Chiral atropisomeric xanthene dyes as chiral fluorescent sensors

ORGN 572

Kevin M. Yehl, yehlk@mailbox.sc.edu1, Clifton J. Stephenson, stephenson@mail.chem.sc.edu2, and Ken D. Shimizu, shimizu@mail.chem.sc.edu1. (1) Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter St., Columbia, SC 29033, (2) Department of Chemistry & Biochemistry, University of South Carolina, 631 Sumter St., Columbia, SC 29208
Xanthene dyes display restricted rotation about the central C(xan) -C(ary) single bond highlighted below. It is this property that will be focused on to synthesize axially chiral rhodamine and fluorescein molecules for the purpose of producing enantioselective sensing platforms. Such axial chirality is introduced to these xanthene fluorophores through desymmetrization via a Mannich reaction. The overall goal is to chirally functionalize rhodamine and fluorescein and to enantiomerically resolve the isomers in hopes of designing a new enantioselective sensing system.