N,N'-dicyanothieno<2,3-b>-9,10-anthraquinone diimmine | 143746-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-dicyanothieno<2,3-b>-9,10-anthraquinone diimmine
• 英文别名: N,N'-dicyanothieno[2,3-b]-9,10-anthraquinone diimmine；(5-cyanoiminonaphtho[3,2-f][1]benzothiol-10-ylidene)cyanamide
• CAS: 143746-76-3
• 化学式: C₁₈H₈N₄S
• 分子量: 312.354
• InChiKey: JLZZVYRJNZUUGL-UHFFFAOYSA-N

物化性质

• 沸点：
  539.0±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  噻吩-2,3-二甲醛 在 四氯化钛 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 N,N'-dicyanothieno<2,3-b>-9,10-anthraquinone diimmine
  参考文献：
  名称：

  Novel .pi.-extended thiophene-fused electron acceptors for organic metals

  摘要：

  Novel pi-extended thiophene-fused TCNQ-type and DCNQI-type acceptors have been synthesized from the corresponding quinones by reaction with Lehnert's reagent and bis(trimethylsilyl)carbodiimide (BTC), respectively. Additionally, an example of the little-known hybrid TCNQ-DCNQI-type acceptor has also been obtained. The cyclic voltammetric data of the novel acceptors reveal two different behaviors for these molecules. The TCNQ-type derivatives exhibit a two-electron single-wave reduction to the dianion, as confirmed by controlled potential coulometry analysis. The DCNQI-type derivatives display two reduction waves to the corresponding radical anion and dianion. The same behavior is shown by the hybrid TCNQ-DCNQI derivative. The acceptor ability is related to molecular planarity, and a comparative crystallographic study involving TCNQ-type and DCNQI-type derivatives (6a, 7a, and 8a) has been performed.

  DOI：

  10.1021/jo00049a027