Formation of rhodamine B spirolactams for the development of selective sensing materials

ORGN 480

Clifton J. Stephenson, stephenson@mail.chem.sc.edu1, Kevin M. Yehl, yehlk@mailbox.sc.edu2, and Ken D. Shimizu, shimizu@mail.chem.sc.edu2. (1) Department of Chemistry & Biochemistry, University of South Carolina, 631 Sumter St., Columbia, SC 29208, (2) Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter St., Columbia, SC 29033
The xanthene dye rhodamine B (RB) can exist in two forms: open and closed. The closed form is typically colorless and non-fluorescent. The open form is colored (ranging from pink to red) and fluorescent. Rhodamine dyes can be switched from the closed to open form by changing the pH or polarity of the solution. Recent work demonstrated the unique sensing potential of an on/off RB system for the differentiation of diastereomeric amino alcohols and as a tool to determine diastereomeric excess. This sensing potential has led to the development of an amide form of RB that affords a straightforward modification point for the addition of a wide range of substrates that produces molecular recognition based sensors for different classes of small bio-relevant molecules. Herein is an account of the development of RB lactams derivates and the analysis of their differentiating potential.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007