Synthesis, Structure, and Properties of Two Planar BN-Benzofluorenes
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Updated: May 16, 2025

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Published on: March 25, 2017
Guan Wang1, Qianqian Guo1, Yue Xin1
1Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China.
Abstract:
Two planar BN doped benzofluorenes (BN-BkF and BN-BjF) were synthesized separately through palladium-catalyzed intramolecular C-C or C-N coupling reactions. The structures of both BN-BkF and BN-BjF are unambiguously confirmed by X-ray crystallographic analysis. Moreover, the BN unit doping leads to a much lower HOMO level and higher LUMO level as compared to their carbon analogues BkF and BjF. In comparison to BkF and BjF, both BN-BkF and BN-BjF exhibit blue shifts in their ultraviolet-visible (UV-vis) absorption and fluorescence emission spectra. Furthermore, halogenation of BN-BkF and BN-BjF afforded monohalogenated BN-benzofluorenes in good yields. These monohalogenated BN-benzofluorenes can serve as convenient intermediates for palladium-catalyzed coupling reactions to yield a series of functionalized BN-benzofluorene derivatives. The UV-vis absorption and emission spectroscopies in dichloromethane of these BN-benzofluorene derivatives were studied, and the photophysics of these compounds exhibited a high degree of substituent dependency.
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