4,4'-bis(p-fluorophenyl)-2,2'-bipyridine | 854049-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,4'-bis(p-fluorophenyl)-2,2'-bipyridine
• 英文别名: 4-(4-Fluorophenyl)-2-[4-(4-fluorophenyl)pyridin-2-yl]pyridine
• CAS: 854049-20-0
• 化学式: C₂₂H₁₄F₂N₂
• 分子量: 344.363
• InChiKey: XVBKGZNZBMGAOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 、 4,4'-bis(p-fluorophenyl)-2,2'-bipyridine 、 bis(trifluoromethane)sulfonimide lithium 以 乙二醇二甲醚 为溶剂， 以88.3%的产率得到bis(2-methyl-phenylpyridine)-4,4'-bis(4-fluorophenyl)-2,2'-bipyridine iridium(III) trifluoromethanesulfonimide
  参考文献：
  名称：

  带有TFSI抗衡阴离子的琥珀色发光电化学电池的结构-性能关系：通过N∧N配体上的不同取代基提高装置性能

  摘要：

  合成了琥珀色的新型Ir（III）配合物：[Ir（Meppy）2（Fpbpy）] [PF 6 ]（1b PF 6），[Ir（Meppy）2（Fpbpy）] [TFSI]（1b TFSI）， [Ir（Meppy）2（MeObpy）] [PF 6 ]（2b PF 6）和[Ir（Meppy）2（MeObpy）] [TFSI]（2b TFSI），其中Meppy = 2-（对-甲基苯基）-吡啶（b），Fpbpy ＝ 4，4′-双（4-氟苯基）-2，2′-联吡啶（1），MeObpy ＝ 4，4′-双（4-甲氧基）-2，2′-联吡啶（2个）。光物理和X射线结果表明，该配合物具有聚集诱导的磷光发射（AIPE）和盐诱导的多态性效应。与固态的其他配合物相比，在配合物2b TFSI中观察到最高的光致发光强度。通过使用具有B3LYP和PBE0杂合功能的双和三ζ基集，还研究了它们在乙腈中的理论吸收和磷光发射跃迁。复杂的2b

  DOI：

  10.1021/acs.inorgchem.0c02939
• 作为产物：
  描述：

  4,4'-二溴-2,2'-联吡啶1,1'-二氧化物 在 三溴化磷 、 sodium carbonate 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 18.25h， 生成 4,4'-bis(p-fluorophenyl)-2,2'-bipyridine
  参考文献：
  名称：

  Electronic Optimization of Heteroleptic Ru(II) Bipyridine Complexes by Remote Substituents: Synthesis, Characterization, and Application to Dye-Sensitized Solar Cells

  摘要：

  We prepared a series of new heteroleptic ruthenium(II) complexes, Ru(NCS)(2)LL' (3a-3e), where L is 4,4'-di(hydroxycarbonyl)-2,2'-bipyridine and L' is 4,4'-di(p-X-phenyl)-2,2'-pyridine (x = CN (a), F (b), H (c), OMe (d), and NMe2 (e)), in an attempt to explore the structure activity relationships in their photophysical and electrochemical behavior and in their performance in dye-sensitized solar cells (DSSCs). When substituent X is changed from electron-donating NMe2 to electron-withdrawing CN, the absorption and emission maxima reveal systematic bathochromic shifts. The redox potentials of these dyes are also significantly influenced by X. The electronic properties of the dyes were theoretically analyzed using density functional theory calculations; the results show good correlations with the experimental results. The solar-cell performance of DSSCs based on dye-grafted nanocrystalline TiO2 using 3a-3e and standard N3 (bis[(4,4'-carboxy-2,2'-bipyridine)(thiocyanato)]ruthenium(II)) were compared, revealing substantial dependences on the dye structures, particularly on the remote substituent X. The 3d-based device showed the best performance: eta = 8.30%, J(SC) = 16.0 mA center dot cm(-2), V-OC = 717 mV, and ff = 0.72. These values are better than N3-based device.

  DOI：

  10.1021/ic101909e

文献信息

• Luminescent lanthanide complexes with imine ligands and devices made with such complexes
  申请人：——

  公开号：US20030129450A1

  公开（公告）日：2003-07-10

  The present invention is generally directed to luminescent lanthanide compounds with imine ligands, and devices that are made with the lanthanide compounds.

  本发明一般涉及带有亚胺配体的发光镧系化合物，以及用这些镧系化合物制造的装置。
• LUMINESCENT LANTHANIDE COMPLEXES WITH IMINE LIGANDS AND DEVICES MADE WITH SUCH COMPLEXES
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP1406909A1

  公开（公告）日：2004-04-14
• PYRIDINE AND PYRIMIDINE DERIVATIVES AS MGLUR2 ANTAGONISTS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2001849B1

  公开（公告）日：2014-11-26
• [EN] LUMINESCENT LANTHANIDE COMPLEXES WITH IMINE LIGANDS AND DEVICES MADE WITH SUCH COMPLEXES<br/>[FR] COMPLEXES DE LANTHANIDE LUMINESCENTS AVEC LIGANDS IMINE ET DISPOSITIFS FABRIQUES A L'AIDE DE TELS COMPLEXES
  申请人：DU PONT

  公开号：WO2003008424A1

  公开（公告）日：2003-01-30

  The present invention is generally directed to luminescent lanthanide compounds with imine ligands, and devices that are made with the lanthanide compounds.
• Electronic Optimization of Heteroleptic Ru(II) Bipyridine Complexes by Remote Substituents: Synthesis, Characterization, and Application to Dye-Sensitized Solar Cells
  作者：Won-Sik Han、Jung-Kyu Han、Hyun-Young Kim、Mi Jin Choi、Yong-Soo Kang、Chyongjin Pac、Sang Ook Kang

  DOI：10.1021/ic101909e

  日期：2011.4.18

  We prepared a series of new heteroleptic ruthenium(II) complexes, Ru(NCS)(2)LL' (3a-3e), where L is 4,4'-di(hydroxycarbonyl)-2,2'-bipyridine and L' is 4,4'-di(p-X-phenyl)-2,2'-pyridine (x = CN (a), F (b), H (c), OMe (d), and NMe2 (e)), in an attempt to explore the structure activity relationships in their photophysical and electrochemical behavior and in their performance in dye-sensitized solar cells (DSSCs). When substituent X is changed from electron-donating NMe2 to electron-withdrawing CN, the absorption and emission maxima reveal systematic bathochromic shifts. The redox potentials of these dyes are also significantly influenced by X. The electronic properties of the dyes were theoretically analyzed using density functional theory calculations; the results show good correlations with the experimental results. The solar-cell performance of DSSCs based on dye-grafted nanocrystalline TiO2 using 3a-3e and standard N3 (bis[(4,4'-carboxy-2,2'-bipyridine)(thiocyanato)]ruthenium(II)) were compared, revealing substantial dependences on the dye structures, particularly on the remote substituent X. The 3d-based device showed the best performance: eta = 8.30%, J(SC) = 16.0 mA center dot cm(-2), V-OC = 717 mV, and ff = 0.72. These values are better than N3-based device.