4,4'-bis(HCF2(CF2)3CH2OCH2)-2,2'-bipyridine | 949116-86-3

• 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(HCF2(CF2)3CH2OCH2)-2,2'-bipyridine
• 英文别名: 4,4'-bis(H(CF2)4CH2OCH2)-2,2'-bpy；4-(2,2,3,3,4,4,5,5-Octafluoropentoxymethyl)-2-[4-(2,2,3,3,4,4,5,5-octafluoropentoxymethyl)pyridin-2-yl]pyridine
• CAS: 949116-86-3
• 化学式: C₂₂H₁₆F₁₆N₂O₂
• 分子量: 644.356
• InChiKey: RYQZKAJHOPJECC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  bis(acetonitrile)dichloroplatinum(II) 、 4,4'-bis(HCF2(CF2)3CH2OCH2)-2,2'-bipyridine 以 二氯甲烷 为溶剂， 以94.8%的产率得到[PtCl2(4,4'-bis(HCF2(CF2)3CH2OCH2)-2,2'-bipyridine)]
  参考文献：
  名称：

  Synthesis, structure and spectroelectrochemical property of (2,2′-bipyridine)–metal (M=Pt, Pd) dichloride with 4,4′-bis(fluorous-ponytail) on bipyridine

  摘要：

  The 4,4'-bis(RfCH2OCH2)-2,2'-bpy ligands [R-f = n-C3F7 (1a), HCF2(CF2)(3) (1b)] were prepared and then treated with [MCl2(CH3CN)(2)] (M = Pt or Pd) to result in the corresponding metal complexes, [MCl2(4,4'-bis(RfCH2OCH2)-2,2'-bpy)] (M = Pt 2a-b: Pd 3a-b) Both ligands and metal complexes were fully characterized by multi-nuclei NMR (H-1, F-19 and C-13), FTIR, and mass (GC/MS or HR-FAB) methods. The X-ray structures of 2a-b and 3a-b were studied With terminal CF3, the structures of 2a and 3a exhibit disordered polyfluorinated regions in solid state With terminal HCF2, the structures of 2b and 3b show a it-it stacking of the bpy planes, five-membered C-H O hydrogen bond and all unusual intramolecular blue-shifting C-H F-C hydrogen bond system, whereas without terminal HCF2, the structures of 2a and 3a show the similar pi-pi: stacking, five-membered C-H O hydrogen bond and typical orientation of polyfluorinated ponytails. but not the C-H F-C hydrogen bond system The CV and UV/Vis studies were also carried out (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.poly.2009.12.015

文献信息

• Synthesis, structure and reactivity of novel palladiumdichloride-2,2′-bipyridine with 4,4′-bis(fluorous-ponytail)
  作者：Norman Lu、Yan-Chou Lin、Jeng-Yung Chen、Tsung-Chi Chen、Shih-Chieh Chen、Yuh-Sheng Wen、Ling-Kang Liu

  DOI：10.1016/j.poly.2007.02.009

  日期：2007.8

  showed an almost quantitative conversion and could be reused for eight runs with Heck reactions, in that the products and unspent reactants were directly removed by distillation. With the highest fluorine content in the series, Pd complex 2e was successfully applied in the Heck reaction using the fluorous biphasic catalysis strategy.

  摘要利用现成的氟代链烷醇RfCH2OH，制备了一系列新型的氟马尾混合物bpy配体4,4'-bis（RfCH2OCH2）-2,2'-bpy（1a–e），并用[PdCl2（CH3CN）处理）2]生成相应的新型Pd络合物[PdCl2（4,4'-bis（RfCH2OCH2）-2,2'-bpy）]（2a–e），其中Rf = n-C3F7（a），HCF2（CF2 ）3（b），HCF2（CF2）7（c），n-C8F17（d），n-C10F21（e）。通过多核NMR（1H，19F和13C），FTIR和高分辨率质谱（FAB）对新配体和Pd配合物进行了光谱表征。Pd配合物2b的结构，也是通过单晶X射线衍射研究确定的，其第一个在bpy上具有氟化马尾辫，而在膦上不具有氟化马尾辫。配体和Pd配合物的TGA数据表明，Pd配合物比相应的配体具有更高的耐温性。衍生自2a–c的Pd催化剂显示出几乎定量的转化，可通过Heck
• Novel Fluorous Amphiphilic Heteroleptic Ru-Based Complexes for a Dye-Sensitized Solar Cell: The First Fluorous Bis-ponytailed Amphiphilic Ru Complexes
  作者：Norman Lu、Jia-Sheng Shing、Wen-Han Tu、Ying-Chan Hsu、Jiann T. Lin

  DOI：10.1021/ic102192m

  日期：2011.5.16

  A new series of amphiphilic heteroleptic ruthenium(II) sensitizers with a fluorous bis-ponytailed bipyridine ancillary ligand, [Ru(H2dcbpy)(4,4′-bis(RfCH2OCH2)-2,2′-bpy)(NCS)2] [where Rf = HCF2CF2 (CT4), C3F7 (CT7), and HCF2CF2CF2CF2 (CT8)], have been synthesized and fully characterized by UV/vis, visible emission, NMR, fast atom bombardment mass spectrometry, and cyclic voltammetric studies. Dye-sensitized

  具有氟双桥尾联吡啶辅助配体[Ru（H 2 dcbpy）（4,4'-bis（R f CH 2 OCH 2）-2,2'-bpy ）（NCS）2 ] [其中R f = HCF 2 CF 2（CT4），C 3 F 7（CT7）和HCF 2 CF 2 CF 2 CF 2（CT8））]的合成，并通过紫外/可见光，可见光发射，NMR，快速原子轰击质谱和循环伏安法进行了全面表征。基于这些染料的染料敏化太阳能电池（DSC）的效率可与基于N719的标准电池相比。与无氟双桥尾联吡啶辅助配体的Z907相比，基于CT7或CT8的DSC的转化效率高约9％。发现氟链增加了TiO 2上的染料密度并有助于抑制染料的解吸。