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

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.

Highly luminescent N-doped carbon quantum dots from lemon juice with porphyrin-like structures surrounded by graphitic network for sensing applications

“…38 In the IR spectra shown in Fig. 1(e), it is observed that aer Fe 3+ sensing, a new peak has been appeared $1000 cm À1 which is due to the Fe-N bond stretching vibration 39 whereas the small decrease in the intensity of the -NH stretching vibration indicates to the successful formation of Fe-N bond. Aer Fe 3+ attachment, shiing in the n-p* transition of the NCQD sample also implies to the interaction of Fe 3+ and NCQD as shown in the UV spectra [ Fig.…”

Self-assembly of iron TCPP (meso-tetra(4-carboxyphenyl)porphyrin) into a chiral 2D coordination polymer

“…The N-H bond stretching and bending frequencies of TCPP located at 3200 cm -1 and 970 cm -1 disappeared when iron ion was inserted into the porphyrin ring, and a characteristic Fe-N band appears at 1000 cm -1 , which indicates the formation of an iron porphyrin compound [39]. The bands at about 3415 cm -1 , 1740 cm -1 and 1200 cm -1 were assigned to the O-H, C=O and C-O bonds of the carboxylic groups, respectively.…”

Synthesis and characterization of some new thallium(III) macrocyclic complexes and their biological studies

“…It is found that the ν(N-H) stretching frequency of free base porphyrins are located at ~3400-3320 cm -1 (Sun et al, 2011) and disappeared when thallium metal ion was inserted into the porphyrin ring. There is an additional Tl-N stretch vibration at 400-500 cm -1 in metalated complexes indicating the formation of Tl(III) porphyrins.…”