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Synthesis of Pyrrole‐Sharing Fused Porphyrinoid Hybrids by Post‐fabrication of Ni(II) Porphyrins

Lili Zi, Li Liu, Mingbo Zhou, Le Liu, Boyu Xiao, Ling Xu, Yutao Rao, Bangshao Yin, Jianxin Song, Atsuhiro Osuka

2023Angewandte Chemie International Edition14 citationsDOIOpen Access PDF

Abstract

Abstract Pyrrole‐sharing fused hybrids of Ni II porphyrin with Pd II N‐confused(NC)‐corrole and Pd II NC‐oxaporphyrin were synthesized by post‐fabrication of Ni II porphyrins. Specifically this consists of Friedel–Crafts type aromatic substitution reaction of meso ‐free Ni II porphyrin with α , α ′‐dibromotripyrrin and Pd(OAc) 2 assisted cyclization, and final heating to induce a Pd−C bond formation. Ni II porphyrins fused with Pd II NC‐corrole and with Pd II NC‐oxaporphyrins show coplanar structures with a shared pyrrole unit. In these hybrids, the Pd II NC‐oxaporphyrin is aromatic and the Pd II NC‐corrole is moderately antiaromatic and these local electronic properties interact to influence the whole network.

Topics & Concepts

CorrolePorphyrinPyrroleChemistryAntiaromaticityPhotochemistryAromaticityPalladiumCrystallographyPolymer chemistryMoleculeOrganic chemistryCatalysisPorphyrin and Phthalocyanine ChemistryPorphyrin Metabolism and DisordersSurface Chemistry and Catalysis
Synthesis of Pyrrole‐Sharing Fused Porphyrinoid Hybrids by Post‐fabrication of Ni(II) Porphyrins | Litcius