3,8-dicyanobenzo[c]cinnoline | 1388860-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 3,8-dicyanobenzo[c]cinnoline
• CAS: 1388860-54-5
• 化学式: C₁₄H₆N₄
• 分子量: 230.228
• InChiKey: UFMWBJCSVHCNCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.36
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,8-dicyanobenzo[c]cinnoline 在 水 、 potassium hydroxide 作用下， 以 二乙二醇 为溶剂， 反应 12.0h， 以52%的产率得到benzo[c]cinnoline-3,8-dicarboxylic acid
  参考文献：
  名称：

  Investigations on the electrochemical properties of new conjugated polymers containing benzo[c]cinnoline and oxadiazole moieties

  摘要：

  A four-step route was designed to synthesize 3,8-benzo[c]cinnoline dicarboxylic acid (4). New conjugated polymers, POXD (I) and POXD (T), containing benzo[c]cinnoline and oxadiazole moieties, were obtained by thermal cyclodehydration of their soluble polyhydrazide precursors PHA (I) and PHA (T), respectively. Two reduction peaks were observed for these new conjugated polymers during CV cathodic scan. From the CV voltammograms combined with the results from molecular simulation, we concluded that the first reduction occurred at oxadiazole moiety and benzo[c]cinnoline moiety was responsible for the second reduction. It indicates that oxadiazole has stronger electron affinity than benzo[c]cinnoline. We proposed a mechanism to explain this two-stage reduction process. Due to the planar and electron-accepting ability of benzo[c]cinnoline and oxadiazole moieties, POXD (I) and POXD (T) exhibited very low LUMO (-3.42 and -3.45 eV) and HOMO (-6.23 and -6.27 eV) energy levels. They can be used as hole-blocking or electron-injection layers for OLED applications. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.10.059
• 作为产物：
  描述：

  4,4'-二溴-2,2'-二硝基联苯 在 lithium aluminium tetrahydride 、 palladium diacetate 、 sodium carbonate 作用下， 以 乙醚 、 N,N-二甲基乙酰胺 、 苯 为溶剂， 反应 10.75h， 生成 3,8-dicyanobenzo[c]cinnoline
  参考文献：
  名称：

  Investigations on the electrochemical properties of new conjugated polymers containing benzo[c]cinnoline and oxadiazole moieties

  摘要：

  A four-step route was designed to synthesize 3,8-benzo[c]cinnoline dicarboxylic acid (4). New conjugated polymers, POXD (I) and POXD (T), containing benzo[c]cinnoline and oxadiazole moieties, were obtained by thermal cyclodehydration of their soluble polyhydrazide precursors PHA (I) and PHA (T), respectively. Two reduction peaks were observed for these new conjugated polymers during CV cathodic scan. From the CV voltammograms combined with the results from molecular simulation, we concluded that the first reduction occurred at oxadiazole moiety and benzo[c]cinnoline moiety was responsible for the second reduction. It indicates that oxadiazole has stronger electron affinity than benzo[c]cinnoline. We proposed a mechanism to explain this two-stage reduction process. Due to the planar and electron-accepting ability of benzo[c]cinnoline and oxadiazole moieties, POXD (I) and POXD (T) exhibited very low LUMO (-3.42 and -3.45 eV) and HOMO (-6.23 and -6.27 eV) energy levels. They can be used as hole-blocking or electron-injection layers for OLED applications. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.10.059

文献信息

• Synthesis and properties of air-stable n-channel semiconductors based on MEH-PPV derivatives containing benzo[c]cinnoline moieties
  作者：Jyh-Chien Chen、Hsin-Chung Wu、Chi-Jui Chiang、Tuo Chen、Li Xing

  DOI：10.1039/c3tc32505a

  日期：——

  In this study we synthesized three novel poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene] (MEH-PPV) derivatives that differ in terms of their ratios of heterocyclic benzo[c]cinnoline moieties: P50 containing only MEH-PPV/benzo[c]cinnolinevinylene (BZCV) alternating segments and P25 and P10 containing both MEH-PPV/BZCV alternating segments and MEH-PPV block segments. UV-Vis and PL spectra of

  在这项研究中，我们合成了三种新颖的聚[2-甲氧基-5-（2-乙基己基氧基）-1,4-亚苯基亚乙烯基]（MEH-PPV）衍生物，它们的杂环苯并[ c ] cinnoline部分的比例不同：P50仅包含MEH-PPV /苯并[ c ]肉桂基亚乙烯基（BZCV）交替链段，P25和P10包含MEH-PPV / BZCV交替链段和MEH-PPV嵌段链段。UV-Vis和这些聚合物的PL光谱显示的值λ UV最大值和λ PL最大的是范围从440到489和从492到551分别纳米，; 当加入其他苯并[ c]时，这些波长会蓝移] cinnoline部分。我们还观察到了从MEH-PPV / BZCV交替段到MEH-PPV嵌段段的能量转移。P50在其主链中具有交替结构，显示出溶剂变色效应，在非极性溶剂中发出绿光，在极性溶剂中发出黄光。使用循环伏安法测量的这些聚合物的HOMO和LUMO能级分别为-5.11至-5.62和-3