Corannurylene Pentapetalae

Despite
the great advances in the synthesis of diverse nonplanar
graphenoids, investigations into the relationship between structural
features and intermolecular interactions still present significant
challenges. Herein, the novel nonplanar graphenoid structure, corannurylene
pentapetalae (CRP), obtained via bottom-up syntheses of hybridization
between perylene diimide (PDI) planar fragments and a corannulene
curved core, is presented. Single crystal studies reveal a D5-symmetric as well as a C2-symmetric graphenoid corannurylene pentapetalae. The D5-symmetric structure has a unique honeycomb
lattice with two chiral honeycomb layers alternately stacked, whereas
the C2-symmetric CRP forms dimer units
via π–π stacking. Transistor devices demonstrate
that, without any π–π stacking, the honeycomb lattice
of the D5-symmetric CRP has the potential
to also facilitate electron transport.