Effects of the Peripheral Substituents, Central Metal, and Solvent on the Photochemical and Photophysical Properties of 5,15-Diazaporphyrins.

Autor: Omomo S; Department of Fundamental Sciences Graduate School of Science and Technology, Niigata University, Nishi-ku, Niigata, 950-2181, Japan., Fukuda R; Department of Biotechnology Graduate School of Engineering, Toyama Prefectural University, Imizu-shi, Toyama, 939-0398, Japan., Miura T; Department of Chemistry Faculty of Science, Niigata University, Nishi-ku, Niigata, 950-2181, Japan., Murakami T; Department of Biotechnology Graduate School of Engineering, Toyama Prefectural University, Imizu-shi, Toyama, 939-0398, Japan.; Institute for Integrated Cell-Material Sciences (iCeMS), Kyoto University Institute for Advanced Study (KUIAS), Sakyo-ku, Kyoto, 606-8501, Japan., Ikoma T; Department of Chemistry Faculty of Science, Niigata University, Nishi-ku, Niigata, 950-2181, Japan.; Center for Coordination of Research Facilities, Niigata University, Nishi-ku, Niigata, 950-2181, Japan., Matano Y; Department of Chemistry Faculty of Science, Niigata University, Nishi-ku, Niigata, 950-2181, Japan.
Jazyk: angličtina
Zdroj: ChemPlusChem [Chempluschem] 2019 Jun; Vol. 84 (6), pp. 740-745. Date of Electronic Publication: 2019 Mar 04.
DOI: 10.1002/cplu.201900087
Abstrakt: Metal complexes of 3,7,13,17-tetrakis(di(4-carboxyphenyl)amino)-5,15-diazaporphyrin (MDAP-COOH; M=Pd, Cu) and their ethyl ester precursors (MDAP-COOEt; M=Pd, Cu) have been synthesized for use as near-infrared (NIR)-light-responsive photosensitizers. Under irradiation with visible or NIR light, PdDAP-COOEt in toluene generated singlet oxygen ( 1 O 2 ) with an excellent quantum yield (Φ Δ =0.99), whereas CuDAP-COOEt exhibited a lower efficiency (Φ Δ =0.21). The water-soluble Pd II complex PdDAP-COOH also behaved as a photosensitizer (Φ Δ =0.20) in a micellar solution. The photophysical properties of these dyes were measured by transient absorption techniques. It was found that the efficiency of the energy transfer from the triplet state of MDAP-COOR (R=Et, H) to the ground state of dioxygen was highly dependent on the peripheral substituents, the central metal, and the solvent. Furthermore, the phototoxicity of PdDAP-COOH toward HeLa cells under irradiation of NIR light (720 nm) was evaluated. As expected, PdDAP-COOH exhibited good photodynamic activity, and control experiments confirmed that 1 O 2 was generated as the active oxygen species.
(© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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