Citation: HU Yu-Qiang, ZHU Ning, HAN Li-Min. Channel of Electronic Interactions in Diferrocenyl Pyrrole Derivatives[J]. Acta Physico-Chimica Sinica, ;2015, 31(2): 227-236. doi: 10.3866/PKU.WHXB201411061 shu

Channel of Electronic Interactions in Diferrocenyl Pyrrole Derivatives

1.
College of Chemical Engineering, Inner Mon lia University of Technology, Hohhot 010051, P. R. China

Received Date: 5 August 2014
Available Online: 6 November 2014
Fund Project: 内蒙古自治区自然科学基金(2012ZD01) (2012ZD01) 内蒙古工业大学自然科学基金(X201207) (X201207)内蒙古自治区研究生科研创新基金(B20131012802)资助项目 (B20131012802)

2,5-Diferrocenyl-1-(3-trifluorom-ethylphenyl)-pyrrole (1), 2,5-diferrocenyl-1-(4-fluorophenyl)-pyrrole (2), 2,5-diferrocenyl-1-phenyl pyrrole (3), 2,5-diferro-cenyl-1-(4-ethylphenyl)-pyrrole (4), and 2,5-diferrocenyl- 1-(4-ethoxyphenyl)-pyrrole (5) were prepared by the one-pot cycloaddition reaction of ferrocenyl alkyne. The 2,5-diferrocenyl-1-phenyl-1-pyrrole derivatives were characterized by elemental analysis, Fourier-transform infrared (FTIR) spectroscopy, mass spectrometry (MS), and nuclear magnetic resonance (NMR) spectroscopy. The influence of substituents at the phenyl moiety on the electronic interaction was studied using cyclic voltammetry (CV) and density functional theory (DFT) calculations. A linear relationship was observed between the first oxidation potential (E_a1), oxidation potential difference (ΔE) with Hammett constant (Hammett σ) of the substituent, pyrrole ¹H NMR chemical shift (δ), and pyrrole N natural bond orbital (NBO) charge. A high N charge density weakened the electronic interaction, and vice versa. Electron transfer between the two ferrocenyl units of these diferrocenyl pyrrole derivatives was influenced by the N charge density.
- Diferrocenyl,
- Pyrrole derivative,
- Channel of electronic interaction
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