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Sci. Pharm. 2010, 78(4), 767-790; doi:10.3797/scipharm.1003-13

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

1
Laboratorio de Fotoquímica, Centro de Química, Instituto Venezolano de Insvestigaciones Científicas, I.V.I.C., Apartado 21827, Caracas 1020-A, Venezuela
2
Universidad de Carabobo, Facultad Experimental de Ciencia y Tecnología, Escuela de Química, Valencia, Edo. Carabobo, Venezuela
*
Author to whom correspondence should be addressed.
Received: 16 March 2010 / Accepted: 6 August 2010 / Published: 7 August 2010
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Abstract

The synthesis of the meso-tetra(pyren-1-yl)porphyrin (1) was successfully accomplished by means of the pyrrole condensation with pyrene-1-carbaldehyde 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 14 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.
Keywords: Pyrenylporphyrin; Singlet oxygen; Fluorescence; Photo-oxidation Pyrenylporphyrin; Singlet oxygen; Fluorescence; Photo-oxidation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

ZOLTAN, T.; VARGAS, F.; RIVAS, C.; LÓPEZ, V.; PEREZ, J.; BIASUTTO, A. Synthesis, Photochemical and Photoinduced Antibacterial Activity Studies of meso-Tetra(pyren-1-yl)porphyrin and its Ni, Cu and Zn Complexes. Sci. Pharm. 2010, 78, 767-790.

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