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Article Abstract
Novel nickel(II) and copper(II) complexes of 2-(,-dimethylformamidine)-3-formyl-5,10,15,20-tetraarylporphyrins have been synthesized for the first time from 2-aminoporphyrins under Vilsmeier-Haack conditions. These porphyrins are utilized as new building blocks to construct diverse β-pyrimidine-fused 5,10,15,20-tetraarylporphyrins in good yields a cascade ammonia-mediated condensation and intramolecular aza-6π-annulation/aromatization in 1,2-dichloroethane at 80 °C. Furthermore, copper(II) β-pyrimidine-fused porphyrins underwent demetallation in the presence of conc. HSO to afford free-base porphyrins, which on zinc insertion using Zn(OAc) in CHCl-MeOH provided zinc(II) β-pyrimidine-fused porphyrins in appreciable yields. Notably, these newly synthesized π-extended porphyrins displayed a modest bathochromic shift in their electronic absorption and emission spectra as compared to the traditional -tetraarylporphyrins. However, the protonated porphyrins () and () displayed a significant red-shifted absorption.
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