Effect of Oxidation on the Chiroptical Properties of Sulfur-Bridged Binaphthyl Dimers

J Org Chem. 2022 Sep 16;87(18):12315-12322. doi: 10.1021/acs.joc.2c01516. Epub 2022 Sep 6.

Abstract

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.