193265-41-7Relevant academic research and scientific papers
Insights into the Synthesis and the Solution Behavior of meso-Aryloxy- and Alkoxy-Substituted Porphyrins
Birin, Kirill P.,Gorbunova, Yulia G.,Tsivadze, Aslan Yu.,Bessmertnykh-Lemeune, Alla G.,Guilard, Roger
, p. 5610 - 5619 (2015)
meso-RO-appended (R = alkyl, aryl) porphyrins bearing one or two OR substituents at the tetrapyrrolic macrocycle were synthesized in good yields from 5,15-dibromo-10,20-diphenylporphyrins 2H(Br2DPP), Ni(Br2DPP) and Zn(Br2DPP) using an SNAr reaction. By varying the solvent, the base, the temperature, and the time of the reaction, the optimum conditions were established, and the selective introduction of one or two meso-RO substituents at the periphery of the macrocycle was achieved. Moreover, monofunctionalization of Ni(Br2DPP) according to an SNAr reaction was used as a key step for the synthesis of rarely explored unsymmetrical porphyrinyl alkyl ethers. 1H NMR studies of these ethers in CDCl3 revealed concentration-dependent aggregation of the zinc derivative through coordination of the central metal ion of one molecule to the peripheral oxygen atom of a second tetrapyrrolic macrocycle.
Functionalization of 5,15-diphenylporphyrin: Preparation and X-ray crystal structures of meso nitro, bromo, and trimethylsilylethynyl derivatives
Arnold, Dennis P.,Bott, Raymond C.,Eldridge, Helen,Elms, Fiona M.,Smith, Graham,Zojaji, Mike
, p. 495 - 503 (2007/10/03)
Substitutions on 5,15-diphenylporphyrin led to the isolation of mono- and di-bromo and mono- and di-nitro derivatives, which were converted into their respective nickel(II) complexes. Reaction of the bromoporphyrins with iodine/silver nitrite resulted in nitrodebromination as well as conventional nitration. The nickel (II) complex of 5-nitro-10,20-diphenylporphyrin was reduced to the 5-amino derivative. The nickel(II) complexes of the bromoporphyrins were converted into the respective mono- and bis-(trimethylsilylethynyl) species. The crystal structures of 5-nitro-10,20-diphenylporphyrin, 5-bromo-10,20-diphenylporphyrinatonickel(II), and 10,20-diphenyl-5-(trimethylsilylethynyl)porphyrinatonickel(II) were determined.
