Internally BN‐Doped Coronene
Abstract
Abstract We present the first synthesis of internally BN‐doped coronenes ( B2N2‐C , H‐B2N2‐C , and 2H‐B2N2‐C ) with two covalent B─N units embedded on the central axis of coronene. The B─N doping leads to unique electronic structures with distinct charge distribution, conjugation, aromaticity, and photophysical properties. The structures were successfully identified by the single‐crystal X‐ray scattering. B2N2‐C without sidechains retains the structure of coronene but exhibits stronger π–π stacking, higher electronic coupling, and a narrowed solid‐state bandgap. Driven by the B─N dipole–dipole interaction, all B2N2‐coronene derivatives exhibit more ordered assembly with excimer emission in solution, which is absent in coronene. Notably, two stable polymorphs emerge in single crystals of 2H‐B2N2‐C with two hexyl chains: a kinetically stable rod phase and a thermodynamically stable plate phase, where variations in processing conditions direct the formation of different phases.
Article Details
Authors (9)
Jing‐Cai Zeng
Beijing National Laboratory for Molecular Sciences (BNLMS) Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education Center of Soft Matter Science and Engineering College of Chemistry and Molecular Engineering Peking University Beijing 100871 P.R. China
Xuan‐Yu Song
Beijing National Laboratory for Molecular Sciences (BNLMS) Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education Center of Soft Matter Science and Engineering College of Chemistry and Molecular Engineering Peking University Beijing 100871 P.R. China
Ze‐Fan Yao
Beijing National Laboratory For Molecular Sciences (BNLMS) Key Laboratory of Polymer Chemistry and Physics of Ministry of Education Center For Soft Matter Science and Engineering College of Chemistry and Molecular Engineering Peking University Beijing China
Yong‐Shi Chen
Beijing National Laboratory of Molecular Sciences (BNLMS) College of Chemistry and Molecular Engineering Peking University Beijing 100871 China
Yu‐Chun Xu
Beijing National Laboratory for Molecular Sciences (BNLMS) Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education Center of Soft Matter Science and Engineering College of Chemistry and Molecular Engineering Peking University Beijing 100871 P.R. China
Kexiang Zhao
Department of Materials Science and Engineering, Institute of Science Tokyo, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan
Yi Liu
Jie‐Yu Wang
Beijing National Laboratory of Molecular Sciences (BNLMS) College of Chemistry and Molecular Engineering Peking University Beijing 100871 China
Jian Pei