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Amethyrin-type expanded porphyrins that display anti-aromatic character upon protonation.

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The use of protonation to switch nonaromatic expanded porphyrins to their corresponding anti-aromatic forms has not been widely explored. Here, we show that free-base pyriamethyrin and dipyriamethyrin display nonaromatic character,… Click to show full abstract

The use of protonation to switch nonaromatic expanded porphyrins to their corresponding anti-aromatic forms has not been widely explored. Here, we show that free-base pyriamethyrin and dipyriamethyrin display nonaromatic character, as inferred from NMR spectroscopic analyses, their optical properties, and theoretical calculations. Addition of two protons extends the π - conjugation of these amethyrin analogues and yields formally anti-aromatic systems.

Keywords: amethyrin type; anti aromatic; expanded porphyrins; type expanded; protonation; character

Journal Title: Chemical communications
Year Published: 2020

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