期刊
CHEMICAL SCIENCE
卷 12, 期 22, 页码 7943-7952出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc02065j
关键词
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资金
- Deutsche Forschungsgemeinschaft (DFG) [MI 477/25-3, 248859450, SPP1807, MI477/28-2, 271386299]
In this study, 1,8-dialkynylanthracene photo-dimers were prepared in head-to-head configuration using 2-hydroxypropyl-protecting groups and demonstrated their applicability as a building block for a tetradentate boron Lewis acid. The formation of adducts with various nitrogen bases showed the potential of the compound as a host for Lewis-base substrates, with impressive networks formed between the tetraboron host and the substrate molecules in the case of adduct formation with hydrazine.
Using 2-hydroxypropyl-protecting groups, 1,8-dialkynylanthracene photo-dimers were prepared in head-to-head-configuration by UV irradiation on a multi-gram scale. In non-polar solvents, the combination of non-covalent hydrogen bonds and pi-pi-interactions induces the formation of the syn-isomer in up to 85% yield. Instead, more polar solvents or irradiation of unprotected 1,8-diethynylanthracene led to formation of the corresponding anti-isomer in large excess. Cleavage of the protecting groups under basic conditions affords a rigid hydrocarbon skeleton with four directional functions. This was used as a building block for a tetradentate boron Lewis acid. Its applicability as a host for Lewis-base substrates was demonstrated by the formation of adducts with various nitrogen bases. Adduct formation with hydrazine leads to impressive networks between the tetraboron host and the substrate molecules.
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