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Upstream product

• 71763-49-0 copper(II) 2-formyl-5,10,15,20-tetraphenylporphyrin 
• 14172-91-9 5,10,15,20-tetraphenylporphyrin Cu(II) complex 
• 68-12-2 N,N-dimethyl-formamide 
• 110350-65-7 2-formyl-5,10,15,20-tetraphenylporphyrinato zinc(II) 
• 872-73-1 N-methyl-2-methylpyridinium iodide 
• 14172-91-9 (tetraphenylporphyrin)copper(II) 
• 71763-49-0 β-formyl-5,10,15,20-tetrakis(phenyl)porphyrin copper(II) 

Relevant academic research and scientific papers

Cationic pyrrolidine/pyrroline-substituted porphyrins as efficient photosensitizers against e. Coli

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.

Synthesis, characterization and biological evaluation of cationic porphyrin-terpyridine derivatives

A simple access to a new series of cationic porphyrin-terpyridine derivatives is described. The key step to obtain the required neutral precursors as major products involved a Kr?hnke type approach. The methodology allowed also the isolation of the respective benzoporphyrins and porphyrin-chalcone type derivatives, and in one case a new 2-(2,4-terpyridin-6-yl)-porphyrin. The quaternization of the pyridyl groups was performed in the presence of the adequate alkyl iodide affording the dicationic derivatives in excellent yields. All the new conjugates were fully characterised and it was found that the cationic isomers can be efficiently differentiated by ESI-MS, as their behaviour can be intensively studied by mass spectrometry. The new methylated cationic porphyrin-terpyridine derivatives demonstrate an ability to generate singlet oxygen and their efficacy to photoinactivate bioluminescent Gram-negative E. coli was evaluated. A reduction in the bioluminescence signal, up to 5.4 log, was obtained with the most efficient photosensitiser.

A new synthetic approach to benzoporphyrins and Kroehnke type porphyrin-2-ylpyridines

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

A new 3,5-bisporphyrinylpyridine derivative as a fluorescent ratiometric probe for zinc ions

A new 3,5-disubstituted pyridine with two porphyrin moieties was prepared through an efficient synthetic approach involving 2-formyl-5,10,15,20- tetraphenylporphyrin (1), piperidine, and catalytic amounts of [La(OTf) 3]. 3,5-Bis(5,10,15,20-tetr

Synthesis, spectral and redox properties of closely spaced pyrrole-β-position-linked porphyrin-fullerene dyads

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.

Cationic β-vinyl substituted meso-tetraphenylporphyrins:

Several cationic beta-vinyl-pyridinium and beta-vinyl-quinolinium-meso- tetraphenylporphyrin derivatives were synthesized starting from 2-formyl-meso-tetraphenylporphyrin, and the corresponding Zn(II) complex, and different N-alkyl derivatives of 2- and 4-methylpyridine and 2- and 4-methylquinoline. The new compounds were obtained in a one-step process via base catalyzed aldol-type condensation reactions. Electrospray ionization mass spectrometry (ESI-MS) and ultraviolet-visible (UV-vis) spectroscopy were used to investigate the binding mode of the synthesized cationic beta-vinyl-pyridinium and beta-vinyl-quinolinium-meso-tetraphenylporphyrin derivatives with a short GC duplex oligonucleotide. Analysis of the obtained mass spectrometry results indicates the probable occurrence of outside binding. UV-vis spectroscopy data also points to non-intercalation. The potential photosensitizing capacity of these compounds was also ascertained from preliminary photophysical studies.

Reductive Amination-A convenient method for generating diverse, mono-functionalised 5,10,15,20-tetraphenyl porphyrins

Formylation followed by reductive amination of 5,10,15,20-tetraphenyl porphyrin (TPP) is shown to be a versatile synthetic procedure for monosubstitution of the porphyrin core re-giospecifically at one β-position. A diverse range of substituents can be introduced in this way in good yields, including cyclen aza-crown macrocycles. Georg Thieme Verlag Stuttgart.

PORPHYRINS AND THEIR DERIVATIVES. XVI. SYNTHESIS OF α,β-UNSATURATED TETRAPHENYLPORPHYRIN ALDEHYDES AND THEIR PROPERTIES

The Wittig condensation of 2-formyl-meso-tetraphenylporphyrin and its copper complex with 1,3-dioxolan-2-ylmethyltriphenylphosphonium bromide in benzene in the presence of crown ether leads to 2-(2-formylvinyl) derivatives.The latter react with the phosph