Photolabile Amphiphiles with Fluorogenic Thioxanthone-Dithiane Functionality: Synthesis and Photoinduced Fragmentation in Micelles.

ABSTRACT: Novel photolabile amphiphiles containing thioxanthone-based fluorogenic caging groups are developed. Photoinduced fragmentation in dithiane-thioxanthone adducts was demonstrated to occur with 100% quantum efficiency at λ ~ 320 nm and more than 50% at λ ~ 360 nm. A plausible mechanism involves homolytic fission of a carbon-carbon single bond in the excited thioxanthone followed by disproportionation via hydrogen transfer. The critical feature of the system is that fluorescence of a substituted thioxanthone is recovered as a result of photofragmentation, making dithiane-thioxanthone adducts efficient fluorogenic caging groups. Photolabile amphiphiles containing these fluorogens are synthesized and their photoinduced disassembly is probed while following the fluorescence recovery. This method

SUBMITTER: Ezhov RN 

PROVIDER: S-EPMC3891307 | biostudies-literature | 2008

REPOSITORIES: biostudies-literature