5,4′-Bis[bis(methoxyphenyl)amino]-2-methoxystilbene and its cationic biradical

5,4′-Bis[bis(p-methoxyphenyl)amino]-2-methoxystilbene (1) was synthesized. The electrochemical and chemical oxidations of 1 produced its cationic biradical, which was studied in comparison with the biradical derived from the analogue 2 without the 2-methoxy substituent. The biradical of 1 exhibited substantial chemical stability, because the reactive 2-position of a 5,4′-biradical-substituted stilbene is effectively blocked in 1 with the methoxy substituent. However, the 2-substituent caused a torsion in the stilbenoid π-conjugated framework to weaken its ferromagnetic coupling ability.