TY  - JOUR
A1  - Seifert, Sabine
A1  - Shoyama, Kazutaka
A1  - Schmidt, David
A1  - Würthner, Frank
T1  - An electron-poor C\(_{64}\) nanographene by palladium-catalyzed cascade C-C bond formation: one-pot synthesis and single-crystal structure analysis
JF  - Angewandte Chemie-International Edition
N2  - 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 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.
KW  - Graphene nanoribbons
KW  - Liquid-crystalline
KW  - dyes/pigments
KW  - polycyclic aromatic hydrocarbons
KW  - two-dimensional nanostructures
KW  - Aromatic-hydrocarbon
KW  - Carbon
KW  - Dyes
KW  - Functionalization
KW  - cascade reactions
KW  - nanographene
Y1  - 2016
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-188889
VL  - 55
IS  - 22
ER  -