One‐Pot Synthesis of Boron‐Doped Polycyclic Aromatic Hydrocarbons via 1,4‐Boron Migration

• Published in: Angewandte Chemie Vol. 133; no. 6; pp. 2869 - 2874
• Main Authors: Zhang, Jin‐Jiang, Tang, Man‐Chung, Fu, Yubin, Low, Kam‐Hung, Ma, Ji, Yang, Lin, Weigand, Jan J., Liu, Junzhi, Yam, Vivian Wing‐Wah, Feng, Xinliang
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 08.02.2021
• Subjects: 1,4-boron migration; Aromatic compounds; Atom economy; Boron; boron doping; Chemistry; Crystallography; Fluorescence; nanographenes; Optoelectronics; organic electronics; Polycyclic aromatic hydrocarbons; polycyclic aromatic hydrocarbons (PAHs); Reaction mechanisms; Substrates
• ISSN: 0044-8249; 1521-3757
• DOI: 10.1002/ange.202011237

Herein, we demonstrate a novel one‐pot synthetic method towards a series of boron‐doped polycyclic aromatic hydrocarbons (B‐PAHs, 1 a–1 o), including hitherto unknown B‐doped zethrene derivatives, from ortho‐aryl substituted diarylalkynes with high atom efficiency and broad substrate scopes. A reaction mechanism is proposed based on the experimental investigation together with the theoretical calculations, which involves a unique 1,4‐boron migration process. The resultant benchtop‐stable B‐PAHs are thoroughly investigated by X‐ray crystallography, cyclic voltammetry, UV/Vis absorption, and fluorescence spectroscopies. The blue and green organic light‐emitting diode (OLED) devices based on 1 f and 1 k are further fabricated, demonstrating the promising application potential of B‐PAHs in organic optoelectronics. A novel one‐pot synthetic strategy towards a series of boron‐doped polycyclic aromatic hydrocarbons from ortho‐aryl substituted diarylalkynes has been developed. A reaction mechanism is proposed based on the experimental investigation together with the theoretical calculations, which involves an unprecedented 1,4‐boron migration process.