One‐Pot Synthesis of Boron‐Doped Polycyclic Aromatic Hydrocarbons via 1, 4‐Boron Migration. Issue 6 (9th December 2020)

• Record Type: Journal Article
• 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
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 6(2021)
• Page Start: 2833
• Page End: 2838
• Publication Date: 2020-12-09
• Subjects: 1, 4-boron migration -- boron doping -- nanographenes -- organic electronics -- polycyclic aromatic hydrocarbons (PAHs); Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202011237
• Languages: English
• ISSNs: 1433-7851

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. Abstract : 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.