Two novel magnesium(II) meso-tetraphenylporphyrin-based coordination complexes: Syntheses, combined experimental and theoretical structures elucidation, spectroscopy, photophysical properties and antibacterial activity

Abstract

Two novel magnesium(II) tetraphenylporphyrin-based six-coordinate complexes; bis(hexamethylenetetramine)(5,10,15,2O tetrakis[4(benzoyloxy)phenyl]porphinato) magnesuim(II) (1) and bis(1,4-diazabicyclo(2.2.2)octane) (5,10,15,2O-tetrakis[4-(benzoyloxy)phenyl]porphinato)magnesium(II) (2) have been synthesised and confirmed by proton nuclear magnetic resonance, mass spectrometry, elemental analysis and IR spectroscopy. Both crystal structures were determined and described by single crystal X-ray diffraction analysis and Hirshfeld surfaces computational method. All Mg(II) atoms are surrounded by four porphyrin nitrogen atoms and two axial ligands coordinated to the metal ion through one nitrogen atom, forming a regular octahedron. In both complexes, molecular structures and three-dimensional framework are stabilised by inter-and intramolecular C-HO and C-HN hydrogen bonds, and by weak C-HCg π interactions. UV-visible and Fluorescence investigations, respectively, show that studied complexes have a strong absorption in red part and exhibit an emission in the blue region. The HOMO-LUMO energy gap values, modelled using the DFT approach, indicates that both studied compounds can be classified as semiconductors. The role of these complexes as novel antibacterial agents was also performed.

A new cobalt(ii)meso-porphyrin: synthesis, characterization, electric properties and application in the catalytic degradation of dyes

“…Our compounds are in general agreement with those recently reported for a number of porphyrins. 19,28 The 2897 and 2923 cm À1 peaks are associated with antisymmetric and symmetric alkyl C-H vibrations. The strongest absorption peaks in the spectra at 1736 and 1260 cm À1 can be associated with the ester group stretch.…”

“…The E g-op values were 1.85 eV (l gap ¼ 670 nm) for H 2 TMAPP and 2.18 eV (l gap ¼ 568 nm) for [Co II (TMAPP)], which are in the normal range of meso-porphyrins and magnesium metalloporphyrins. 19,33,34 Steady-state emission spectroscopy. The room temperature uorescence spectra in dichloromethane (10 À6 mol L À1 ) are shown in Fig.…”

“…17 Recently, our research group managed to design and characterize new metalloporphyrinbased materials. [18][19][20] In this paper, and in continuation of our work on the functionalization of meso tetra-arylporphyrins, we have synthesised a new porphyrin, H 2 TMAPP (1) (TMAPP ¼ 5,10,15,20-tetrakis{4-[((4-methoxyphenyl)acetyl)oxy]phenyl} porphyrin), and its cobalt complex [Co II (TMAPP)] (2), which are substituted at the meso position by ester groups comprising two benzene rings plus methoxy functions (Scheme 1). With this aim, our compounds have been characterized by infrared, proton nuclear magnetic resonance spectroscopy, mass spectrometry, and elemental analysis.…”

New DMAP meso-arylporphyrin Magnesium(II) complex. Spectroscopic, Cyclic voltammetry and X-ray molecular structure characterization. DFT, DOS and MEP calculations and Antioxidant and Antifungal activities

“…Moreover, the past decade has witnessed intense research devoted to the antioxidant, antibacterial and antifungal activities of porphyrin species [17][18][19][20][21][22]. It should also be noted that our research group has published in recent years a number of works on the use of magnesium(II) porphyrin complexes as antibacterial agents [23,24].…”

Syntheses, crystal structures, photo-physical properties, antioxidant and antifungal activities of Mg(II) 4,4′-bipyridine and Mg(II) pyrazine complexes of the 5,10,15,20 tetrakis(4–bromophenyl)porphyrin

“…Interestingly, Mg(II) porphyrin can easily bind with N/O-donor ligands to produce both five-and six-coordinate complexes [30][31][32][33][34]. Recently, we also reported the preparation of one magnesium derivatives [Mg(TBrPP)(HIm)] five-coordinate [35] and two sixcoordinate magnesium complexes [Mg(TPBP)(L)2] (TPBP = 5,10,15,20-tetrakis[4(benzoyloxy)phenyl]porphyrin and L = Hexamethylenetetramine -HTMA-or 1,4-diazabicyclo[2.2.2]octane -DABCO-) [36]. In this context, it was pointed out that these complexes possess interesting activities against several bacterial species including Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Pseudomonas aeruginosa.…”