title: Air- and heat-stable planar tri-p-quinodimethane with distinct biradical characteristics.
abstract: A heptacyclic carbocycle possessing three p-quinodimethane units conjugated in one plane has been synthesized and shown to exhibit distinct biradical characteristics. The molecule has a HOMO/LUMO band gap of ca. 1 eV and a S(0)-T(1) energy gap of 2.12 kcal/mol, and it absorbs and emits near-IR light at room temperature. It is air-stable under ambient light for several months and thermally stable up to 160 °C under nitrogen, and it undergoes reversible two-electron oxidation and reduction. The synthetic approach is such that a smaller and larger oligo-p-quinodimethane can be synthesized.
authors.affiliation: Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Xiaozhang
authors.initials: X
authors.lastname: Zhu
authors.forename: Hayato
authors.initials: H
authors.lastname: Tsuji
authors.forename: Koji
authors.initials: K
authors.lastname: Nakabayashi
authors.forename: Shin-ichi
authors.initials: S
authors.lastname: Ohkoshi
authors.forename: Eiichi
authors.initials: E
authors.lastname: Nakamura
mesh_terms: D000388:Air; D016576:Fleroxacin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D006358:Hot Temperature; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005609:Free Radicals; D009570:Nitriles; C569644:tri-p-quinodimethane; D016576:Fleroxacin