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Spectroscopic properties of p/p and o/o type iron(III)-metal-free porphyrin dimers and their catalysis as Cytochrome P450 model

Department of Chemistry, Shanghai Jiaotong University, Shanghai 200240, People's Republic of China

Corresponding author, Department of Chemistry, Shanghai Jiaotong University, Shanghai 200240, People's Republic of China.

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JIN-WANG HUANG

School of Chemistry and Chemical Engineering, Zhongshan University, Guangzhou 510275, People's Republic of China

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ZHI-ANG ZHU

Department of Chemistry, Nankai University, Tianjin 300071, People's Republic of China

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LIANG-NIAN JI

School of Chemistry and Chemical Engineering, Zhongshan University, Guangzhou 510275, People's Republic of China

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, and

YUN-TI CHEN

Department of Chemistry, Nankai University, Tianjin 300071, People's Republic of China

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https://doi.org/10.1002/jpp.337Cited by:20 (Source: Crossref)

Abstract

Two series of p/p and o/o type iron(III)-metal-free porphyrin dimers were synthesized and characterized. The dimers consist of a ferric porphyrin and a free-base porphyrin, covalently linked with an alkoxy chain -O(CH₂)_nO-(n = 2–10) at the para and ortho position of two phenyl rings. The ferric paramagnetic effect and ring current effect on these dimers were discussed by ¹H NMR study; vibration modes sensitive to the conformations of the dimers were investigated from IR spectra; the electron density and spin state of ferric ion were examined using XPS and EPR spectroscopy. The catalytic activities of p/p and o/o type dimers on the hydroxylation of cyclohexane were studied under mild conditions. As a chemical mimic model of Cyto. P450, these porphyrins exhibit higher catalytic activities than the corresponding monomer FeTPPCl. With increase of the carbon numbers of alkoxy chain, the catalytic activity order of p/p dimers is C2 < C3 < C4 < C5 < C6 > C8 > C10, the corresponding order of o/o dimers is C2 > C4 > C6 > C8 > C10. Catalytic results of dimers are shown to strongly depend on their special conformation equilibrium, which affect the steric hindrance and electron transfer between two porphyrin rings.

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