N-(4-phenyl-N-(4,4'-bipyridinium))ferrocene nitrate | 1355074-19-9

• 英文名称: N-(4-phenyl-N-(4,4'-bipyridinium))ferrocene nitrate
• CAS: 1355074-19-9
• 化学式: C₂₆H₂₁FeN₂*NO₃
• 分子量: 479.318
• InChiKey: AWRMTXORPSQWDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  六氟磷酸钾 、 N-(4-phenyl-N-(4,4'-bipyridinium))ferrocene nitrate 、 碘甲烷 以 二氯甲烷 、 乙腈 为溶剂， 以60%的产率得到N-(4-ferrocenylphenyl)-N'-methyl-4,4'-bipyridinium bis(hexafluorophosphate)
  参考文献：
  名称：

  Redox Control of Rotary Motions in Ferrocene-Based Elemental Ball Bearings

  摘要：

  Rotational motions of ferrocene-based carousels have been achieved by electron transfer centered on pi-dimerizable 4,4'-bipyridinium substituents introduced on both cyclopentadienyl rings through covalent linkers of different size, geometry, and flexibility. Detailed spectroscopic, electrochemical, and theoretical analyses demonstrate that rigid and fully conjugated linkers allow the quantitative formation of intrarnolecular pi-dimers resulting from optimized orbital overlaps within the HOMO of the electrochemically generated bis-radical species. The tetra-cationic "charge-repelled" conformers, the selfassembled, pi-dimers, and their electron triggered interconversions have been investigated by UV-vis, NMR, and ESR spectroscopy, electrochemistry, X-ray diffraction analysis, and theoretical calculations. These studies support the conclusion that the rotation of both cyclopentadienyl rings in ferrocene can be controlled electrochemically using noncovalent reversible interactions arising from pi-radical coupling processes.

  DOI：

  10.1021/ja209766e
• 作为产物：
  描述：

  4-ferrocenylaniline 、 1-(2,4-dinitrophenyl)-4,4'-bipyridinium chloride 、 potassium nitrate 以 乙醇 、 乙腈 为溶剂， 以90%的产率得到N-(4-phenyl-N-(4,4'-bipyridinium))ferrocene nitrate
  参考文献：
  名称：

  Redox Control of Rotary Motions in Ferrocene-Based Elemental Ball Bearings

  摘要：

  Rotational motions of ferrocene-based carousels have been achieved by electron transfer centered on pi-dimerizable 4,4'-bipyridinium substituents introduced on both cyclopentadienyl rings through covalent linkers of different size, geometry, and flexibility. Detailed spectroscopic, electrochemical, and theoretical analyses demonstrate that rigid and fully conjugated linkers allow the quantitative formation of intrarnolecular pi-dimers resulting from optimized orbital overlaps within the HOMO of the electrochemically generated bis-radical species. The tetra-cationic "charge-repelled" conformers, the selfassembled, pi-dimers, and their electron triggered interconversions have been investigated by UV-vis, NMR, and ESR spectroscopy, electrochemistry, X-ray diffraction analysis, and theoretical calculations. These studies support the conclusion that the rotation of both cyclopentadienyl rings in ferrocene can be controlled electrochemically using noncovalent reversible interactions arising from pi-radical coupling processes.

  DOI：

  10.1021/ja209766e