Facile Synthesis of Sulfur-Containing Functionalized Disiloxanes with Nonconventional Fluorescence by Thiol-Epoxy Click Reaction

Herein, a series of novel sulfur-containing functionalized disiloxanes based on a low-cost and commercially available material, i.e., 1,3-bis(3-glycidoxypropyl)-1,1,3,3-tetramethyldisiloxane, and various thiol compounds were prepared by thiol-epoxy click reaction. It was found that both lithium hydroxide (LiOH) and tetrabutylammonium fluoride (TBAF) have high catalytic activity after optimizing the reaction condition, and the reaction can be carried out with high yields, excellent regioselectivity, mild reaction condition, and good tolerance of functional groups. These compounds exhibit excellent nonconventional fluorescence due to the formation of coordination bonds between Si atoms and heteroatoms (e.g., S or N) and can emit blue fluorescence upon ultraviolet (UV) irradiation. These results demonstrate that the thiol-epoxy click reaction could promisingly act as an efficient organosilicon synthetic methodology to construct various organosilicon materials with novel structures and functionality, and thus their application scope will be significantly expanded.

Automated summary

A series of novel sulfur-containing functionalized disiloxanes were prepared by thiol-epoxy click reaction using 1,3-bis(3-glycidoxypropyl)-1,1,3,3-tetramethyldisiloxane and various thiol compounds. The reaction conditions were optimized, and both lithium hydroxide and tetrabutylammonium fluoride showed high catalytic activity, resulting in high yields, excellent regioselectivity, mild reaction conditions, and good tolerance of functional groups. These compounds exhibited unique fluorescence properties due to the formation of coordination bonds between Si atoms and heteroatoms (S or N), emitting blue fluorescence under UV irradiation. The thiol-epoxy click reaction is a promising synthetic methodology for constructing various organosilicon materials with novel structures and functionality.