57412-12-1

Upstream product

• 109-97-7 pyrrole 
• 104-87-0 4-methyl-benzaldehyde 
• 122-85-0 para-acetamidobenzaldehyde 
• 147804-55-5 5-(4-methylphenyl)dipyrromethane 

Downstream Products

• 133308-60-8 4-methyl-2,2'-bipyridyl-N-(5-p-phenylene-10,15,20-tri-p-tolylporphyrin)-4'-amide 
• 73170-32-8 5-(4-aminophenyl)-10,15,20-tris-(4-methylphenyl)-porphyrin 

Relevant academic research and scientific papers

Photophysical studies of tetratolylporphyrin photosensitizers for potential medical applications

A group of meso-substituted synthetic tetratolylporphyrins was investigated by the methods of absorption and fluorescence spectroscopies as well as steady-state and time-resolved photothermal spectroscopies. The experiments were carried out in the air, oxygen or nitrogen atmospheres, at two temperatures. The details concerning the fast and slow deactivation processes of excitation energy of the dyes were studied. The estimated quantum yield of fluorescence and the efficiency of (S1-T1) intersystem crossing process give a possibility to evaluate the population yield and quenching rate of the triplet state, important for the therapeutic application, mostly mediated by the T1-state. For tetrapyrrole with the carboxyphenyl group substituted in meso-position, the triplet state yield was the highest, of 0.86-0.94, whereas the porphyrin with aminophenyl group seemed to be efficient singlet oxygen generators (0.81-0.99) with a high rate constant of its excited triplet state quenching by molecular oxygen.

The spectroscopic characterisation of proline derivatives of tolyl-porphyrins and their iron and cobalt complexes

The new tolylporphyrin-prolin derivatives: TTP-CONH-Pro-COOCH2C6H5 and TTP-NHCO-Pro-Cbz and their iron and cobalt complexes have been synthesised and characterised by MS, IR, UV-vis, EPR and LIOAS spectroscopy studies. The EPR investigations demonstrate that Fe(III) and Co(II) ions are located in the site of distorted axial symmetry. Besides, for ferric porphyrins a thermally induced spin crossover was observed. The possibility of the applications in photodynamic therapy or diagnostics of cancerous tissues of the porphyrins obtained was studied. In the light of the experiments performed, from the group of investigated compounds, it seems that the metal-free TTP-NHCO-Pro-Cbz is well suited for PDT.

Photosensitization of thin SnO2 nanocrystalline semiconductor film electrodes with metallodiporphyrin

Sensitized photocurrent generation is observed with a porphyrin dyad (PZn-P) and its structural moieties: 5-(4-carboxyphenyl)-10,15,20-tris(4-methylphenyl) porphyrin (P) and Zn(II) 5-(4-carboxyphenyl)-10,15,20-tris(4-methylphenyl) porphyrin (PZn). The dyes were adsorbed to saturation on a nanocrystalline SnO2 thin film, employed as working electrode in a photoelectrochemical cell. The metallized and unmetallized moieties possess different singlet state energies and redox properties. In both, solution and adsorbed state, nearly complete singlet-singlet energy transfer from the PZn to P has been determined in the dyad. PZn is less efficient than P in the photocurrent generation, but is a suitable energy donor in the dyad molecule. The generation of photoelectrical effects by the dyad is less effective in comparison with P. Considering the oxidation potentials of the two moieties in PZn-P, a mechanism is proposed where the oxidized metallized porphyrin enhances the back electron-transfer process.

Porphyrin–schiff base conjugates bearing basic amino groups as antimicrobial phototherapeutic agents

New porphyrin–Schiff base conjugates bearing one (6) and two (7) basic amino groups were synthesized by condensation between tetrapyrrolic macrocycle-containing amine functions and 4-(3-(N,N-dimethylamino)propoxy)benzaldehyde. This approach allowed us to easily obtain porphyrins substituted by positive charge precursor groups in aqueous media. These compounds showed the typical Soret and four Q absorption bands with red fluorescence emission (ΦF ~ 0.12) in N,N-dimethylformamide. Porphyrins 6 and 7 photosensitized the generation of O2 (1?g) (Φ? ~ 0.44) and the photo-oxidation of L-tryptophan. The decomposition of this amino acid was mainly mediated by a type II photoprocess. Moreover, the addition of KI strongly quenched the photodynamic action through a reaction with O2 (1?g) to produce iodine. The photodynamic inactivation capacity induced by porphyrins 6 and 7 was evaluated in Staphylococcus aureus, Escherichia coli, and Candida albicans. Furthermore, the photoinactivation of these microorganisms was improved using potentiation with iodide anions. These porphyrins containing basic aliphatic amino groups can be protonated in biological systems, which provides an amphiphilic character to the tetrapyrrolic macrocycle. This effect allows one to increase the interaction with the cell wall, thus improving photocytotoxic activity against microorganisms.

Synthesis of porphyrin dyads with potential use in solar energy conversion

A convenient procedure for the synthesis of porphyrin derivative dyads is described. The dyads consist of a free base porphyrin covalently linked to a zinc porphyrin or ferrocene by an amide bond. 5-(4-Substituted phenyl)- 10,15,20-tris(4-methylphenyl) po

Synthesis of 5-(4-acetamidophenyl)-10,15,20-tris(4-substituted phenyl) porphyrins using dipyrromethanes

A convenient procedure for the synthesis of 5-(4-acetamidophenyl)- 10,15,20-tris(4-substituted phenyl) porphyrins (5-8) from dipyrromethane is reported, meso-(4-Substituted phenyl) dipyrromethanes (1-4) were obtained in yields of 72-84% by the reaction of 4-substituted benzaldehyde with an excess of pyrrole. The porphyrins (5-8) were isolated with appreciable yields of 15- 17%.

Synthesis and Spectroscopic Investigation of Directly Azobenzene Bridged Diporphyrins

The synthesis of new directly azobenzene bridged diporphyrins is described.The spectroscopic properties of the new compounds are discussed.