title: Tetrabenzo[a,f,j,o]perylene: a polycyclic aromatic hydrocarbon with an open-shell singlet biradical ground state.
abstract: A novel tetrabenzo[a,f,j,o]perylene, namely "bistetracene" in which two tetracenes are connected side by side with two bonds, was synthesized and characterized. An optical energy gap of about 1.56 eV is derived from the UV/Vis absorption spectrum, showing the low optical gap feature of such zigzag-edged polycyclic aromatic hydrocarbons (PAHs). Theoretical calculations and physical property investigations manifest that such a PAH possesses a prominent biradical character in the ground state, which is the first example among bistetracene derivatives. However, the bistetracene can easily undergo oxidation to tetrabenzo[a,f,j,o]perylene-9,19-dione (diketone) under ambient conditions. Thereby, such zigzag-edged PAH provides insight into understanding the edge state of other expanded homologues, such as peri-tetracenes or peri-pentacenes.
authors.affiliation: Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany).
authors.forename: Junzhi
authors.initials: J
authors.lastname: Liu
authors.affiliation: Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany).
authors.forename: Prince
authors.initials: P
authors.lastname: Ravat
authors.affiliation: Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany).
authors.forename: Manfred
authors.initials: M
authors.lastname: Wagner
authors.affiliation: Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany).
authors.forename: Martin
authors.initials: M
authors.lastname: Baumgarten
authors.affiliation: Center for Advancing Electronics Dresden (cfaed) and Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden (Germany). xinliang.feng@tu-dresden.de.
authors.forename: Xinliang
authors.initials: X
authors.lastname: Feng
authors.affiliation: Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany). muellen@mpip-mainz.mpg.de.
authors.forename: Klaus
authors.initials: K
authors.lastname: Müllen
keywords: biradical; bistetracene; perylenes; polycyclic arenes; zigzag-edge