Extended O-Doped Polycyclic Aromatic Hydrocarbons

a) SEM images of polyaromatic molecular crystals displaying a lamellar-like texture; b) solid-state columnar π-π stacks with an interplanar distance of 3.3Å

Stassen D. et al., Angew. Chem. 2016, 128, 1 – 6

The synthesis of O-doped benzorylenes, in which peripheral carbon atoms have been replaced by oxygen atoms, has been achieved for the first time. This includes key high-yielding ring-closure steps which, through intramolecular C-O bond formation, allow stepwise planarization of oligonaphthalenes. Single-crystal X-ray diffraction showed that the tetraoxa derivative forms remarkable face-to-face π–π stacks in the solid state, a favorable solid-state arrangement for organic electronics.

Retrieve Article Extended O-Doped Polycyclic Aromatic Hydrocarbons; Stassen D., Demitri N., Bonifazi D., Angew. Chem. 2016, 128, 1 – 6 doi: 10.1002/ange.201509517