Electron-Poor Bowl-Shaped Polycyclic Aromatic Dicarboximides: Synthesis, Crystal Structures, and Optical and Redox Properties

Two new bowl-shaped
polycyclic aromatic hydrocarbons, based on
corannulene and naphthalene dicarboximide, are synthesized by an improved
Suzuki–Miyaura cross-coupling and C–H arylation cascade
reaction. Crystallographic analyses confirm structural assignments
and provide insight into molecular interactions in the solid state.
The new bowl-shaped molecules show reversible oxidation and reduction,
intense visible range absorption, and high fluorescence quantum yields.
These molecules can be considered bowl-shaped congeners of planar
perylene dicarboximides.