title: An Electron-Poor C64 Nanographene by Palladium-Catalyzed Cascade C-C Bond Formation: One-Pot Synthesis and Single-Crystal Structure Analysis.
abstract: Herein, we report the one-pot synthesis of an electron-poor nanographene containing dicarboximide groups at the corners. We efficiently combined palladium-catalyzed Suzuki-Miyaura cross-coupling and dehydrohalogenation to synthesize an extended two-dimensional π-scaffold of defined size in a single chemical operation starting from N-(2,6-diisopropylphenyl)-4,5-dibromo-1,8-naphthalimide and a tetrasubstituted pyrene boronic acid ester as readily accessible starting materials. The reaction of these precursors under the conditions commonly used for Suzuki-Miyaura cross-coupling afforded a C64 nanographene through the formation of ten C-C bonds in a one-pot process. Single-crystal X-ray analysis unequivocally confirmed the structure of this unique extended aromatic molecule with a planar geometry. The optical and electrochemical properties of this largest ever synthesized planar electron-poor nanographene skeleton were also analyzed.
authors.affiliation: Universität Würzburg, Institut für Organische Chemie and Center for Nanosystems Chemistry, Am Hubland, 97074, Würzburg, Germany.
authors.forename: Sabine
authors.initials: S
authors.lastname: Seifert
authors.affiliation: Universität Würzburg, Institut für Organische Chemie and Center for Nanosystems Chemistry, Am Hubland, 97074, Würzburg, Germany.
authors.forename: Kazutaka
authors.initials: K
authors.lastname: Shoyama
authors.affiliation: Universität Würzburg, Institut für Organische Chemie and Center for Nanosystems Chemistry, Am Hubland, 97074, Würzburg, Germany.
authors.forename: David
authors.initials: D
authors.lastname: Schmidt
authors.affiliation: Universität Würzburg, Institut für Organische Chemie and Center for Nanosystems Chemistry, Am Hubland, 97074, Würzburg, Germany. wuerthner@chemie.uni-wuerzburg.de.
authors.forename: Frank
authors.initials: F
authors.lastname: Würthner
keywords: cascade reactions; dyes/pigments; nanographene; polycyclic aromatic hydrocarbons; two-dimensional nanostructures