Chemical Oxidation Induced Aromaticity Switching of <i>E</i>‑Ethylene Bridged [38] Octaphyrin (1.2.1.0.1.2.1.0)\nwith NIR Absorption

We report the syntheses, spectroscopic\nanalyses, and solid-state\nstructural evidence of a quasi-planar aromatic [38] <i>E</i>-ethylene bridged octaphyrin (1.2.1.0.1.2.1.0) exhibiting NIR absorption.\nThe chemical oxidation using an appropriate oxidant led to unique\nπ reconstruction via amine-imine conversion and/or C-oxygenation\nof the inverted thiophene rings resulting in weakly antiaromatic or\nnonaromatic [36] octaphyrins with preserved <i>E</i>-conformation\nof the ethylene moieties. The aromatic nature of the studied octaphyrins\nis supported by GIMIC calculations of the magnetically induced ring\ncurrent density.