Synthesis, Photochemical and Photoinduced Antibacterial Activity Studies of meso-Tetra(pyren-1-yl)porphyrin and its Ni, Cu and Zn Complexes

Abstract

The synthesis of the meso-tetra(pyren-1-yl)porphyrin (1) was successfully accomplished by means of the pyrrole condensation with pyrene-1-carb-aldehyde in acidic media. Its metallization was carried out in an almost quantitative yield to obtain the corresponding complexes of Ni(II) (2), Cu(II) (3) and Zn (4). Their photophysical properties such as fluorescence quantum yield and energy transfer to oxygen for an efficient generation of singlet oxygen were determined. Their photophysical and photochemical properties were compared with those of other similar porphyrin derivatives such as tetraphenylporphyrin and tetranaphthylporphyrin. Photochemical studies on their effectiveness as photosensitizer were carried out by means of the photoinduced oxidation of aromatic alcohols like α-naphthol to naphthoquinone. The antibacterial photoactivity assay for compounds 1–4 was testeted against Escherichia coli (ATCC 8739) and its proliferation and viability were measured by chemiluminescence. An efficient inactivation of E. coli was observed. This was more efficient for compounds 2 and 3, following the direct relationship to high generation of singlet oxygen by these compounds.

A Perspective on the Trends and Challenges Facing Porphyrin‐Based Anti‐Microbial Materials

“…An efficient inactivation of E. coli was observed with NiTPyrenP and CuTPyrenP at approximately 70% inactivation at concentrations of 50 μM. The effect was attributed to a direct correlation of singlet oxygen formation by these compounds . In 2014, the same group synthesized and characterized meso ‐tetra‐(4‐benzoate‐9‐phenanthryl)‐porphyrin (TB9FP) and its Zn and Cu complexes.…”

“…Structures of MTPyrenP (M = Ni, Cu, Zn), TB9FP and its corresponding Zn and Cu complexes TB9FPZn and TB9FPCu …”

“…Structures of MTPyrenP (M = Ni, Cu, Zn), TB9FP and its corresponding Zn and Cu complexes TB9FPZn and TB9FPCu. [ 132,133 ] Figure 15. Structures of TPPS 4 , TNPS 4 and TPyEtAcP, and their corresponding Ni(II) and Zn(II) complexes.…”

“…The effect was attributed to a direct correlation of singlet oxygen formation by these compounds. [ 132 ] In 2014, the same group synthesized and characterized meso -tetra-(4-benzoate-9-phenanthryl)-porphyrin (TB9FP) and its Zn and Cu complexes. (Figure 14 ) When the three compounds were irradiated for 15 min in the presence of E. coli at 5 µm mol L −1 , the compounds exhibited relatively strong photoinduced dose-dependent activity, with a tendency of TB9FP > CuTB9FP > ZnTB9FP.…”

Photophysical and photocatalytic behavior of nickel(II) 5,10,15,20-tetrakis(1-methylpyridinium-4-yl)porphyrin

“…This type of metalloporphyrins can be formed with the ions of the iron group, such as Fe(III), Co(III), and Ni(II). However, while the photoredox chemistry of iron(III) and cobalt(III) porphyrins was thoroughly studied in the past 2-3 decades [6,7,8,9,10], the corresponding nickel(II) complexes were hardly examined in this respect [11,12]. Since the complexes of iron(III), cobalt(III) as well as manganese(III) with the cationic 5,10,15,20-tetrakis(1-methylpyridinium-4-yl)porphyrin (H2TMPyP 4+ ) proved to be promising in various photocatalytic systems [3,7,8,13,14,15,16,17], in this work some photophysical and photochemical properties of Ni(II)TMPyP 4+ were studied in order to examin the potential applicability of this metalloporphyrin in utilization of solar radiation in the visible range.…”