双二茂铁基吡咯衍生物电荷交互通道

doi:10.3866/PKU.WHXB201411061

Abstract

Abstract:

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.

Key words: Diferrocenyl, Pyrrole derivative, Channel of electronic interaction

MSC2000:

O646

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HU Yu-Qiang, ZHU Ning, HAN Li-Min. Channel of Electronic Interactions in Diferrocenyl Pyrrole Derivatives[J].Acta Phys. -Chim. Sin., 2015, 31(2): 227-236.

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Channel of Electronic Interactions in Diferrocenyl Pyrrole Derivatives

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