14945-24-5Relevant articles and documents
Sequential Protonation of meso-(p-(Dimethylamino)phenyl)porphyrins: Charge-Transfer Excited States Producing Hyperporphyrins
Ojadi, Emmanuel C. A.,Linschitz, Henry,Gouterman, Martin,Walter, Robert I.,Lindsey, Jonathan S.,et al.
, p. 13192 - 13197 (1993)
Successive protonation by trifluoroacetic acid of meso-tetraphenylporphyrin derivatives bearing one, two or four p-dimethylamino groups gives rise to new types of spectra.With one free amino group, the spectrum of the centrally protonated porphyrin shows a strong far-red band, a broad, flat absorption in the visible, and a less intense Soret band.With two or more free amino groups, the Soret band of the centrally protonated porphyrin is further split into two components.Complete protonation, including the peripheral amino groups, in all cases restores the spectral structure of the unsubstituted tetraphenylporphyrin dication.The spectra of the dianions of tetraanilino- and tetraphenylporphyrins are also similar.These results, and the related behavior of p-oxyphenylporphyrins and protonated Schiff base porphyrins, lead to a general interpretation of hyperporphyrin spectra in terms of charge-transfer excited states, involving charge movement either into or out of the porphyrin ring.
Docking studies, antitumor and antioxidant evaluation of newly synthesized porphyrin and metalloporphyrin derivatives
Abou-Zeid, Laila,Ahmed, Asmaa,El-Asmy, Hala A.,Fadda, Ahmed A.,Omar, Walaa A. E.
, (2020/08/24)
In this work, we have synthesized a series of novel porphyrin derivatives, 1–5, in high yields. The metal complexes of two of the newly synthesized porphyrin derivatives, 1a–d and 2a–d, have also been synthesized in high yields and characterized. In the synthesis of the new porphyrins and metalloporphrins, we employed our reported strategy in which we utilized N,N-dimethylformamide (DMF) as a capping agent in the reaction of pyrrole with different hetero-aryl aldehydes. The new porphyrin derivatives are equipped with different aromatic substituents and hetero-cycles at the peripheral position. The structures of the new compounds were confirmed by elemental and spectral analyses. The geometry and magnetic properties of the new metalloporphyrins 1a–d and 2a–d have also been studied. Antioxidant and cytotoxic activities of the new compounds were evaluated and structure-activity relationships were performed. Porphyrin derivatives 2a and 4 showed exceptional antioxidant activity compared to ascorbic acid as a reference. While the derivatives 2, 3, and 5 exhibited very strong cytotoxic activity against two human cell lines, HePG-2 and MCF-7. Docking for the most promising antioxidant porphyrins, 2a and 4, into the binding active site of antioxidant protein Human Peroxiredoxin (code: 1HD2) has been carried out to detect the degree of recognition antioxidant activity. Molecular docking of the most cytotoxic active porphyrins, 3 and 5, into the biding site of telomerase inhibitor enzyme has been carried out to assess the degree of recognition cytotoxic activity.
Palladium(II) tetrakis(4-N,N,N-trimethylammoniumphenylene)porphyrin supported on ion-exchange resins as efficient and reusable catalysts for C-C coupling reactions
Sadegh, Faranak,Bagheri, Omid,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj
, p. 46 - 57 (2014/04/03)
In this research, the Heck and Suzuki reactions catalyzed by tetrakis(4-N,N,N-trimethylammoniumphenylene)porphyrinatopalladium(II) iodide, [Pd(TTMAPP)]I4, immobilized on ion-exchange resins such as Dowex 50 WX8 and Amberlite IR-120 are reported. In this manner, first, tetrakis(4-N,N-dimethylaminophenylene)porphyrin was converted to tetrakis(4-N,N,N-trimethylammoniumphenylene)porphyrin iodide, [H 2TTMAPP]I4, with methyl iodide. Then this water soluble porphyrin was metalated by palladium(II) chloride and the [Pd(TTMAPP)]I 4 was produced. This cationic palladium porphyrin was immobilized onto the ionic supports via electrostatic interactions. The catalysts, [Pd(TTMAPP)]@Dowex 50 WX8 and [Pd(TTMAPP)]@Amberlit IR-120, were characterized by FT-IR and diffuse reflectance UV-Vis spectroscopic methods, and scanning electron microscopy. These heterogeneous catalysts are thermally stable, oxygen insensitive, phosphine-free, air- and moisture-stable in the C-C coupling reactions and are reusable several times without significant loss of their catalytic activity.
