']bi[1,8]naphthyridine
  参考文献：
  名称：

  Synthesis of new bis(2-[1,8]naphthyridinyl) bridging ligands with multidentate binding sites

  摘要：

  A series of new 2-[1,8]naphthyridinyl and bis(2-[1,8]naphthyridinyl) bridging ligands with multidentate binding sites were prepared using 2-amino-5-cyano-6-ethoxy-4-phenyl-3-carbaldehyde pyridine as excellent Friedlander synthon. Condensation with a series of acetyl(heteroaryl)-aromatics provides the corresponding 2-aryl(heteroaryl)-1,8-naphthyridines. Reaction with 1,3-diacetylbenzene, 2,6-diacetylpyridine or 4-tertbutyl-2.6-diacetylpyridine provides the expected Friedlander product. Similar 2:1 condensation with 1,4-diacetylbenzene, 4,4'-diacetylbiphenyl, 1,4- and 1,6-diacetylpyrene, 2,6-diacetylpyrazine or 2,3-butanedione leads to a family of six new bis-1,8-nap ligands. The reaction with cyclic 1.2- or 1.3-diketones affords 3,3'-annelated derivatives of all-syn or all-trans planar 2,2'-nap, respectively. Examination of the electronic absorption and emission spectra of the bridging ligands was realized. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.017
• 作为产物：
  描述：

  2-amino-5-cyano-6-ethoxy-3-formyl-4-phenylpyridine 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 3,11-dicyano-2,10-diethoxy-4,12-diphenyl-6,7-dihydrobenzo<1,2-b:3,4-b'>-1,8-dinaphthyridine
  参考文献：
  名称：

  A Friedländer Approach to Polycondensed 1,8-Naphthyridine Derivatives

  摘要：

  DOI：

  10.3987/com-95-7206

文献信息

• Novel naphthyridine-based compounds in small molecular non-doped OLEDs: synthesis, properties and their versatile applications for organic light-emitting diodes
  作者：Antonio Fernández-Mato、José M. Quintela、Carlos Peinador

  DOI：10.1039/c2nj40279c

  日期：——

  A series of six new n-type conjugated 1,8-naphthyridine oligomers were examined in organic light emitting diodes (OLEDs). The compounds show a high fluorescence in both solution (10−8 M) and the solid state. The naphthyridines have high glass-transition (Tg = 65–105 °C) and decomposition (Td = 380–400 °C) temperatures, reversible electrochemical reduction, and high electron affinities (2.79–3.00 eV). Systematic variation of the spacer linkage can modulate and fine-tune their properties. They emit high blue, green and yellow photoluminescence with 0.70–1.0 quantum yields. Good-performance, single-layer emitter OLEDs with yellow to white-pink emission have also been demonstrated using these materials. White-pink emitter give a performance with a high brightness (400 cd m−2 at 4 V), and 0.6 cd A−1. Yellow emitters give the best performance with maximum brightness of 250 cd m−2 with a maximum current efficiency of 1.2 cd A−1. These results demonstrate the potential of this new class of n-type conjugated oligomers as emitters and electron-transport materials for developing high-performance yellow to white-pink OLEDs.

  在有机发光二极管（OLED）中研究了一系列六种新型 n 型共轭 1,8-萘啶低聚物。这些化合物在溶液（10-8 M）和固态下都显示出较高的荧光。萘啶类化合物具有较高的玻璃转化温度（Tg = 65-105 ℃）和分解温度（Td = 380-400 ℃）、可逆的电化学还原性和较高的电子亲和力（2.79-3.00 eV）。间隔连接的系统变化可以调节和微调它们的特性。它们能发出蓝色、绿色和黄色的高光致发光，量子产率为 0.70-1.0。利用这些材料还展示了性能良好的单层发射器有机发光二极管，可发出黄色至白粉色的光。白粉色发光体具有高亮度（4 V 时为 400 cd m-2）和 0.6 cd A-1 的性能。黄色发光体的性能最好，最大亮度为 250 cd m-2，最大电流效率为 1.2 cd A-1。这些结果证明了这一新型 n 型共轭低聚物作为发光体和电子传输材料在开发高性能黄色至白色粉红色有机发光二极管方面的潜力。