71410-72-5

Usage

Uses

5,15-Diphenyl-10,20-di(4-pyridyl)-21H,23H-porphine is a synthetic porphyrin.

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 109-97-7 pyrrole 
• 100-52-7 benzaldehyde 
• 56598-51-7 furfural 
• 52073-75-3 meso-(4-pyridyl)-2,2'-dipyrromethane 
• 107798-98-1 5-phenyldipyrromethane 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 

Downstream Products

• 1414350-57-4 [[5,15-bis(4-pyridyl)-10,20-diphenyl]porphinato]copper(II) 
• 1414350-58-5 [[5,15-bis(4-pyridyl)-10,20-diphenyl]porphinato]aluminum(III) methoxide 

Relevant academic research and scientific papers

Stimuli-Triggered reversible switching mechanism between H-and J-Type supramolecular assemblies of cationic porphyrins adsorbed on tungsten(VI) oxide surface

Supramolecular organic dye-inorganic semiconductor nanocrystal assemblies are potentially useful in a broad range of technologies and applications, including photovoltaic systems, but the molecular basis of the adsorption of dye molecules onto the semicon

Platinum(II) Metallatriangle: Construction, Coassembly with Polypeptide, and Application in Combined Cancer Photodynamic and Chemotherapy

The development of the supramolecular coordination complex with different shapes and dimensionalities lays the basis for its application in different areas. In this study, a porphyrin-based 3D organo-Pt(II) metallatriangle (MTA) was fabricated through the

Peripheral substituents of di(pyridiumyl)porphyrins affected on their interactions with DNA

meso- and β-Substituted di(pyridiumyl)porphyrins 3, 4, and 7 have been synthesized and their interactions with DNA have been investigated. meso-Substituted porphyrins showed the stronger effect on DNA than that of β-substituted porphyrin. Cytoxicity of co

Acid catalysis in confined channels of metal-organic frameworks: Boosting orthoformate hydrolysis in basic solutions

Enzymes use a confined docking cavity and residual groups in the cavity to regulate substrate selectivity and catalytic activity. By mimicking enzymes, we herein report that metal-organic framework (MOF) KLASCC-1, with channels and inside-channel pyridyl groups, can promote orthoformate hydrolysis in basic solutions. By studying pH-dependent hydrolysis and using an analogue MOF that lacks inside-channel pyridyl groups, we proved protonated pyridyl groups as acid catalytic sites for orthoformate hydrolysis. By using MOFs with only open pyridyl groups, we demonstrated the necessity of the confined channels. X-ray diffraction structures of KLASCC-1 with encapsulated substrates confirmed that these channels can regulate activity and size selectivity. Recycling tests and crystallographic studies confirmed that KLASCC-1 kept its framework structure in catalysis. This work shows the potentials of using MOFs for host-guest catalysis that cannot be otherwise completed and underlines the advantages of using crystal engineering to identify active sites.

2D amphiphilic organoplatinum(II) metallacycles: their syntheses, self-assembly in water and potential application in photodynamic therapy

Two 2D amphiphilic organoplatinum(ii) metallacycles with a porphyrin unit as the core and hydrophilic glycol units as the tail were designed and fabricated successfully through a new method called “coordination-driven self-assembly”. They can self-assembl

Photodynamic effect of meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins on HaCaT keratinocytes

Sixteen porphyrins, including neutral, anionic and cationic meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins were herein evaluated in terms of their photosensitizing properties against HaCaT keratinocytes. After an initial screening, the cationic porphyrins were studied in more details, by both determining their log POWand performing PDT assays in lower porphyrin concentrations. Porphyrins presenting two or more adjacent positively charged groups, directly linked to the macrocycle meso positions, appeared to be the most effective photosensitizers. The present study also included the dicationic 5,10-diphenyl-15,20-di(1-methylpyridinium-4-yl)porphyrin (14b), which has previously shown promising results on a psoriasis-like in vivo model. Overall results indicated that the beneficial effect related to porphyrins on psoriasis can be related to the decreasing of keratinocyte viability. Furthermore, some of the cationic porphyrins studied appeared as candidates to be utilized as photosensitizers for psoriasis treatment.

In vitro photodynamic inactivation of conidia of the phytopathogenic fungus Colletotrichum graminicola with cationic porphyrins

Photodynamic inactivation (PDI) is an efficient approach for the elimination of a series of microorganisms; however, PDI involving phytopathogenic filamentous fungi is scarce in the literature. In the present study, we have demonstrated the photoinactivating properties of five cationic meso-(1-methyl-4-pyridinio)porphyrins on conidia of the phytopathogen Colletotrichum graminicola. For this purpose, photophysical properties (photostability and 1O2 singlet production) of the porphyrins under study were first evaluated. PDI assays were then performed with a fluence of 30, 60, 90 and 120 J cm-2 and varying the porphyrin concentration from 1 to 25 μmol L-1. Considering the lowest concentration that enabled the best photoinactivation, with the respective lowest effective irradiation time, the meso-(1-methyl-4-pyridinio)porphyrins herein studied could be ranked as follows: triple-charged 4 (1 μmol L-1 with a fluence of 30 J cm-2) > double-charged-trans2 (1 μmol L-1 with 60 J cm-2) > tetra-charged 5 (15 μmol L-1 with 90 J cm-2) > mono-charged 1 (25 μmol L-1 with 120 J cm-2). Double-charged-cis-porphyrin 3 inactivated C. graminicola conidia in the absence of light. Evaluation of the porphyrin binding to the conidia and fluorescence microscopic analysis were also performed, which were in agreement with the PDI results. In conclusion, the cationic porphyrins herein studied were considered efficient photosensitizers to inactivate C. graminicola conidia. The amount and position of positive charges are related to the compounds' amphiphilicity and therefore to their photodynamic activity.

Hyperporphyrin effects in the spectroscopy of protonated porphyrins with 4-aminophenyl and 4-pyridyl meso substituents

Spectrophotometric titrations for a full series of 4-aminophenyl/4-pyridyl meso-substituted porphyrins were carried out using methanesulfonic acid in DMSO to study the hyperporphyrin effect across different substitution patterns. The series included zero, one, two (cis and trans), three, and four meso(4-aminophenyl) groups, with the remaining meso substituents being 4-pyridyl groups. The peripheral pyridyl groups consistently protonate before the interior porphyrin pyrrole nitrogens, which protonate before the aminophenyl groups. Aminophenyl substituents increase the basicity of the pyrrole nitrogens and lead to distinctive hyperporphyrin spectra with a broad Soret band and a strong red absorption. The structure proposed to give rise to these spectra is the previously proposed charge-transfer interaction between the aminophenyl and the protonated pyrrole. A novel hyperporphyrin structure involving charge-transfer interactions between two peripheral substituents is also proposed in one case, the triply protonated (+3) porphyrin with three aminophenyls and one pyridyl substituent; two of the aminophenyl groups delocalize the charges on the interior nitrogens, while the third aminophenyl group delocalizes with the protonated pyridyl.

New meso-substituted trans-A2B2 di(4-pyridyl) porphyrins as building blocks for metal-mediated self-assembling of 4 + 4 Re(i)-porphyrin metallacycles

The reaction between 5-(4-pyridyl)dipyrrylmethane and aromatic aldehydes affords meso-arylsubstituted trans-A2B2 di(4-pyridyl)porphyrins which are key building blocks in the metal-mediated self-assembling of supramolecular structures

Dicationic pyridium porphyrins appending different peripheral substituents: Synthesis and studies for their interactions with DNA

Twelve trans-dicationic pyridium porphyrins appending different peripheral substituents were synthesized and their abilities to bind and cleave DNA under irradiation have been investigated. Their binding modes to DNA were studied by UV-vis spectroscopy, circular dichroism. The apparent constants were measured by EB competitive fluorescence method and most of them were in the range of 104-105 M-1. We found that both the position of positive charges and steric hindrance could greatly influence their binding affinities and modes to DNA, and then affect their photocleaving abilities to DNA.