9-(6-methylpyrid-2-yl)anthracene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(6-methylpyrid-2-yl)anthracene
• 英文别名: 2-Anthracen-9-yl-6-methylpyridine；2-anthracen-9-yl-6-methylpyridine
• 化学式: C₂₀H₁₅N
• 分子量: 269.346
• InChiKey: CNEBOBUNKFUTIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-(6-methylpyrid-2-yl)anthracene 、 diethylzinc 、 三氯化硼 在 aluminum (III) chloride 、 2,6-二叔丁基吡啶 、 四丁基氯化铵 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 48.0h， 以88%的产率得到
  参考文献：
  名称：

  B–N Lewis Pair Functionalization of Anthracene: Structural Dynamics, Optoelectronic Properties, and O₂ Sensitization

  摘要：

  The judicial placement of main group elements in conjugated structures is emerging as a key route to novel functional hybrid materials. We demonstrate here that the formation of B-N Lewis pairs at the periphery of anthracene leads to buckling of the backbone while also dramatically lowering the LUMO energy. The resulting BN-substituted contorted poly cyclic aromatic hydrocarbons, show large bathochromic, shifts in the absorption and emission relative to all-carbon analogs. In the presence of light, they rapidly react with O(2 )without the need for, an external photosensitizer, resulting in selective and reversible, formation of the corresponding endoperoxides.

  DOI：

  10.1021/jacs.7b11062
• 作为产物：
  描述：

  9-溴蒽 在 四(三苯基膦)钯 、 potassium acetate 、 palladium diacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 96.0h， 生成 9-(6-methylpyrid-2-yl)anthracene
  参考文献：
  名称：

  B–N Lewis Pair Functionalization of Anthracene: Structural Dynamics, Optoelectronic Properties, and O₂ Sensitization

  摘要：

  The judicial placement of main group elements in conjugated structures is emerging as a key route to novel functional hybrid materials. We demonstrate here that the formation of B-N Lewis pairs at the periphery of anthracene leads to buckling of the backbone while also dramatically lowering the LUMO energy. The resulting BN-substituted contorted poly cyclic aromatic hydrocarbons, show large bathochromic, shifts in the absorption and emission relative to all-carbon analogs. In the presence of light, they rapidly react with O(2 )without the need for, an external photosensitizer, resulting in selective and reversible, formation of the corresponding endoperoxides.

  DOI：

  10.1021/jacs.7b11062

文献信息

• B–N Lewis Pair Functionalization of Anthracene: Structural Dynamics, Optoelectronic Properties, and O₂ Sensitization
  作者：Kanglei Liu、Roger A. Lalancette、Frieder Jäkle

  DOI：10.1021/jacs.7b11062

  日期：2017.12.20

  The judicial placement of main group elements in conjugated structures is emerging as a key route to novel functional hybrid materials. We demonstrate here that the formation of B-N Lewis pairs at the periphery of anthracene leads to buckling of the backbone while also dramatically lowering the LUMO energy. The resulting BN-substituted contorted poly cyclic aromatic hydrocarbons, show large bathochromic, shifts in the absorption and emission relative to all-carbon analogs. In the presence of light, they rapidly react with O(2 )without the need for, an external photosensitizer, resulting in selective and reversible, formation of the corresponding endoperoxides.