307930-64-9Relevant academic research and scientific papers
Enantiotopos-selective C-H oxygenation catalyzed by a supramolecular ruthenium complex
Frost, James R.,Huber, Stefan M.,Breitenlechner, Stefan,Bannwarth, Christoph,Bach, Thorsten
, p. 691 - 695 (2015/03/04)
Spirocyclic oxindoles undergo an enantioselective oxygenation reaction (nine examples; e.r. up to 97:3) upon catalysis by a chiral ruthenium porphyrin complex (1 mol%). The catalyst exhibits a lactam ring, which is responsible for substrate association through hydrogen bonds, and an active ruthenium center, which is in a defined spatial relationship to the oxygenation substrate. DFT calculations illustrate the perfect alignment of the active site with the reactive C-H bond and suggest-in line with the kinetic isotope effect-an oxygen rebound mechanism for the reaction.
Synthesis and cell phototoxicity of a triply bridged fused diporphyrin appended with six thioglucose units
Singh, Sunaina,Aggarwal, Amit,Bhupathiraju, N.V.S. Dinesh K.,Newton, Brandon,Nafees, Ahmad,Gao, Ruomei,Drain, Charles Michael
, p. 6311 - 6314 (2015/01/08)
A triply bridged fused diporphyrin appended with six thioglucose units is reported. This new, chemically, and photochemically stable amphiphilic compound is taken up by breast cancer cells and causes cell death upon light exposure. Photophysical studies r
Synthesis of A2B6-type [36]octaphyrins: Copper(II)-metalation-induced fragmentation reactions to porphyrins and N-fusion reactions of meso-(3-thienyl) substituents
Mori, Hirotaka,Aratani, Naoki,Osuka, Atsuhiro
experimental part, p. 1340 - 1346 (2012/09/08)
5,10,15-Tris(pentafluorophenyl)tetrapyrromethane was efficiently prepared through a route involving stepwise diaroylation of 5- pentafluorophenyldipyrromethane. A2B6-type [36]octaphyrins were prepared by the cross condensation of the
Hydrogen generation by hangman metalloporphyrins
Lee, Chang Hoon,Dogutan, Dilek K.,Nocera, Daniel G.
, p. 8775 - 8777 (2011/07/30)
A cobalt(II) hangman porphyrin with a xanthene backbone and a carboxylic acid hanging group catalyzes the electrochemical production of hydrogen from benzoic and tosic acid in acetonitrile solutions. We show that CoIIH is exclusively involved i
METHODS AND COMPOSITIONS COMPRISING MACROCYCLES
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Page/Page column 10, (2011/06/26)
The present invention relates generally to methods and compositions comprising macrocycles. In some embodiments, the present invention provides methods for modifying macrocycles comprising a pendant group. In some cases, the pendent group comprises a hydrolyzable group. The present invention also provides methods for metallating a macrocycle using microwave energy, in some embodiments.
Efficient synthesis of hangman porphyrins
Dogutan, Dilek K.,Kwabena Bediako,Teets, Thomas S.,Schwalbe, Matthias,Nocera, Daniel G.
supporting information; experimental part, p. 1036 - 1039 (2010/06/15)
Chemical equation presented A two-step synthetic method has been designed to furnish hangman porphyrins In good yields from easily available starting materials. The use of the microwave Irradiation technique has been found to be valuable for delivering the car boxy lie acid hanging group in a much simplified and less time-consuming basic ester hydrolysis (4 h vs 7 days under harsh acidic conditions). The new route facilitates the synthesis of various hangman porphyrins that previously had limited or no access.
Internally 1,4-phenylene-bridged meso aryl-substituted expanded porphyrins: The decaphyrin and octaphyrin cases
Anand, Venkataramanarao G.,Saito, Shohei,Shimizu, Soji,Osuka, Atsuhiro
, p. 7244 - 7248 (2007/10/03)
Current affairs: Incorporation of a 1,4-phenylene bridge into meso aryl-substituted decaphyrin and octaphyrin has a profound impact on the structural and electronic properties of the macrocycles. Bridged decaphyrin has two oxidation states, one of which s
Rational Syntheses of Porphyrins Bearing up to Four Different Meso Substituents
Rao, Polisetti Dharma,Dhanalekshmi, Savithri,Littler, Benjamin J.,Lindsey, Jonathan S.
, p. 7323 - 7344 (2007/10/03)
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.
