1,3-bis(1H,1H,2H,2H-perfluorooctyl)imidazolium iodide | 197712-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-bis(1H,1H,2H,2H-perfluorooctyl)imidazolium iodide
• 英文别名: 1,3-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazolium iodide；1,3-bis(1H,1H,2H,2H-pentafluorooctyl)imidazolium iodide；1,3-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazol-1-ium;iodide
• CAS: 197712-82-6
• 化学式: C₁₉H₁₁F₂₆N₂*I
• 分子量: 888.173
• InChiKey: KBIBHBWLDRYAJP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  48.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  8.81
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,3-bis(1H,1H,2H,2H-perfluorooctyl)imidazolium iodide 在 hydroxide-loaded ion exchange Lewatit Mono MP Plus 800 resin 作用下， 以 甲醇 、 水 为溶剂， 生成 1,3-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazolium perfluorododecanoate
  参考文献：
  名称：

  全氟吡啶鎓和咪唑鎓离子液体

  摘要：

  制备具有全氟化侧链的离子液体作为表面浸渍的混合材料。对于阳离子部分，使用甲基和乙基吡啶鎓以及咪唑鎓支架。阴离子是氢氧根、乙酸根、三氟乙酸根、三氟甲磺酸根、三氟甲磺酸根、氯离子、溴离子、碘离子、硫酸氢根和全氟十二酸根。该研究的主要特征是作为盐的氟化部分的全氟己基残基相对较短，由于其较低的生物累积性，使目标化合物成为既定产品的有益替代品。一种化合物产生了适用于 X 射线结构分析的单晶，揭示了分层结构，具有相对良好解析的硬离子域与无序的软全氟化层交替。通过测量玻璃表面上的薄膜的水接触角来研究所有 30 种材料的润湿性。在两种情况下，观察到有希望的接触角（130° 和 140°），表明该产品可能是表面浸渍的合适候选者。

  DOI：

  10.1002/ejoc.201700717
• 作为产物：
  描述：

  1-碘-1H,1H,2H,2H-全氟辛烷 以 乙酸乙酯 、 甲苯 为溶剂， 生成 1,3-bis(1H,1H,2H,2H-perfluorooctyl)imidazolium iodide
  参考文献：
  名称：

  Fluoroalkylated N-heterocyclic carbene complexes of palladium

  摘要：

  Fluoroalkylated N-heterocyclic carbene complexes of palladium have been synthesized from imidazolium salts and Pd(OAc)(2). The analogous carbene complexes bearing long alkyl chains have also been prepared. The formation of these carbene complexes proceeds via an intermediate binuclear species, which has been isolated. Complexes such as these may find applications in catalysis in supercritical CO2 (scCO(2)). (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00008-5

文献信息

• A novel system for the Suzuki cross-coupling reaction catalysed with light fluorous palladium–NHC complex
  作者：Hong Yu、Li Wan、Chun Cai

  DOI：10.1016/j.jfluchem.2012.08.005

  日期：2012.12

  A novel Pd-NHC catalyst containing fluorous tags was synthesized and characterized. The catalytic activity and stability of the catalyst has been evaluated for the Suzuki cross-coupling reaction of aryl halides and aryl boronic acids in the mixture solvent of C6F6 and EtOH to afford the corresponding products in excellent yields. In addition, the catalyst can be reused three times without obvious loss of catalytic activity. The structure of the catalyst was characterized by elemental analyses, FT-IR, H-1 NMR, C-13 NMR and F-19 NMR. (C) 2012 Elsevier B.V. All rights reserved.
• Ag Complexes of NHC Ligands Bearing Polyfluoroalkyl and/or Polyfluoropolyalkoxy Ponytails. Why Are Polyethers More Fluorous Than Alkyls?
  作者：Martin Skalický、Veronika Skalická、Jana Paterová、Markéta Rybáčková、Magdalena Kvíčalová、Josef Cvačka、Anna Březinová、Jaroslav Kvíčala

  DOI：10.1021/om201062c

  日期：2012.2.27

  A series of fluorous silver complexes bearing two fluorous NHC ligands was synthesized from bis(polyfluoroallcylated) or bis(polyfluoropolyoxaalkylated) imidazolium salts and silver oxide in acetonitrile. The starting salts were prepared either under conventional conditions in two steps via polyfluoroalkylated imidazoles or preferably directly from imidazole and the respective polyfluoroalkyl triflates or polyfluoropolyoxaalkyl nonaflates bearing a nonfluorinated ethylene or methylene spacer. Surprisingly, striking differences in fluorophilicity were observed for both starting imidazolium salts and target Ag-NHC complexes depending on the type of polyfluorinated chains. While the complexes bearing a polyfluoroalkyl ponytail displayed moderate fluorophilicities f(i), in the range of 0.9-1.8, the presence of fluorinated polyether chains resulted in much higher fluorophilicity reaching for unbranched polyethers values as high as 3.2 with excellent solubility in perfluorinated solvents. For the explanation, DFT calculations on the model imidazolium salts showed that, in contrast to polyfluoroalkyl ponytails pointing out of the imidazolium rings, dominant conformation of the polyfluoropolyether chain is able to shield fluorophobic counteranions against the perfluorinated environment, minimizing thus fluorophobic interactions. We also employed DFT calculations for the confirmation of the higher flexibility of perfluoropolyether chains compared with perfluoroalkyl chains, scanning the energy content of two model compounds, perfluorohexane and perfluoro-3-oxahexane, on their C3-C4 or O-C3 torsion angle.