One‐Pot Synthesis of Boron‐Doped Polycyclic Aromatic Hydrocarbons via 1,4‐Boron Migration
Jinjiang Zhang, Man‐Chung Tang, Yubin Fu, Kam‐Hung Low, Ji Ma, Lin Yang, Jan J. Weigand, Junzhi Liu, Vivian Wing‐Wah Yam, Xinliang Feng
Abstract
Abstract 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.