Aqueous Micellar-Catalyzed Thioetherification for the Synthesis of Aggregation-Induced Emission Molecules.

Abstract

1,1-Diphenylvinyl sulfide (DPVS) exhibits aggregation-induced emission (AIE) behavior by restricting intramolecular motion, making it a valuable aggregation-induced luminescent material. However, the synthesis of such AIE molecules typically involves organic sulfur reagents and toxic organic solvents, which limits their development in green synthesis conditions. In this study, we present a method for the multicomponent cross-coupling synthesis of DPVS in aqueous micellar conditions, utilizing iodine-mediated inorganic sulfur sources, such as elemental sulfur. The broad applicability of this method is demonstrated by the high-yield synthesis of over 20 different DPVS compounds using various inorganic sulfur sources. Furthermore, the glycosylated nonionic surfactant GluM can modify the coordination complexes formed by copper salts and ligands, significantly enhancing the solubility of substrates. Notably, when emulsions are used as detection reagents, the accuracy of detecting nitroaromatic explosives improves significantly, with a quenching constant of 92.28 × 10⁷. This advancement facilitates the application of AIE molecules in chemical sensing.