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The synthesis of open‐shell polycyclic hydrocarbons with large diradical characters is challenging because of their high reactivities. Herein, two diindeno‐fused corannulene regioisomers DIC‐1 and DIC‐2, curved fragments of fullerene C104, were synthesized that exhibit open‐shell singlet ground states. The incorporation of the curved and non‐alternant corannulene moiety within diradical systems leads to significant diradical characters as high as 0.98 for DIC‐1 and 0.89 for DIC‐2. Such high diradical characters can presumably be ascribed to the re‐aromatization of the corannulene π system. Although the DIC compounds have large diradical characters, they display excellent stability under ambient conditions. The half‐lives are 37 days for DIC‐1 and 6.6 days for DIC‐2 in solution. This work offers a new design strategy towards diradicaloids with large diradical characters yet maintain high stability. [ABSTRACT FROM AUTHOR]

Abstract: A pair of interconvertible stereoisomers of imide‐fused corannulene derivatives was mixed with C60, which resulted in cocrystallization into a 1:1 segregated packing motif through concave–convex π–π interactions. Only one conformation was observed in the cocrystal owing to guest‐induced conformational switching. The 1D assemblies of the complex showed promising applications in organic electronics. [ABSTRACT FROM AUTHOR]