title: Extended O-Doped Polycyclic Aromatic Hydrocarbons.
abstract: The synthesis of O-doped benzorylenes, in which peripheral carbon atoms have been replaced by oxygen atoms, has been achieved for the first time.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.
authors.affiliation: Namur Research College (NARC), Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, Namur, 5000, Belgium.
authors.forename: Daphné
authors.initials: D
authors.lastname: Stassen
authors.affiliation: Elettra-Sincrotrone Trieste, S.S. 14 Km163.5 in Area Science Park, 34149, Basovizza, Trieste, Italy.
authors.forename: Nicola
authors.initials: N
authors.lastname: Demitri
authors.affiliation: Namur Research College (NARC), Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, Namur, 5000, Belgium. bonifazid@cardiff.ac.uk.|Department of Pharmaceutical and Chemical Sciences and INSTM UdR Trieste, University of Trieste, Piazzale Europa 1, Trieste, 34127, Italy. bonifazid@cardiff.ac.uk.|School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK. bonifazid@cardiff.ac.uk.
authors.forename: Davide
authors.initials: D
authors.lastname: Bonifazi
keywords: copper; cyclization; macromolecules; nanostructures; supramolecular chemistry