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One‐Pot Synthesis of Boron‐Doped Polycyclic Aromatic Hydrocarbons via 1,4‐Boron Migration
Author(s) -
Zhang JinJiang,
Tang ManChung,
Fu Yubin,
Low KamHung,
Ma Ji,
Yang Lin,
Weigand Jan J.,
Liu Junzhi,
Yam Vivian WingWah,
Feng Xinliang
Publication year - 2021
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.202011237
Subject(s) - boron , doping , chemistry , materials science , environmental chemistry , nanotechnology , organic chemistry , optoelectronics
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.