Modular and stereoselective synthesis of tetrasubstituted vinyl sulfides leading to a library of AIEgens

Xun-Shen Liu, Zhiqiong Tang, Zhiming Li (), Mingjia Li, Lin Xu and Lu Liu ()
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Xun-Shen Liu: East China Normal University
Zhiqiong Tang: East China Normal University
Zhiming Li: Fudan University
Mingjia Li: East China Normal University
Lin Xu: East China Normal University
Lu Liu: East China Normal University

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Tetraarylethylenes exhibit intriguing photophysical properties and sulfur atom frequently play a vital role in organic photoelectric materials and biologically active compounds. Tetrasubstituted vinyl sulfides, which include both sulfur atom and tetrasubstituted alkenes motifs, might be a suitable skeleton for the discovery of the new material molecules and drug with unique functions and properties. However, how to modular synthesis these kinds of compounds is still challenging. Herein, a chemo- and stereo-selective Rh(II)-catalyzed [1,4]-acyl rearrangements of α-diazo carbonyl compounds and thioesters has been developed, providing a modular strategy to a library of 63 tetrasubstituted vinyl sulfides. In this transformation, the yield is up to 95% and the turnover number is up to 3650. The mechanism of this reaction is investigated by combining experiments and density functional theory calculation. Moreover, the “aggregation-induced emission” effect of tetrasubstituted vinyl sulfides were also investigated, which might useful in functional material, biological imaging and chemicalnsing via structural modification.

Date: 2021
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DOI: 10.1038/s41467-021-27167-x

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