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Effect of Oxidation on the Chiroptical Properties of Sulfur-Bridged Binaphthyl Dimers. 2022
Jennifer Yuan, and
Lanting Jiang, and
Tatsuya Nishimura, and
Ethan R Sauvé, and
Duane Hean, and
Katsuhiro Maeda, and
Michael O Wolf
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1.
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 × 10-4 to -1.4 × 10-3). Computational calculations were used to elucidate the changes in photophysical properties.
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