266341-19-9

Upstream product

• 266341-16-6 1,9-bis(4-methylbenzoyl)-5-(4-methylphenyl)dipyrromethane 
• 874-60-2 4-methyl-benzoyl chloride 
• 147804-55-5 5-(4-methylphenyl)dipyrromethane 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 57412-11-0 5-(2-pyridyl)-10,15,20-tri-p-tolylporphyrin 
• 82498-08-6 Zn(II)-5-(4-methoxycarbonylphenyl)-10,15,20-tri-ptolylporphyrin 
• 121869-50-9 5-(4-hydroxymethylphenyl)-10,15,20-tris(4-methylphenyl)porphyrin 
• 61449-63-6 5-(4-carboxyphenyl)-10,15,20-tris(4-methylphenyl) porphyrin 

Relevant academic research and scientific papers

Porphyrin architectures tailored for studies of molecular information storage

A molecular approach to information storage employs redox-active molecules tethered to an electroactive surface. Zinc porphyrins tethered to Au(111) or Si(100) provide a benchmark for studies of information storage. Three sets of porphyrins have been synt

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.

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.

Synthesis of porphyrins designed for attachment to electroactive surfaces via one or more carbon tethers

Porphyrin compounds having a surface attachment group coupled thereto at the 5 position are described. The surface attachment group has the formula: wherein R is —CHCH2 or —CCH and Ar is an aromatic group. Methods and intermediates useful for m

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

Porphyrins Bearing Mono or Tripodal Benzylphosphonic Acid Tethers for Attachment to Oxide Surfaces

The ability to attach redox-active molecules to oxide surfaces in controlled architectures (distance, orientation, packing density) is essential for the design of a variety of molecular-based information storage devices. We describe the synthesis of a series of redox-active molecules wherein each molecule bears a benzylphosphonic acid tether. The redox-active molecules include zinc porphyrins, a cobalt porphyrin, and a ferrocene-zinc porphyrin. An analogous tripodal tether has been prepared that is based on a tris [4-(dihydroxyphosphorylmethyl)phenyl]-derivatized methane. A zinc porphyrin is linked to the methane vertex by a 1,4-phenylene unit. The tripodal systems are designed to improve monolayer stability and ensure vertical orientation of the redox-active porphyrin on the electroactive surface. For comparison purposes, a zinc porphyrin bearing a hexylphosphonic acid tether also has been prepared. The synthetic approaches for introduction of the phosphonic acid group include derivatization of a bromoalkyl porphyrin or use of a dimethyl or diethyl phosphonate substituted precursor in a porphyrin-forming reaction. The latter approach makes use of dipyrromethane building blocks bearing mono or tripodal dialkyl phosphonate groups. The zinc porphyrintripodal compound bearing benzylphosphonic acid legs tethered to a SiO2 surface (grown on doped Si) was electrically well-behaved and exhibited characteristic porphyrin oxidation/reduction waves. Collectively, a variety of porphyrinic molecules can now be prepared with tethers of different length, composition, and structure (mono or tripodal) for studies of molecular-based information storage on oxide surfaces.

Synthesis of phenylethyne-linked porphyrin dyads

Four new porphyrin dyads have been prepared for studies in artificial photosynthesis. The two porphyrins are joined at the meso positions via a phenylethyne linker and are present in zinc/zinc or zinc/free base metalation states. The porphyrin bearing the

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

Design, synthesis, and characterization of prototypical multistate counters in three distinct architectures

The storage of multiple bits of information in distinct molecular oxidation states is anticipated to afford extraordinarily high memory densities. Among redox-active molecules, lanthanide porphyrinic triple-decker complexes are attractive candidates for s