Synthesis of new generation Near-IR fluorescent squaraine-rotaxanes

ORGN 787

Na Fu, Easwaran Arunkumar, and Bradley D. Smith, smith.115@nd.edu. Department of Chemistry and Biochemistry, University of Notre Dame, South Bend, IN 46556
Squaraine dyes are susceptible to nucleophilic attack and self-quenching effects upon aggregation, which limits their application as Near-IR fluorophores. Both problems are eliminated by encapsulating the dye inside a macrocycle to form a squaraine-rotaxane. The macrocycle protects the electrophilic cyclobutene core of the squaraine thread from attack by nucleophile and also prevents interchromophore aggregation. At the same time, the rotaxanes keep the favorable photophysical properties of the precursor squaraines. We intend to employ these Near-IR dyes in bioimaging techniques and so we have evaluated the chemical and photophysical properties in biological environments. The presentation will include examples of these dyes as selective Near-IR stains for cells and tissues.

 

Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006