3,8-Bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-1,10-phenanthroline | 1403267-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 3,8-Bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-1,10-phenanthroline
• 英文别名: 3,8-bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-1,10-phenanthroline
• CAS: 1403267-89-9
• 化学式: C₂₀H₆F₁₈N₂
• 分子量: 616.252
• InChiKey: ASLDLUOQDSGIMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  3,8-二溴菲罗啉 、 全氟碘代丁烷 在 铜 作用下， 以 二甲基亚砜 为溶剂， 生成 3,8-Bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-1,10-phenanthroline
  参考文献：
  名称：

  Strengthening π–π Interactions While Suppressing C_sp2–H···π (T-Shaped) Interactions via Perfluoroalkylation: A Crystallographic and Computational Study That Supports the Beneficial Formation of 1-D π–π Stacked Aromatic Materials

  摘要：

  The design and synthesis of aromatic crystalline materials with controllable crystal structure packing is of particular interest in organic semiconductor and optoelectronic devices, where 1-D pi-pi stacked structures that enhance charge mobility are the most beneficial. We report here that the pi-pi interactions between aromatic molecules can be strengthened and the C-sp2-H center dot center dot center dot pi (T-shape) interaction can be suppressed by perfluoroalkylation of corresponding aromatics. Both crystal structure data and ab initio calculations show that the pi-pi interaction is strengthened due to the electronic effects of perfluoroalkyl substituents, and the C-sp2-H center dot center dot center dot pi interaction is suppressed by the steric effects of the perfluoroalkyl substituents. The C-sp3-F center dot center dot center dot F-C-sp3 attractive interactions between perfluoroalkyl chains further stabilize the crystal structures. We also found that C-sp3-F center dot center dot center dot pi interaction can be eliminated if an optimal electron deficiency of the pi system is tuned by adjusting the number of perfluoroalkyl substituents. The insight gained from this study is of particular interest in organic semiconductor research as well as the fields of molecular recognition, sensing, and design of enzyme inhibitors where pi-pi interactions are also important.

  DOI：

  10.1021/cg301151u