Rigid chiral tripodal ligands as chiroptical metal sensors: strategies to improve selectivity and efficiency

ORGN 566

Zhaohua Dai, Deapartment of Chemistry, New York University, 100 Washington Squre East, Rm 1001, New York, NY 10003, Nina Berova, Department of Chemistry, Columbia University, Havemeyer Hall, MC 3114, 3000 Broadway, New York, NY 10027, and James W. Canary, Department of Chemistry, New York University, New York, NY 10003, 29 Washington Place, New York, NY 10003.

Our interest in engineering improved selectivity toward zinc ion over copper(II) of some tripodal ligands through the incorporation of a chiral bias has been extended to rigid systems containing piperidine and quinuclidine rings.  The new piperidine and quinuclidine systems possess additional chiral centers and display interesting fluorescence and circular dichroism properties.  Structural information shows that stereochemistry is used to preorganize the receptors to achieve metal ion selectivity. High efficiency in zinc sensing can also be achieved from a chiroptical method utilizing fluorescence detection in circular dichroism (FDCD).

 


                   


 

Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003