Extended O-Doped Polycyclic Aromatic Hydrocarbons

D. Stassen, N. Demitri, D. Bonifazi,
Angew. Chem., Int. Ed., 2016, 55, 5947-5951
DOI: 10.1002/anie.201509517


The synthesis of O-doped benzorylenes, in which peripheral carbon atoms have been replaced by oxygen atoms, has been achieved for the first time.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 favourable solid-state arrangement for organic electronics.

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