922142-13-0

Upstream product

• 6018-89-9 nickel(II) acetate tetrahydrate 
• 574735-10-7 [meso-tetraphenyl-2,3-dioxoporphyrinato]nickel^II 
• 221911-02-0 [2,4-diformyl-1,5,10,15-tetraphenylchlorophinato]nickel(II) 
• 203568-12-1 C₄₄H₃₀N₄NiO₂ 
• 917-23-7 5,15,10,20-tetraphenylporphyrin 

Relevant academic research and scientific papers

Meso-arylporpholactones and their reduction products

The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO4--mediated oxidations of the corresponding meso-tetraaryl-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrrole moiety in 1 by an oxazolone moiety. The stepwise reduction of the porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2-oxachlorin (11) and meso-tetraaryl-2-oxachlorins (12). The reactivity of 11 with respect to nucleophilic substitution by O-, N-, and S-nucleophiles is described. The profound photophysical consequences of the formal replacement of a pyrrole with an oxazolone (porphyrin-like chromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochlorin 12, red-shifted Qx band with enhanced oscillator strengths) are detailed and rationalized on the basis of SAC-CI and MNDO-PSDCI molecular orbital theory calculations. The single crystal X-ray structures of the porpholactones point at a minor steric interaction between the carbonyl oxygen and the flanking phenyl group. The essentially planar structures of all chromophores in all oxidation states prove that the observed optical properties originate from the intrinsic electronic properties of the chromophores and are not subject to conformational modulation.

Oxazolochlorins. 2. Intramolecular Cannizzaro reaction of meso-tetraphenylsecochlorin bisaldehyde

(Chemical Equation Presented) Using mildly basic reaction conditions, the periodate-induced diol cleavage of meso-tetraphenyl-2,3-diolchlorin allows for the generation and isolation of the corresponding hitherto elusive free base secochlorin bisaldehyde.

Microwave-promoted insertion of Group 10 metals into free base porphyrins and chlorins: Scope and limitations

The scope and limitations of microwave heating as a tool for insertion of Group 10 metals into meso-tetraphenyl-porphyrin, -porpholactone, and -2,3-dihydroxychlorin derivatives are discussed. In some cases it is possible to reduce reaction times dramatically while obtaining good yields of the metallated products while in others new issues arise relating to the metal salt used as well as acceleration not only of the metallation reaction but also of byproduct formation. The Royal Society of Chemistry.

Elucidation of the extraordinary 4-membered pyrrole ring-contracted azeteoporphyrinoid as an intermediate in chlorin oxidation

Reaction of 2,3-dioxochlorins with benzeneselenic anhydride (BSA) results in the formation of unusual ring-contracted azetine derivatives that further react with BSA to afford porpholactones. The Royal Society of Chemistry.