氧化对硫桥联联萘二聚体手性光学性质的影响。
Effect of Oxidation on the Chiroptical Properties of Sulfur-Bridged Binaphthyl Dimers.
作者信息
Yuan Jennifer, Jiang Lanting, Nishimura Tatsuya, Sauvé Ethan R, Hean Duane, Maeda Katsuhiro, Wolf Michael O
机构信息
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1.
Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
出版信息
J Org Chem. 2022 Sep 16;87(18):12315-12322. doi: 10.1021/acs.joc.2c01516. Epub 2022 Sep 6.
A series of axially chiral sulfur-bridged dimers were prepared from 1,1'-binaphthyl-2,2'-diol and subsequently oxidized to the respective sulfones. The chiroptical properties of the chiral chromophores were studied as a function of the oxidation state. Upon oxidation, an increase in quantum yields was observed for directly linked sulfur bridged binaphthyls (0.04 to 0.32), and a modest increase in dissymmetry factor was observed for diphenylsulfide-bridged binaphthyls (-8.9 × 10 to -1.4 × 10). Computational calculations were used to elucidate the changes in photophysical properties.
一系列轴向手性硫桥联二聚体由1,1'-联萘-2,2'-二醇制备而成，随后被氧化为相应的砜。研究了手性发色团的圆二色性性质与氧化态的关系。氧化后，直接连接的硫桥联联萘（量子产率从0.04提高到0.32）的量子产率增加，而二苯硫醚桥联联萘（不对称因子从-8.9×10提高到-1.4×10）的不对称因子有适度增加。采用计算计算来阐明光物理性质的变化。
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