852244-71-4

Upstream product

• 98-88-4 benzoyl chloride 
• 99840-54-7 5,5'-dimethyldipyrromethane 
• 10002-30-9 S-pyridin-2-yl benzenecarbothioate 

Downstream Products

• 1026001-93-3 {5-[1-methyl-1-(1H-pyrrol-2-yl)-ethyl]-1H-pyrrol-2-yl}-phenyl-methanol 

Relevant academic research and scientific papers

Photoinduced Dynamics of Bis-dipyrrinato-palladium(II) and Porphodimethenato-palladium(II) Complexes: Governing Near Infrared Phosphorescence by Structural Restriction

Although superficially similar, the bis-dipyrrinato-palladium(II) complex 1 and the bridged porphodimethenato-palladium(II) complex 2 possess dramatically different structures in the ground state (proved by X-ray structure analysis) and in the singlet and

Direct synthesis of palladium porphyrins from acyldipyrromethanes

(Chemical Equation Presented) Palladium porphyrins are valuable photosensitizers and luminescent agents in biology and materials chemistry. New methodology is described wherein a 1-acyldipyrromethane is converted into the palladium chelate of a trans-A2B2 porphyrin via a one-flask reaction. The reaction entails self-condensation of the 1-acyldipyrromethane in refluxing ethanol containing KOH (5-10 mol equiv) and Pd(CH3CN)2Cl2 (0.6 mol equiv) exposed to air. This direct route to palladium porphyrins is more expedient than the four steps of the traditional synthesis: (1) reduction of the 1-acyldipyrromethane; (2) acid-catalyzed condensation; (3) oxidation of the porphyrinogen intermediate; and (4) metal insertion. The new synthesis requires neither acid nor DDQ and formally entails only a 2e- + 2H+ oxidation overall versus the traditional multistep synthesis which requires a 2e- + 2H + reduction per each 1-acyldipyrromethane (4e- + 4H + overall) followed by a 6e- + 6H+ oxidation. The analogous reaction of a 1,9-diacyldipyrromethane and a dipyrromethane also gives the palladium porphyrin. Seven palladium porphyrins have been prepared in yields of 25-57%. The direct route also can be used with Cu(OAc) 2·H2O to give the copper porphyrin albeit in low yield. In summary, this methodology readily affords palladium porphyrins directly from acyldipyrromethanes.