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

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.

SUBMITTER: Zhang JJ

PROVIDER: S-EPMC7898796 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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

Zhang Jin-Jiang JJ Tang Man-Chung MC Fu Yubin Y Low Kam-Hung KH Ma Ji J Yang Lin L Weigand Jan J JJ Liu Junzhi J Yam Vivian Wing-Wah VW Feng Xinliang X

Angewandte Chemie (International ed. in English) 20201209 6

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 ...[more]

PMID: 33112494

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