New pyrrole- and (thio)urea-based tripodal anion receptors

ORGN 612

Grigory Zyryanov, zgrigor@bgnet.bgsu.edu and Pavel Anzenbacher Jr., pavel@bgsu.edu. Department of Chemistry and Center for Photochemical Sciences, Bowling Green State University, Overman Hall 141, Bowling Green, OH 43403
Anion binding by receptors and sensors utilizing hydrogen bonding to establish the anion-receptor complex requires precise spatial arrangement of hydrogen bond donors. The 1,3,5-triaminomethyl-2,4,6-triethylbenzene scaffold, the so-called Anslyn's amine, offers an opportunity to form C3-symmetrical receptors, which appear to be ideally preorganized to bind either spherical anions, phosphate, nitrate as well as carboxylates. In our presentation, we will discuss the synthesis and anion-binding properties of various receptors and sensors utilizing 1,3,5-triaminomethyl-2,4,6-triethylbenzene bearing varying combinations of convergent hydrogen-bonding units, namely amide, urea, and thiourea moieties. The anion binding properties of these receptors were studied by proton NMR. Also, the attachment of fluorescent labels allowed observing the corresponding binding process by optical methods such as absorption and fluorescence spectroscopy. This presentation will discuss the results of the anion sensing experiments in solution and polymer matrices, and the potential application of these sensors in arrays.
 

Molecular Recognition and Self-Assembly
1:00 PM-5:00 PM, Wednesday, March 28, 2007 McCormick Place Lakeside -- Room E352, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007