ArticleThe Journal of organic chemistry2025
Synthesis of Phenaliporphyrin, a PAH-Porphyrin Hybrid, from an Acenaphthene-Fused Cyclopropane Dialdehyde.
Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Phenaliporphyrin, a new aromatic benziporphyrin derivative, has been synthesized from an annulated cyclopropane dialdehyde intermediate. Corey-Chaykovsky cyclopropanation of dimethyl acenaphthylene-1,2-dicarboxylate gave a cyclopropane diester, and this was converted to the corresponding bis-Weinreb amide. Reduction with lithium aluminum hydride afforded an unstable dialdehyde and subsequent acid-catalyzed condensation with a tripyrrane dicarboxylic acid, followed by oxidation with aqueous ferric chloride, gave the targeted porphyrinoid system. This involves ring expansion of the acenaphthylene precursor to generate the phenalene unit. Phenaliporphyrin exhibits a porphyrin-like UV-vis spectrum with a Soret band at 443 nm and a relatively intense Q-band at 601 nm. The proton NMR spectrum demonstrated that the system has a strong diamagnetic ring current, and the external
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