Phenanthrene-Incorporated Isoamethyrin: A Near-Planar Macrocycle That Display Enhanced Aromaticity via Protonation-Triggered Conformation Changes.

Controlling the aromaticity in expanded porphyrins is a forefront research topic, and the strategy of using protonation-triggered conformational changes to fine-tune electronic properties and aromaticity has yet to be generalized in rigid and planar expanded porphyrins. Here, we synthesized phenanthrene-incorporated isoamethyrins that possess near-planar conformations and nonaromatic characters. However, when methanesulfonic acid (MSA) was added, geometric deformations occurred to minimize the unfavorable strain, resulting in macrocycles that were weakly aromatic as a whole.