Bisindeno Fusion on the Zigzag Edge of Bis(benzooxa)-2,6-anthraquinodimethane: Effect on Diradical Character, Photostability, and Redox Properties.

We report the synthesis of the bis(benzooxa)-2,6-anthraquinodimethane ( BAQ ) derivative and its bisindeno fused analogue BIBAQ . We found bisindeno fusion on the quinoidal zigzag edge of BAQ results in decreased diradical character and corresponding increased photostability. Furthermore, BAQ could only be oxidized into its cationic species, while BIBAQ showed balanced redox properties.