9-N-ethylamino-1-oxo-phenalene | 344315-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 非那烯类
• 英文名称: 9-N-ethylamino-1-oxo-phenalene
• 英文别名: 9-(Ethylamino)phenalen-1-one；9-(ethylamino)phenalen-1-one
• CAS: 344315-54-4
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: KDYCKTDQYDNDAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-N-ethylamino-1-oxo-phenalene 在 四氯化硅 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 tris(9-N-ethylamino-1-oxo-phenalene)silicon chloride
  参考文献：
  名称：

  三苯萘基中性自由基分子导体

  摘要：

  我们报告了三（1,9-二取代苯基）硅中性自由基新家族第一个成员的制备、结晶和固态表征。在固态下，自由基以弱的部分 pi-二聚体形式与分子间碳......碳接触，落在范德华原子分离处。磁化率测量表明，从室温到 50 K，每个分子大约有 0.7 个居里自旋，低于这个温度，反铁磁耦合变得明显；该化合物的室温单晶电导率为 sigmaRT = 2.4 x 10(-6) S cm(-1)。

  DOI：

  10.1021/ja077771o
• 作为产物：
  描述：

  9-羟基-萘嵌苯-1-酮 、 乙胺 以 水 为溶剂， 反应 2.0h， 以82%的产率得到9-N-ethylamino-1-oxo-phenalene
  参考文献：
  名称：

  Dimeric Phenalenyl-Based Neutral Radical Molecular Conductors

  摘要：

  We report the preparation, crystallization, and solid-state characterization of ethyl (3)- and butyl (4)-substituted spiro-biphenalenyl radicals. Both of these compounds are found to be conducting face-to-face pi -dimers in the solid state but with different room-temperature magnetic ground states. At room temperature, 4 exists as a diamagnetic is-dimer (interplanar separation of similar to3.1 Angstrom), whereas 3 is a paramagnetic pi -dimer (interplanar separation of .similar to3.3 Angstrom), and both compounds show phase transitions between the paramagnetic and diamagnetic forms. Electrical resistivity measurements of single crystals of 3 and 4 show that the transition from the high-temperature paramagnetic pi -dimer form to the low-temperature diamagnetic pi -dimer structure is accompanied by an increase in conductivity by about 2 orders of magnitude. This behavior is unprecedented and is very difficult to reconcile with the usual understanding of a Peierls dimerization, which inevitably leads to an insulating ground state. We tentatively assign the enhancement in the conductivity to a decrease in the on-site Coulombic correlation energy (U), as the dimers form a super-molecule with twice the amount of conjugation.

  DOI：

  10.1021/ja0039785

文献信息

• Dimeric Phenalenyl-Based Neutral Radical Molecular Conductors
  作者：X. Chi、M. E. Itkis、K. Kirschbaum、A. A. Pinkerton、R. T. Oakley、A. W. Cordes、R. C. Haddon

  DOI：10.1021/ja0039785

  日期：2001.5.1

  We report the preparation, crystallization, and solid-state characterization of ethyl (3)- and butyl (4)-substituted spiro-biphenalenyl radicals. Both of these compounds are found to be conducting face-to-face pi -dimers in the solid state but with different room-temperature magnetic ground states. At room temperature, 4 exists as a diamagnetic is-dimer (interplanar separation of similar to3.1 Angstrom), whereas 3 is a paramagnetic pi -dimer (interplanar separation of .similar to3.3 Angstrom), and both compounds show phase transitions between the paramagnetic and diamagnetic forms. Electrical resistivity measurements of single crystals of 3 and 4 show that the transition from the high-temperature paramagnetic pi -dimer form to the low-temperature diamagnetic pi -dimer structure is accompanied by an increase in conductivity by about 2 orders of magnitude. This behavior is unprecedented and is very difficult to reconcile with the usual understanding of a Peierls dimerization, which inevitably leads to an insulating ground state. We tentatively assign the enhancement in the conductivity to a decrease in the on-site Coulombic correlation energy (U), as the dimers form a super-molecule with twice the amount of conjugation.
• Trisphenalenyl-Based Neutral Radical Molecular Conductor
  作者：Sushanta K. Pal、Mikhail E. Itkis、Fook S. Tham、Robert W. Reed、Richard T. Oakley、Robert C. Haddon

  DOI：10.1021/ja077771o

  日期：2008.3.1

  We report the preparation, crystallization, and solid-state characterization of the first member of a new family of tris(1,9-disubstituted phenalenyl)silicon neutral radicals. In the solid state, the radical packs as weak partial pi-dimers with intermolecular carbon...carbon contacts that fall at the van der Waals atomic separation. Magnetic susceptibility measurements indicate approximately 0.7 Curie

  我们报告了三（1,9-二取代苯基）硅中性自由基新家族第一个成员的制备、结晶和固态表征。在固态下，自由基以弱的部分 pi-二聚体形式与分子间碳......碳接触，落在范德华原子分离处。磁化率测量表明，从室温到 50 K，每个分子大约有 0.7 个居里自旋，低于这个温度，反铁磁耦合变得明显；该化合物的室温单晶电导率为 sigmaRT = 2.4 x 10(-6) S cm(-1)。