In view of their promising photosensitizing features, expanded porphyrins are gaining wide attention for their potential use both in photodynamic therapy of cancer and as likely photoactivated agent for water disinfection. Herein, we report a joint experimental and theoretical investigation on the 20-(4′-carboxyphenyl)-2,13-dimethyl- 3,12-diethyl-[22] pentaphyrin complex 4. The synthesis, NMR, UV–Vis and mass characterization of the new compound together with a detailed theoretical investigation of the photophysical properties, are presented. In particular, type I and type II photoreactions have been explored by means of DFT and its TDDFT formulation characterizing the electronic absorption spectra, providing singlet–triplet energy gap, vertical ionization potential and electron affinity. Results show that title compound is able to generate thecytotoxic singlet oxygen species supporting the application of the proposed molecule as a photoactivated agent for water disinfection.
Alberto, M., Comuzzi, C., Thandu, M., Adamo, C., Russo, N. (2016). 22π‑Electrons [1.1.1.1.1] pentaphyrin as a new photosensitizing agent for water disinfection: Experimental and theoretical characterization. THEORETICAL CHEMISTRY ACCOUNTS, 135(2) [10.1007/s00214-015-1794-4].
22π‑Electrons [1.1.1.1.1] pentaphyrin as a new photosensitizing agent for water disinfection: Experimental and theoretical characterization
Alberto M. E.;
2016
Abstract
In view of their promising photosensitizing features, expanded porphyrins are gaining wide attention for their potential use both in photodynamic therapy of cancer and as likely photoactivated agent for water disinfection. Herein, we report a joint experimental and theoretical investigation on the 20-(4′-carboxyphenyl)-2,13-dimethyl- 3,12-diethyl-[22] pentaphyrin complex 4. The synthesis, NMR, UV–Vis and mass characterization of the new compound together with a detailed theoretical investigation of the photophysical properties, are presented. In particular, type I and type II photoreactions have been explored by means of DFT and its TDDFT formulation characterizing the electronic absorption spectra, providing singlet–triplet energy gap, vertical ionization potential and electron affinity. Results show that title compound is able to generate thecytotoxic singlet oxygen species supporting the application of the proposed molecule as a photoactivated agent for water disinfection.
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