Jin-Jiang Zhang1, Man-Chung Tang2, Yubin Fu1, Kam-Hung Low2, Ji Ma1, Lin Yang1, Jan J Weigand3, Junzhi Liu2,4, Vivian Wing-Wah Yam2, Xinliang Feng1. 1. Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062, Dresden, Germany. 2. Institute of Molecular Functional Materials and Department of Chemistry, The University of Hong Kong, Rokfulam Road, Hong Kong, P. R. China. 3. Chair of Inorganic Molecular Chemistry & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062, Dresden, Germany. 4. State Key Laboratory of Synthetic Chemistry and Department of Chemistry, The University of Hong Kong, Rokfulam Road, Hong Kong, P. R. China.
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.
Herein, we demonstrate a novel one-pot synthetic method towards a series of boron-dopedpan> class="Chemical">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.
Authors: Ana Milián; Manuel A Fernández-Rodríguez; Estíbaliz Merino; Juan J Vaquero; Patricia García-García Journal: Angew Chem Int Ed Engl Date: 2022-05-24 Impact factor: 16.823