Squaraine-rotaxanes: A new class of highly stable near-IR fluorescent dyes

ORGN 657

Arunkumar Easwaran, earun@rediffmail.com, Na Fu, and Bradley D Smith. Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556
A squaraine dye with bulky end groups is employed as the thread component in two Leigh-type amide rotaxanes. The rotaxanes are synthesized in a simple two step process. X-ray crystal structures of the rotaxanes show that the pyridyl-containing macrocycle is more rigid and wraps more tightly around the cyclobutene core of the squaraine thread compared to the isophthalamide-containing macrocycle. The rotaxanes exhibit photophysical properties that are similar to the precursor squaraine. The encapsulating macrocycle greatly increases the chemical stability of the squaraine thread, and inhibits aggregation-induced broadening of its absorption spectrum. It should be possible to prepare squaraine derived rotaxanes with improved properties for a wide range of photophysical, photochemical and biomedical applications.

 

Materials, Devices, and Switches
1:00 PM-5:00 PM, Thursday, 30 March 2006 Georgia World Congress Center -- Georgia Ballroom 2, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006