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

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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.

Details

Original languageEnglish
Pages (from-to)2869-2874
JournalAngewandte Chemie
Volume133
Issue number6
Publication statusPublished - 1 Feb 2021
Peer-reviewedYes

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