An Electron-Poor C64 Nanographene by Palladium-Catalyzed Cascade C−C Bond Formation: One-Pot Synthesis and Single-Crystal Structure Analysis

详细信息    查看全文

• 作者：Sabine Seifert ; Dr. Kazutaka Shoyama ; Dr. David Schmidt and Prof. Dr. Frank Wü ; rthner
• 刊名：Angewandte Chemie
• 出版年：2016
• 出版时间：May 23, 2016
• 年：2016
• 卷：128
• 期：22
• 页码：6500-6505
• 全文大小：3629K
• ISSN：1521-3757

文摘

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.