266341-16-6

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 874-60-2 4-methyl-benzoyl chloride 
• 147804-55-5 5-(4-methylphenyl)dipyrromethane 

Downstream Products

• 57412-11-0 5-(2-pyridyl)-10,15,20-tri-p-tolylporphyrin 
• 119770-80-8 5-(4-bromophenyl)-10,15,20-tri-p-tolyl-porphyrin 
• 57105-80-3 5,10,15-tris(4-methylphenyl)-20-(4-methoxycarbonylphenyl)porphyrin 

Relevant academic research and scientific papers

Singlet-singlet energy transfer in carbazole-porphyrin dyads and triads

Donor-π-Acceptor (D-π-A) type carbazole-porphyrin dyads and triads were synthesized in good yields through palladium catalyzed coupling reactions. The length of the spacer between the D (carbazole) and A (porphyrin) was varied from “phenylethyne” to “ethyne linkage”. The effect of the linker length on the spectral properties of these D-π-A dyads and triads was studied. The N-butyl-3-ethynyl-carbazole was coupled with different porphyrins bearing either one or two meso-p-iodophenyl group/meso-bromo groups using palladium catalyst. All the dyads and triads were characterized by MALDI-MS, NMR, UV–vis absorption, fluorescence and cyclic voltammetry techniques. The S1 emission dynamics were analyzed by time-resolved spectroscopy (TCSPC); an efficient energy transfer up to 84% was observed from donor groups to the porphyrin core. Electrochemical studies revealed that, compounds having freebase porphyrin components are difficult to reduce as indicated by the cathodic shift in their reduction potentials. On the contrary, the compounds having zinc porphyrin components are easy to reduce as reflected by the anodic shift in their reduction potentials. The lowest HOMO-LUMO gap was found for the dyad which has short linker between D and A.

Synthesis and photophysical characterization of porphyrin, chlorin and bacteriochlorin molecules bearing tethers for surface attachment

The ability to tailor synthetic porphyrin, chlorin and bacteriochlorin molecules holds promise for diverse studies in artificial photosynthesis. Toward this goal, the synthesis and photophysical characterization of five tetrapyrrole compounds is described

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.

Nearly chromatography-free synthesis of the A3B-porphyrin 5-(4-hydroxymethylphenyl)-10,15,20-tri-p-tolylporphinatozinc(II)

Rational routes to synthetic porphyrins bearing distinct meso-substituents have typically been implemented at modest scale (3B-porphyrin 5-(4-hydroxymethylphenyl)-10,15,20-tri-p- tolylporphinatozinc(II) (Zn-1) is required in multigram quantities for possible commercial use in information storage applications. The synthesis of Zn-1 has been carried out by reaction of 5-(4-hydroxymethylphenyl)dipyrromethane and the dicarbinol derived from 1,9-di-p-toluoyl-5-p-tolyldipyrromethane. Four improvements have been made to the steps leading to the dipyrromethane and dipyrromethane-dicarbinol: (i) use of 50 equiv of pyrrole in the condensation of an aldehyde to give the dipyrromethane (versus 100 equiv previously), (ii) 1,9-diacylation of a dipyrromethane using the hindered Grignard reagent 2,6-dimethylphenylmagnesium bromide and p-toluoyl chloride to give the 1,9-diacyl versus 1-acyl products in > 10:1 ratio (versus 4:1 using EtMgBr), (iii) isolation of the dibutyltin complex of the 1,9-diacyldipyrromethane from the crude reaction mixture by direct crystallization using methanol/methyl tert-butyl ether (MTBE) (versus silica chromatography), and (iv) reduction of the dibutyltin complex of the 1,9-diacyldipyrromethane (250 mM) with ～10-15 mol equiv of NaBH4 (versus 25 mM and 40 mol equiv). The procedures have been carried out with no chromatography at large scale, affording the dipyrromethane (31, 59, or 79 g), the dibutyltin complex of a 1,9-diacyldipyrromethane (361 g), and reduction of the latter (45 g). The porphyrin-forming reaction has been performed (25 mM reactants at 50-mmol scale, or 10 mM at 64-mmol scale) in a two-step process of condensation and oxidation to give the free base porphyrin 1 in 3.7- or 5.8-g quantities. Metalation with zinc acetate afforded Zn-1, which was isolated by direct crystallization. Taken together, the various improvements facilitate synthesis of the target porphyrin Zn-1 and may have broad applicability.

Synthesis of porphyrins bearing hydrocarbon tethers and facile covalent attachment to Si(100)

The use of redox-active molecules as the active storage elements in memory chips requires the ability to attach the molecules to an electroactive surface in a reliable and robust manner. To explore the use of porphyrins tethered to silicon via carbosilane

Corrole synthesis by dipyrromethane-dicarbinol and 2,2′-bipyrrole condensation

A3 and trans-A2B tris-aryl corroles 1a-c have been synthesized in up to 12% yield by BF3·Et2O-catalyzed condensation of dipyrromethane-dicarbinol and 2,2′-bipyrrole (1:1 ratio) in acetonitrile at room temperatur