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Molecules 2011, 16(4), 2960-2970; doi:10.3390/molecules16042960
Article

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

, * , ,  and
Institute of Green Chemistry and Fine Chemicals, Beijing University of Technology, Beijing 100124, China
* Author to whom correspondence should be addressed.
Received: 22 February 2011 / Revised: 23 March 2011 / Accepted: 31 March 2011 / Published: 6 April 2011
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Abstract

A series of substituted tetraphenylporphyrin iron chloride complexes [RTPPFe(III)Cl, R=o/p-NO2, o/p-Cl, H, o/p-CH3, o/p-OCH3] 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.
Keywords: synthesis; porphyrin; iron porphyrin; spectra property   synthesis; porphyrin; iron porphyrin; spectra property  
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Sun, Z.-C.; She, Y.-B.; Zhou, Y.; Song, X.-F.; Li, K. Synthesis, Characterization and Spectral Properties of Substituted Tetraphenylporphyrin Iron Chloride Complexes. Molecules 2011, 16, 2960-2970.

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