These IRC results show that the scavenging of O2 •-by PiceH4 in DMF is governed by 2PCET at the catechol moiety after the formation of PRC between PiceH4 and O2 •-. Notably, the coplanar stilbene moiety kinetically promotes 2PCET at the catechol moiety, where the two rings of PiceH4 linked by the double bond of stilbene expand the π-conjugated plane, demonstrating successful scavenging of O2 •-.