Dithiane, Trithiane, and Dithiazane-Based Photolabile Scaffolds for Molecular Recognition: Mechanism and Efficiency of the Photoinduced Fragmentation in Aqueous Reductive Environments

Abstract

Photoinduced fragmentation in dithiane and trithiane adducts of aromatic ketones and aldehydes was studied in aqueous reductive environments. Density functional computations were carried out for thioxanthone derivatives bearing donor and acceptor substituents in the aromatic ring to identify the substitution pattern that is most promising for the productive irreversible electron transfer.

KeyWord:

• Mesolytic fragmentation
• photoinduced electron transfer
• sulfur-centered cation radicals
• thioxanthone

Acknowledgments

Support of this research by the National Science Foundation, Grant CHE-314344, is gratefully acknowledged.