Expanded isophlorins are typical examples for stable anti-aromatic systems. Paratropic ring current effects are observed in their NMR spectra mainly due to their planar conformation. Herein we report the synthesis of the first twisted 40π expanded isophlorin and also its two-electron oxidation to a 38π dication. It sustains the twisted conformation for the 4nπ and (4n+2)π electrons. Due to the non-planar conformation, they do not display ring current effects in their respective 1H NMR spectrum. NICS calculations reveal the non-(anti)aromatic features for the neutral 40π and the 38π dication species.
