期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2021, 期 9, 页码 1440-1445出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202001672
关键词
Lewis acids; Organoboron chemistry; Sterically hindered compounds; Triptycenes
资金
- University of Namur
- Namur Institute of Structured Matter (NISM)
- FNRS [F.4513.18, 1.B.087.21F, 1.E.097.20F]
Two synthetic strategies were developed to synthesize triptycene-derived bulky boranes, boronates, and boron ate-complexes with various boron substituents. The study showed the quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds through single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements.
We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF3K and B(Mes)(2). Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.
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