2-(9-Oxobenzo[f][1]benzothiol-4-ylidene)propanedinitrile | 143773-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(9-Oxobenzo[f][1]benzothiol-4-ylidene)propanedinitrile
• CAS: 143773-89-1
• 化学式: C₁₅H₆N₂OS
• 分子量: 262.291
• InChiKey: KVRWBSNNQYQZEU-UHFFFAOYSA-N

物化性质

• 沸点：
  460.9±45.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二(三甲基硅基)碳酰二亚胺 、 2-(9-Oxobenzo[f][1]benzothiol-4-ylidene)propanedinitrile 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以65%的产率得到N,10,10-tricyanothieno<2,3-b>-1,4-naphthoquinomethane imine
  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
• 作为产物：
  描述：

  naphtho[2,3-b]thiophene-4,9-dione 、 丙二腈 在 吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以26%的产率得到9,9,10,10-tetracyanothieno<2,3-b>-1,4-naphthoquinonedimethane
  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

文献信息

• Novel .pi.-extended thiophene-fused electron acceptors for organic metals
  作者：Pilar De la Cruz、Nazario Martin、Fuencisla Miguel、Carlos Seoane、Armando Albert、Felix H. Cano、Araceli Gonzalez、Jose M. Pingarron

  DOI：10.1021/jo00049a027

  日期：1992.11

  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.