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.
               
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