214554-44-6

Upstream product

• 109-97-7 pyrrole 
• 619-66-9 4-Carboxybenzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 873955-90-9 4-[bis-(1H-pyrrol-2-yl)-methyl]-N-isopropyl-benzamide 
• 61449-63-6 5-(4-carboxyphenyl)-10,15,20-tris(4-methylphenyl) porphyrin 

Relevant academic research and scientific papers

Carbazole Substituted BODIPYs: Synthesis, Computational, Electrochemical and DSSC Studies

Carbazole and p-anisyl substituted BODIPY dyes with a cyanoacetic acid anchoring group have been prepared and their spectral, electrochemical properties and photosensitizing potential in DSSC have been evaluated. X-ray structure of N-phenylcarbazole subst

Synthesis and optical properties of BODIPY with active group on meso-position

Background: In this work a few approaches for the synthesis of 4,4-difluoro-8-(4′-carboxyphenyl)-4-bora-3a,4a-diaza-s-indacene are considered. The process of obtaining this boron fluoride complex involves the following stages: introduction of the protective group (methoxy-, 1′-pyrrolidine-2,5-dion-, trichloroethoxy-) on the carboxy-group of 4-formylbenzoic acid, condensation with pyrrole, removal of protection, oxidation, and complexation proper. A method of direct condensation of pyrrole with the 4-formylbenzoic acid in the presence of a catalytic amount of 0.1 M HCl was proposed to achieve a high yield of the target product. All synthesized compounds were characterized by infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectrometry and elemental analysis. Values of fluorescence quantum yield and Stokes shift were calculated for boron fluoride complexes of dipyrrolylmethenes. Methods: IR spectra were recorded on a Bruker Vertex 80V device in the regions of 7500-350 cm-1 from pellets with KBr. The NMR spectral studies on the nuclei 1H and 13C were performed on a Bruker Avance-500 instrument (500.13 MHz) in CDCl3, the internal standard was TMS. Elemental analyses of crystalline compounds were carried out on a FlashEA 1112 analyzer. Mass spectra were registered on a JMS-700 JEOL (FAB) and JMS-100GCV JEOL (EI) mass-spectrometers. UV/V is spectra and fluorescence spectra were recorded on a spectrofluorimeter CM 2203 (SOLAR) in CH2Cl2, with square quartz cavity being 10 mm thick. The fluorescence quantum yield was determined by formula utilizing fluorescein in 0.1 M NaOH as a standard (ΦS=0.85). Results: All the synthesized compounds have a smaller fluorescence quantum yield as compared to the standard and most BODIPY, in which the meso-position does not contain aryl and the other mobile substituents. The decrease in the quantum yield of meso-aryl-substituted BODIPY due to the rotation of the meso-substituent relative BODIPY core leads to non-radiative transitions. Fluorophores are stable upon illumination (no changes in the electronic absorption and fluorescence spectra are observed when they are affected by a continuous light). The Stokes shift is from 30 to 52 nm. Conclusion: A few approaches to synthesize 4,4-difluoro-8-(4′-carboxyphenyl)-4-bora-3a,4a-diaza-s-indacene are considered. The process of obtaining this boron fluoride complex involves the following stages: introduction of the protective group (methoxy-, 1′-pyrrolidine-2,5-dion-, trichloroethoxy-) on the carboxy-group of 4-formylbenzoic acid, condensation with pyrrole, removal of protection, oxidation, and complexation proper. A method of direct condensation of pyrrole with the 4-formylbenzoic acid in the presence of a catalytic amount of 0.1 M HCl was proposed to achieve a high yield of the target product. Values of fluorescence quantum yield and Stokes shift were calculated for boron fluoride complexes of dipyrrolylmethenes.

Novel polycarboxylate porphyrins: Synthesis, characterization, photophysical properties and preliminary antimicrobial study against Gram-positive bacteria

We describe the synthesis, characterization and photophysical properties of two new polycarboxylic photosensitizers. Owing to their structural design, these two compounds show water solubilities larger than natural carboxylic photosensitizers (e.g., proto

Study of kinetics of silver with tetra(p-carboxyphenyl)porphyrin

The kinetics formation of labile complex Ag(I) tetra(p-carboxyphenyl) porphyrin (TCPP) was investigated at 25 °C and I = 0.1 M (NaNO3). By spectrophotometric titration, the composition ratio of the complex was established to be 2:1 (Ag:H2TCPP). The equilibrium constant (K) was found to be log 10-6.53. Binding of the first Ag(I) was found to be rate determining step with rate constant, k1 = 4.67 × 102. A plausible mechanism is discussed.

Compositions and methods for treating cancer

The invention features compositions and methods for treating or alleviating a symptom of cancer. The compositions and methods of the invention direct supra-lethal doses of radiation, called Hot-Spots, to virtually all cancer cell types.

A new hydrogen-bonding motif with constituents bearing donor and acceptor sites 7 ? apart

Aryl substituted dipyrromethanes [di(pyrrol-2-yl)-phenyl-methanes] with hydrogen acceptor substituents R in para position of the aryl ring [R = CO 2Me, CO2H, CONH(iPr) and NH2] located 7 ? apart from the hydrogen donor pyr

Rational Syntheses of Porphyrins Bearing up to Four Different Meso Substituents

Porphyrins bearing specific patterns of substituents are crucial building blocks in biomimetic and materials chemistry. We have developed methodology that avoids statistical reactions, employs minimal chromatography, and affords up to gram quantities of regioisomerically pure porphyrins bearing predesignated patterns of up to four different meso substituents. The methodology is based upon the availability of multigram quantities of dipyrromethanes. A procedure for the diacylation of dipyrromethanes using EtMgBr and an acid chloride has been refined. A new procedure for the preparation of unsymmetrical diacyl dipyrromethanes has been developed that involves (1) monoacylation with EtMgBr and a pyridyl benzothioate followed by (2) introduction of the second acyl unit upon reaction with EtMgBr and an acid chloride. The scope of these acylation methods has been examined by preparing multigram quantities of diacyl dipyrromethanes bearing a variety of substituents. Reduction of the diacyl dipyrromethane to the corresponding dipyrromethane-dicarbinol is achieved with NaBH4 in methanolic THF. Porphyrin formation involves the acid-catalyzed condensation of a dipyrromethane-dicarbinol and a dipyrromethane followed by oxidation with DDQ. Optimal conditions for the condensation were identified after examining various reaction parameters (solvent, temperature, acid, concentration, time). The conditions identified (2.5 mM reactants in acetonitrile containing 30 mM TFA at room temperature for 3B, trans-A2B2, trans-AB2C, cis-A2B2, cis-A2BC, and ABCD were prepared, including >1-g quantities of three porphyrins.