73170-32-8

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 143859-77-2 2,2'-[(4-nitrophenyl)methylene]bis(1H-pyrrole) 
• 147804-55-5 5-(4-methylphenyl)dipyrromethane 
• 555-16-8 4-nitrobenzaldehdye 
• 57412-12-1 5-(4-Acetamidophenyl)-10,15,20-tris(4-methylphenyl) porphyrin 
• 94815-62-0 5,10,15-tris(p-methylphenyl)-20-(p-nitrophenyl)porphyrin 

Downstream Products

• 133308-59-5 N,N'-di(5-p-phenylene-tri-p-tolylporphyrin)-2,2'-bipyridyl-4,4'-diamide 
• 110390-86-8 4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyl-18-(2,6,6-trimethyl-cyclohex-1-enyl)-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-N-[4-((1Z,4Z,9Z,15Z)-10,15,20-tri-p-tolyl-porphyrin-5-yl)-phenyl]-benzamide 
• 133308-58-4 N,N'-di(5-p-phenylene-10,15,20-tri-p-tolylporphyrin)-1,10-phenanthroline-4,4'-diamide 
• 133308-60-8 4-methyl-2,2'-bipyridyl-N-(5-p-phenylene-10,15,20-tri-p-tolylporphyrin)-4'-amide 

Relevant academic research and scientific papers

Meso-Schiff-base substituted porphyrin dimer dyes for dye-sensitized solar cells: Synthesis, electrochemical, and photovoltaic properties

Two novel large conjugated system meso-Schiff-base substituted porphyrin dimers, which contained the thienyl or p-methylphenyl functional groups, have been designed and synthesized for the efficient green dyes for dye-sensitized solar cells (DSSCs) applic

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.

Triaryl-substituted pyrrolo-p-phenylene-linked porphyrin-fullerene dyads: Expanding the structural diversity of photoactive materials

A protocol for the synthesis of pyrrolo-p-phenylene-linked porphyrin-fullerene dyads suitable as photoactive materials was developed. The sequence of aziridination – aziridine ring opening – 1,3-dipolar cycloaddition reactions enabled us to provide structural variability both to the porphyrin core and to pyrrole linker, which facilitates designing the electronic structure and morphological parameters of the dyads. The key porphyrin building blocks, nitro-porphyrins, were synthesized by a stochastic cyclocondensation of arenecarbaldehydes with p-nitrophenyl(dipyrrolyl)methane.

In silico study, synthesis, and cytotoxic activities of porphyrin derivatives

Five known porphyrins, 5,10,15,20-tetrakis(p-tolyl)porphyrin (TTP), 5,10,15,20-tetrakis(pbromophenyl) porphyrin (TBrPP), 5,10,15,20-tetrakis(p-aminophenyl)porphyrin (TAPP), 5,10,15- tris(tolyl)-20-mono(p-nitrophenyl)porphyrin (TrTMNP), 5,10,15-tris(tolyl)-20-mono(paminophenyl) porphyrin (TrTMAP), and three novel porphyrin derivatives, 5,15-di-[bis(3,4- ethylcarboxymethylenoxy)phenyl]-10,20-di(p-tolyl)porphyrin (DBECPDTP), 5,10-di-[bis(3,4- ethylcarboxymethylenoxy)phenyl]-15,20-di-(methylpyrazole-4-yl)porphyrin (cDBECPDPzP), 5,15-di- [bis(3,4-ethylcarboxymethylenoxy)phenyl]-10,20-di-(methylpyrazole-4-yl)porphyrin (DBECPDPzP), were used to study their interaction with protein targets (in silico study), and were synthesized. Their cytotoxic activities against cancer cell lines were tested using 3-(4,5-dimetiltiazol-2-il)-2,5- difeniltetrazolium bromide (MTT) assay. The interaction of porphyrin derivatives with carbonic anhydrase IX (CAIX) and REV-ERBβ proteins were studied by molecular docking and molecular dynamic simulation. In silico study results reveal that DBECPDPzP and TrTMNP showed the highest binding interaction with REV- ERBβ and CAIX, respectively, and both complexes of DBECPDPzPREV- ERBβ and TrTMNP-CAIX showed good and comparable stability during molecular dynamic simulation. The studied porphyrins have selective growth inhibition activities against tested cancer cells and are categorized as marginally active compounds based on their IC50.

Preparation and optical properties of polyimide films linked with porphyrinato Pd (II) and Pt (II) complexes through a triazine ring and application toward oxygen sensors

5-(3-Aminophenyl)-10,15,20-tri(4-methylphenyl) porphyrinato Pd (II) and Pt (II) complexes (2a-Pd) and (2a-Pt), respectively, were prepared from 5-(3-nitrophenyl)-10,15,20-tri(4-methyl-phenyl)porphyrin via two-step reactions, and reacted with cyanuric chloride to produce corresponding porphyrin derivatives (3a-Pd) and (3a-Pt) with a dichlorotriazine ring. Aromatic polyimides were prepared using diamine (4); triazine dichlorides having porphyrin units (3a-Pd), (3a-Pt), (3c-Pd), and (3c-Pt); fluoro-functionality 6-(p-perfluorononenyl oxyanilino)triazine-2,4-dichloride (6); and tetracarboxylic dianhydride (5) in N-methyl-2-pyrrolidone (NMP) at an elevated temperature up to 300 °C. The resulting viscous polymeric solution was cast on a glass plate, affording well-proportioned reddish transparent films with number-average molecular weights of 25,000–38,000. Glass transition temperatures of the polymers were ～230 °C; the films were stable up to 400 °C in air. The film emission spectra showed a broad peak ～670 nm, similar to those of porphyrins (2a-Pd) and (2a-Pt) dispersed in a polystyrene matrix. While the luminescence of these polymer films was quenched with oxygen, it rapidly recovered under a deoxygenated atmosphere. The polyimide film sensitivity to oxygen was higher under low oxygen concentrations than those of porphyrins (2a-Pd) and (2a-Pt) dispersed in polystyrene.

Synthesis of triazole-bridged unsymmetrical porphyrin dyads and porphyrin-ferrocene conjugates

A simple method has been used to synthesize four porphyrin azides with cores such as N4, N3S, N2SO and N 2S2 in 6090% yields by treating the corresponding aminoporphyrms with tert-butyl nitrite (tBuON

Chiral assembly of a pair of free base porphyrins and peroxidase-like activity of iron(III) porphyrins in four-α-helix bundle structures with dimerized two-α-helix polypeptides

A 5-(4α-bromoacetamidophenyl)-10,15,20-tritolylporphyrin was incorporated into a single-chain two-α-helix polypeptide containing 29 amino acid residues via the thiol side chain of a Cys residue. Two molecules of two-α-helix polypeptide connecting free base porphyrin (H2-porphyrin) were strongly associated to form a four-α-helix bundle structure by hydrophobic interaction among α-helix segments and porphyrin rings in aqueous solution. The dimer formation was demonstrated by gel filtration chromatography and various spectroscopic measurements. The Soret band in the UV/vis spectrum was broadened and red-shifted in aqueous solution. In the fluorescence spectrum with excitation at the Soret band the emission at 650 nm was quenched to 40% of the intensity measured in methanol. Especially, at the Soret band was observed a strongly split circular dichroism (CD) signal, which demonstrated the chiral assembly of a pair of porphyrins in a left-handed sense. With increasing methanol content, the intensity of this split signal was decreased and finally diminished probably due to dissociation of the porphyrin moieties in the peptides. The dimerized Fe(III)-porphyrin-linked two-α-helix polypeptide was examined for biomimetic peroxidase-like activity with H2O2 or 3-chloroperbenzoic acid (MCPBA) as the oxidant. The kcat/KM value for the oxidation of 3,7-dimethylamino-10-methylcarbamoylphenothiazine by the polypeptide with MCPBA was increased by 5000 times compared to that with H2O2. This fact suggests that Fe(III) porphyrin was located in the hydrophobic core and more easily accommodated an organic oxidant than does H2O2. The interior of the four-α-helix bundle structure may be further designed to mimic various haemproteins.

Synthesis, Spectroscopy, and Photocytotoxicity of Glycosylated Amino Acid Porphyrin Derivatives as Promising Molecules for Cancer Phototherapy

To obtain molecules that can target malignant cells, two series of new meso glucosylporphyrins bearing amino acid residues are synthesized in four steps. The first series contained n meso glycosyl moieties and (4 -n) alanyl groups on the ortho or para positions of the meso phenyl. In the second series, the carbohydrate moiety is separated from the aryl substituent by a serine unit. Starting from p- or o-nitrobenzaldehyde, p- or o-acetylbenzaldehyde or -tolualdehyde, and pyrrole, the glycosylnitrophenylporphyrins 3-6 and tritolylporphyrins 8a,b are synthesized under optimized conditions tailored from Lindsey's method. The nitro function is then reduced and N-Fmoc-L-alanine or acetylglycosylated N-Fmoc-serine are coupled on the amino function. A detailed 1H and 13C NMR study allows complete structural elucidation. The UV-visible fluorescence and MALDI mass spectra are presented. Compounds 19-22 produced 1O2, and photocytotoxicities against the K562 leukemia cell line are compared to hematoporphyrin. As a result of their sensitizing abilities, these resultant compounds are of considerable interest for photodynamic therapy.

Diporphyrinyl Derivatives of 1,10-Phenanthroline and 2,2'-Bipyridyl

The title derivatives were synthesized containing two meso-tri-p-tolylphenyleneporphyrin units attached via amide bridges to 4,7- and 4,4' positions of the respective heteroatomatic spacers.