Synthesis and conformational control studies of new atropisomer platforms as molecular switches

ORGN 82

Judith M. Lavin, lavin@mail.chem.sc.edu, Department of Chemistry an Biochemistry, University of South Carolina, 631 Sumter Street, Columbia, SC 29208 and Ken D. Shimizu, Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter Street, Columbia, SC 29208.
Synthesis and Conformational Control Studies of New Atropisomer Platforms as Molecular Switches

The development of new molecular switches with the ability to adapt to the presence of a guest molecule and save the corresponding conformation is presented. The atropisomeric molecules exist in at least two conformations resulting from restricted rotation about a single bond within a rigid backbone. The high barrier of rotation of the atropisomers allows the individual conformational isomers to be saved at room temperature. These conformational preferences can be altered or erased, returning to an equilibrium mixture at elevated temperatures. The ability to interact selectively with guest molecules through hydrogen bond interactions is dependent on the isomer conformation. This report describes the synthesis of these switchable scaffolds, the ability to control the molecular conformation and the recognition capabilities of these new atropismer hosts.