An electron-poor C\(_{64}\) nanographene by palladium-catalyzed cascade C-C bond formation: one-pot synthesis and single-crystal structure analysis

Please always quote using this URN: urn:nbn:de:bvb:20-opus-188889
  • 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 pi-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 usedHerein, 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 pi-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 C\(_{64}\) 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.show moreshow less

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Metadaten
Author: Sabine Seifert, Kazutaka Shoyama, David Schmidt, Frank WürthnerORCiDGND
URN:urn:nbn:de:bvb:20-opus-188889
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Organische Chemie
Language:English
Parent Title (English):Angewandte Chemie-International Edition
Year of Completion:2016
Volume:55
Issue:22
Pagenumber:6390-6395
Source:Angewandte Chemie-International Edition (2016) 55:22, 6390-6395. https://doi.org/10.1002/anie.201601433
DOI:https://doi.org/10.1002/anie.201601433
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 547 Organische Chemie
Tag:Aromatic-hydrocarbon; Carbon; Dyes; Functionalization; Graphene nanoribbons; Liquid-crystalline; cascade reactions; dyes/pigments; nanographene; polycyclic aromatic hydrocarbons; two-dimensional nanostructures
Release Date:2020/06/02
Licence (German):License LogoCC BY-NC-ND: Creative-Commons-Lizenz: Namensnennung, Nicht kommerziell, Keine Bearbeitungen 4.0 International