Materials featuring mild biradical character have the potential for singlet fission in organic photovoltaics and the application towards organic spin electronics. The formally antiaromatic indenofluorene class of materials has been extensively studied with regard to their electron-accepting ability and photophysics. Here, we report the synthesis and properties of a stable diindenoanthracene derivative. Expanding the indenofluorene scaffold results in a decreased electrochemical gap and a pronounced near-IR absorption. Single crystal X-ray diffraction confirms the closed-shell 2,6-anthraquinodimethane ground state. Variable-temperature NMR and computational studies indicate the presence of a thermally accessible triplet biradical state