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Synthesis, Characterization and Spectral Properties of Substituted Tetraphenylporphyrin Iron Chloride Complexes

A series of substituted tetraphenylporphyrin iron chloride complexes [RTPPFe(III)Cl, R=o/p-NO(2), o/p-Cl, H, o/p-CH(3), o/p-OCH(3)] were synthesized by a novel universal mixed-solvent method and the spectral properties of free base porphyrins and iron porphyrin compounds were compared with each othe...

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Autores principales: Sun, Zhi-Cheng, She, Yuan-Bin, Zhou, Yang, Song, Xu-Feng, Li, Kai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6260636/
https://www.ncbi.nlm.nih.gov/pubmed/21471935
http://dx.doi.org/10.3390/molecules16042960
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author Sun, Zhi-Cheng
She, Yuan-Bin
Zhou, Yang
Song, Xu-Feng
Li, Kai
author_facet Sun, Zhi-Cheng
She, Yuan-Bin
Zhou, Yang
Song, Xu-Feng
Li, Kai
author_sort Sun, Zhi-Cheng
collection PubMed
description A series of substituted tetraphenylporphyrin iron chloride complexes [RTPPFe(III)Cl, R=o/p-NO(2), o/p-Cl, H, o/p-CH(3), o/p-OCH(3)] were synthesized by a novel universal mixed-solvent method and the spectral properties of free base porphyrins and iron porphyrin compounds were compared with each other. The experimental results showed that the one-pot mixed solvent method was superior to the two-step method in the yields, reaction time and workup of reaction mixtures for the synthesis of iron porphyrin compounds. The highest yields (28.7%–40.4%) of RTPPFe(III)Cl were obtained in the mixed solvents propionic acid, glacial acetic acid and m-nitrotoluene under reflux for 2 h. A detailed analysis of ultraviolet-visible (UV-vis), infrared (IR) and far-infrared (FIR) spectra suggested the transformation from free base porphyrins to iron porphyrins. The red shift of the Soret band in ultraviolet-visible spectra due to the presence of p-nitrophenyl substituents and the blue shift of Fe-Cl bond of TPPFeCl in far-infrared spectra were further explained by the electron transfer and molecular planarity in the porphyrin ring.
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spelling pubmed-62606362018-12-10 Synthesis, Characterization and Spectral Properties of Substituted Tetraphenylporphyrin Iron Chloride Complexes Sun, Zhi-Cheng She, Yuan-Bin Zhou, Yang Song, Xu-Feng Li, Kai Molecules Article A series of substituted tetraphenylporphyrin iron chloride complexes [RTPPFe(III)Cl, R=o/p-NO(2), o/p-Cl, H, o/p-CH(3), o/p-OCH(3)] were synthesized by a novel universal mixed-solvent method and the spectral properties of free base porphyrins and iron porphyrin compounds were compared with each other. The experimental results showed that the one-pot mixed solvent method was superior to the two-step method in the yields, reaction time and workup of reaction mixtures for the synthesis of iron porphyrin compounds. The highest yields (28.7%–40.4%) of RTPPFe(III)Cl were obtained in the mixed solvents propionic acid, glacial acetic acid and m-nitrotoluene under reflux for 2 h. A detailed analysis of ultraviolet-visible (UV-vis), infrared (IR) and far-infrared (FIR) spectra suggested the transformation from free base porphyrins to iron porphyrins. The red shift of the Soret band in ultraviolet-visible spectra due to the presence of p-nitrophenyl substituents and the blue shift of Fe-Cl bond of TPPFeCl in far-infrared spectra were further explained by the electron transfer and molecular planarity in the porphyrin ring. MDPI 2011-04-06 /pmc/articles/PMC6260636/ /pubmed/21471935 http://dx.doi.org/10.3390/molecules16042960 Text en © 2011 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Sun, Zhi-Cheng
She, Yuan-Bin
Zhou, Yang
Song, Xu-Feng
Li, Kai
Synthesis, Characterization and Spectral Properties of Substituted Tetraphenylporphyrin Iron Chloride Complexes
title Synthesis, Characterization and Spectral Properties of Substituted Tetraphenylporphyrin Iron Chloride Complexes
title_full Synthesis, Characterization and Spectral Properties of Substituted Tetraphenylporphyrin Iron Chloride Complexes
title_fullStr Synthesis, Characterization and Spectral Properties of Substituted Tetraphenylporphyrin Iron Chloride Complexes
title_full_unstemmed Synthesis, Characterization and Spectral Properties of Substituted Tetraphenylporphyrin Iron Chloride Complexes
title_short Synthesis, Characterization and Spectral Properties of Substituted Tetraphenylporphyrin Iron Chloride Complexes
title_sort synthesis, characterization and spectral properties of substituted tetraphenylporphyrin iron chloride complexes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6260636/
https://www.ncbi.nlm.nih.gov/pubmed/21471935
http://dx.doi.org/10.3390/molecules16042960
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