71159-98-3Relevant articles and documents
Cationic pyrrolidine/pyrroline-substituted porphyrins as efficient photosensitizers against e. Coli
Almeida, Adelaide,Dias, Cristina J.,Faustino, M. Amparo F.,Gomes, Ana T. P. C.,Ladeira, Bruno M. F.,Moura, Nuno M. M.,Neves, Maria G. P. M. S.,Tomé, Augusto C.
, (2021)
New porphyrin–pyrrolidine/pyrroline conjugates were prepared by revisiting 1,3-dipolar cycloaddition reactions between a porphyrinic azomethine ylide and a series of dipolarophiles. Cationic conjugates obtained by alkylation of the pyrrolidine/pyrroline cycloadducts showed ability to generate singlet oxygen and to produce iodine in presence of KI when irradiated with visible light. Some of the cationic derivatives showed photobactericidal properties towards a Gram-negative bioluminescent E. coli. In all cases, these features were significantly improved using KI as coadjutant, allowing, under the tested conditions, the photoinactivation of the bacterium until the detection limit of the method with a drastic reduction of the required photosensitizer concentration and irradiation time. The obtained results showed a high correlation between the ability of the cationic porphyrin derivative to produce singlet oxygen and iodine and its E. coli photoinactivation profile.
A new synthetic approach to benzoporphyrins and Kroehnke type porphyrin-2-ylpyridines
Moura, Nuno M. M.,Faustino, Maria A. F.,Neves, Maria G. P. M. S.,Paz, Filipe A. Almeida,Silva, Artur M. S.,Tome, Augusto C.,Cavaleiro, Jose A. S.
, p. 6142 - 6144 (2012)
The reaction of 2-formyl-5,10,15,20-tetraphenylporphyrin with aryl methyl ketones and ammonium acetate, in the presence of La(OTf)3, affords benzoporphyrins and 2-(2,6-diarylpyridin-4-yl)porphyrins. This methodology was used to prepare, for the
Synthesis, spectral and redox properties of closely spaced pyrrole-β-position-linked porphyrin-fullerene dyads
Wu, Zhen-Yi,Yang, Sheng-Yan
, p. 244 - 254 (2019/04/17)
Two free base meso-tetraphenylporphyrin-fullerene dyads, H2PMe-C60, H2POMe-C60, and their zinc complexes, ZnPMe-C60 and ZnPOMe-C60, which the para positions of the meso-tetrasubstituted phenyl groups of the porphyrin core were substituted by methyl(-Me) and methoxyl(-OMe) groups respectively, were synthesized. The porphyrin unit in the synthesized dyads is directly linked to the fullerene entity through the pyrrole-β- position rather than through the traditionally meso-substituted phenyl group, which may be more favorable for electron communication between the donor and the acceptor. They are fully characterized by mass spectrometry, nuclear magnetic resonance, infrared spectroscopy and ultraviolet visible spectroscopy. Experimental results obtained from steady-state fluorescence spectroscopy and cyclic voltammetry show that the coordination of the zinc ions lead to an increase in the singlet excited state energy of the metallated porphyrin unit by about 0.15 eV, and to a reduce in the HOMO level and in the HOMO-LUMO energy gap. The molecular reorganization energy decreases after the electron-donating groups of -Me or -OMe attaching to the para position of the meso-phenyl group of the porphyrin moiety. The results of the energy calculations show that photoinduced electron transfer is thermodynamically favorable for the synthesized porphyrin-C60 dyads. There exists a competition between the photoinduced electron transfer and energy transfer processes from the first singlet excited state of porphyrin core to fullerene moiety. The photoinduced electron transfer rate constant of the dyads were calculated according to Marcus theory. The results indicate that the coordination of metal zinc ions lead to great increase in the electron transfer rate constant. Further, the photoinduced electron transfer rate constant increases in the order ZnP-C60, ZnPMe-C60, ZnPOMe-C60.
