Trichalcogenasumanene ortho ‐Quinones: Synthesis, Properties, and Transformation into Various Heteropolycycles

The regioselective transformation of heterobuckybowl trichalcogenasumanenes 1 a , b at peripheral butoxy groups afforded trichalcogenasumanene ortho ‐quinones 2 a , b . Compounds 2 a , b are distinct from 1 a , b in terms of their molecular geometry and electronic state; that is, they have a shallower bowl depth and show absorbance in the NIR region. The reaction of 2 a , b with diamines resulted in a variety of heteropolycycles, including molecular spoon 3 a – 6 a , planar π‐systems 3 b – 6 b , and highly twisted [7‐6‐6]‐fused systems 7 a , b . These new heteropolycycles had different optical/electrical properties: 4 a,b showed hole mobility of approximately 0.002 cm 2  V −1  s −1 , 6 a displayed red emission in both solution and the solid state, and 7 a , b formed tight stacks of the curved π‐surface.