Concise Synthesis of BN-Dibenzo[f,k]tetraphenes with Different BN Substitution Positions and Direct Comparison with Their Carbonaceous Analogue

Two types of “parental” BN-dibenzo­[f,k]­tetraphenes (BNDBT-1 and BNDBT-2) have been synthesized via a transition-metal-catalyzed tandem cross-coupling reaction as key steps. Both BNDBT-1 and BNDBT-2 are fully characterized; one of them is unambiguously confirmed by a single X-ray crystal structure....

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Bibliographic Details
Published in:Journal of organic chemistry 2022-05, Vol.87 (10), p.6630-6637
Main Authors: Xu, Xiaoyang, Jin, Mengjia, Jiang, Ruijun, Zhang, Lei, Wu, Xiaoming, Liu, Xuguang
Format: Article
Language:English
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Summary:Two types of “parental” BN-dibenzo­[f,k]­tetraphenes (BNDBT-1 and BNDBT-2) have been synthesized via a transition-metal-catalyzed tandem cross-coupling reaction as key steps. Both BNDBT-1 and BNDBT-2 are fully characterized; one of them is unambiguously confirmed by a single X-ray crystal structure. Compared to its all-carbon analogue DBT, BNDBT-1 and BNDBT-2 exhibit a higher highest occupied molecular orbital (HOMO) and lower lowest unoccupied molecular orbital (LUMO) energy, while the BN doping position slightly influences the HOMO and LUMO energies of BNDBT-1 and BNDBT-2. Both BNDBT-1 and BNDBT-2 exhibit red-shifted absorption and emission spectra and higher emission efficiencies, as compared to their carbonaceous analogue DBT. Moreover, organic light emitting diodes were fabricated using BNDBT-1 and BNDBT-2 as emitters, demonstrating their potential applications.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00278