Fluorescent chemosensors of toxic chloroalkanes

ORGN 261

Jung-Jae Lee, jlee7@nd.edu, Department of Chemistry & Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556-5670 and Bradley D. Smith, smith.115@nd.edu, Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556.
The naphthalene based macrocyclic amines, 1 and 2, exhibit photoinduced electron transfer (PET) and excimer fluorescence sensing of carcinogenic chloroalkanes, including the common industrial solvent methylene chloride. The macrocycles trap the chloroalkanes by undergoing a dramatically enhanced Menschutkin reaction. Mechanistic studies indicate that the reaction proceeds via a pre-reaction complex that activates the chloride leaving group. Macrocycle 1 exhibits a large increase in excimer emission due to non-covalent dimerization of the reaction product 3, whereas, the conversion of macrocycle 2 into product 4 leads to a 10-fold increase in monomer intensity due to diminished quenching by PET.

 

Molecular Recognition and Self Assembly
1:00 PM-4:40 PM, Monday, April 7, 2008 Morial Convention Center -- Rm. R04, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008