Two new expanded porphyrins, naphthorubyrin and naphthosapphyrin, were synthesized. The π-extended rubyrin was isolated and structurally characterized in its monoprotonated form. The sapphyrin congener undergoes pyrrole inversion as a function of the protonation state. These conformational effects are reflected in the spectroscopic features, including the excited singlet state lifetimes.
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