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

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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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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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