Aromaticity Relocation in Perylene Derivatives upon Two‐Electron Oxidation To Form Anthracene and Phenanthrene. Issue 41 (12th August 2016)

• Record Type: Journal Article
• Authors: Matsumoto, Akinobu; Suzuki, Mitsuharu; Hayashi, Hironobu; Kuzuhara, Daiki; Yuasa, Junpei; Kawai, Tsuyoshi; Aratani, Naoki; Yamada, Hiroko
• Is Part Of: Chemistry. Volume 22:Issue 41(2016)
• Page Start: 14462
• Page End: 14466
• Publication Date: 2016-08-12
• Subjects: aromaticity -- bond length alternation -- dication -- oxidation -- perylene; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201602188
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: We prepared perylene dications1 2+ and2 2+ by using "capped" perylene derivatives, and for the first time, successfully obtained single crystals of a perylene dication1 2+ that enabled us to perform its structural analysis. We realized that the substituted aryl groups on perylene control the positions of positive charges, thus the remaining electronic system satisfies Clar's sextet rule toward the highest number of localized sextets. Experimental and theoretical evidence proved that Clar's aromatic π‐sextet rule could be applied even for the dicationic perylenes in a very simple way. Abstract : Charging double : Perylene dications1 2+ and2 2+ by using "capped" perylene derivatives were prepared (see figure), and the single crystal of a perylene dication, 1 2+, was successfully obtained for the first time. Experimental and theoretical evidence proved that Clar's aromatic π‐sextet rule can be applied even for the dicationic perylenes in a very simple way.