A 24 π-electron antiaromatic hexaphyrin derivative (rosarin) with a near-planar geometry enforced by bridging phenylene groups has been shown to undergo a proton-coupled electron transfer reduction when treated with certain protic acids. The reduction proceeds in a stepwise fashion to give first a 25 π-electron non-aromatic system and then a 26 π-electron aromatic ring.
- Masatoshi Ishida
- Soo-Jin Kim
- Jonathan L. Sessler
