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An Electron‐Poor C 64 Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis
Author(s) -
Seifert Sabine,
Shoyama Kazutaka,
Schmidt David,
Würthner Frank
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201601433
Subject(s) - palladium , catalysis , materials science , crystal structure , molecule , dehydrohalogenation , pyrene , one pot synthesis , crystallography , combinatorial chemistry , chemistry , organic chemistry
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 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.