10-phenylphenanthrene-9-carbonitrile | 855603-79-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 10-phenylphenanthrene-9-carbonitrile
• CAS: 855603-79-1
• 化学式: C₂₁H₁₃N
• 分子量: 279.341
• InChiKey: KXFUBAAAFSQPRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 10-phenylphenanthrene-9-carbonitrile 在 乙醚 、 苯 作用下， 生成 1-(10-phenyl-[9]phenanthryl)-ethanone-imine
  参考文献：
  名称：

  Aromatic Cyclodehydration. XXIII.¹ Phenanthrene Derivatives by the Cyclization of Keto Nitriles

  摘要：

  DOI：

  10.1021/ja01157a074
• 作为产物：
  描述：

  三苯基丙烯腈 生成 10-phenylphenanthrene-9-carbonitrile
  参考文献：
  名称：

  Exploration of Highly Efficient Blue–Violet Light Conversion Agents for an Agricultural Film Based on Structure Optimization of Triphenylacrylonitrile

  摘要：

  To obtain highly efficient blue-violet light conversion agents used for an agricultural film, six triarylacrylonitrile derivatives and their doping films were prepared. Further, the luminogens have the ability to convert ultraviolet light into blue-violet light and exhibit aggregation-dependent fluorescence emission and high-contrast fluorescence quantum yields from 0.004 to 0.833. On the basis of X-ray single-crystal diffraction analysis and aggregation-induced emission activity tests, the variant fluorescence quantum yields are attributed to intermolecular pi-pi stacking and phase transition between the crystalline state and amorphous state. In a simulated greenhouse environment, the luminogens exhibit excellent photostability. However, their fluorescence intensity drops to 17-40% of the prime intensity after outdoor radiation for 1 month as a result of the ring-closing oxidation reaction (in the summer). By comprehensively considering the above photophysical properties and mechanical properties of the doping film, 2-([1,1'-biphenyl]-4-yl)-3,3-diphenylacrylonitrile is a potential light conversion agent for an agricultural film in the winter. More importantly, the results indicate that the properties of the light conversion films are expected to be further improved by molecular design, inhibiting the ring-closing oxidation reaction and dispersion of crystalline nanoparticles in the doping film.

  DOI：

  10.1021/acs.jafc.8b05453

文献信息

• Direct synthesis of phenanthrenyl triflates from 1-biphenylyl-2-diazo-2-aryl ketones and triflic anhydride
  作者：Yueqiang Liu、Sheng Zhang、Xiujuan Feng、Xiaoqiang Yu、Yoshinori Yamamoto、Ming Bao

  DOI：10.1039/d3ob02005c

  日期：——

  A strategy for direct synthesis of phenanthrenyl triflates from 1-biphenylyl-2-diazo-2-aryl ketones and triflic anhydride is described. The reaction of 1-biphenylyl-2-diazo-2-aryl ketones with triflic anhydride proceeded smoothly in the presence of 2,6-di-tert-butylpyridine under mild conditions to produce phenanthrenyl triflates in high to excellent yields. The phenanthrenyl triflate products were

  描述了从 1-联苯基-2-重氮-2-芳基酮和三氟甲磺酸酐直接合成菲基三氟甲磺酸酯的策略。 1-联苯基-2-重氮-2-芳基酮与三氟甲磺酸酐的反应在2,6-二叔丁基吡啶存在下在温和条件下顺利进行，以高至优异的产率生成菲基三氟甲磺酸酯。菲基三氟甲磺酸酯产品被证明可用作各种偶联反应中的偶联配偶体。所提出的机制涉及原位形成的乙烯基阳离子中间体的分子内弗里德尔-克来福特反应。