Synthesis and Characterization of Brominated Derivatives of 9,10-BN-Naphthalene as Versatile Building Blocks for
Yanli Zhang1, Xiangshuai Du1, Qian Wu1
1State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Academy for Advanced Interdisciplinary Studies, and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, 38 Tongyan Road, Jinnan District, Tianjin 300350, China.
Abstract:
Boron-nitrogen (BN) units are valuable structural motifs for modulating the photoelectric properties of π-conjugated systems. In this work, we report the synthesis and structural elucidation of a series of brominated 9,10-BN-naphthalene derivatives that serve as versatile intermediates for subsequent cross-coupling functionalization. Controlled bromination afforded mono- to poly brominated species, including two distinct tribrominated regioisomers that enabled diverse derivatization pathways. Through Suzuki-Miyaura reactions, a range of multiarylated 9,10-BN-naphthalenes were obtained, significantly expanding the structural diversity of BN-embedded aromatic frameworks. The resulting compounds were characterized by NMR spectroscopy, DFT calculations, and single-crystal X-ray diffraction for selected examples. Their photophysical properties revealed substituent-dependent variations in absorption and emission profiles, highlighting the tunable electronic nature of the BN-doped propeller-shaped molecules. This study establishes an efficient and modular approach for diversifying BN-naphthalene scaffolds and deepens understanding of their structure-property relationships.
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