2,5-diferrocenyl-1-phenyl-1H-pyrrole(1+) hexafluorophosphate | 1263048-82-3

• 英文名称: 2,5-diferrocenyl-1-phenyl-1H-pyrrole(1+) hexafluorophosphate
• CAS: 1263048-82-3
• 化学式: C₃₀H₂₅Fe₂N*F₆P
• 分子量: 656.193
• InChiKey: NGSBMABCTVHZIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 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：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  ferrocenium hexafluorophosphate 、 2,5-diferrocenyl-1-phenyl-1H-pyrrole 以 四氢呋喃 为溶剂， 以95%的产率得到2,5-diferrocenyl-1-phenyl-1H-pyrrole(1+) hexafluorophosphate
  参考文献：
  名称：

  Electronically Intercommunicating Iron Centers in Di- and Tetraferrocenyl Pyrroles

  摘要：

  Novel 2,5-diferrocenyl-1-phenyl-1H-pyrrole (4) and 2,3,4,5-tetraferrocenyl-1-phenyl-1H-pyrrole (6) have been prepared by a 2- or 4-fold Negishi cross-coupling reaction of 2,5-dibromo-1-phenyl-1H-pyrrole (3) and 2,3,4,5-tetrabromo-1-phenyl-1H-pyrrole (5), respectively, with FcZnCl (2) (Fc = Fe(eta(5)-C5H4)(eta(5)-C5H5)) in the presence of [(Ph3P)(4)Pd] as catalyst. The electronic and structural properties of 4 and 6 were investigated with UV-vis spectroscopy and single-crystal X-ray diffraction (6). Comparison of the appropriate bond distances in the pyrrole core system of 6 demonstrates considerable electron delocalization. Cyclic, square wave, and linear sweep voltammetry as well as in situ MR spectro-electrochemistry highlight the electrochemical properties of both compounds. Molecules 4 and 6 display two (4) or four (6) electrochemically reversible one-electron transfer processes with remarkably high Delta E-1/2 values and reduction potentials of E-0t = -238 and E-0t = 212 mV for 4 (Delta E-1/2 = 450 mV) and E-0t = 280, E-0t = 51, E-0t = 323, and E-0t = 550 mV for 6 (Delta E-1/2 = 322, 2154, and 233 mV) using [NBu4][B(C6F5)(4)] as the supporting electrolyte. The pyrroles could be classified as class II systems according to Robin and Day. Additionally, 4[PF6](n) (n = 1, 2) were synthesized and studied, giving CV responses and NIR spectra identical to those obtained for 4 from electrochemical oxidations.

  DOI：

  10.1021/om100914m