Pyrazine analogues of dipyrrolylquinoxalines: Synthesis, anion binding properties and incorporation in macrocycles

ORGN 565

G. Dan Pantos1, Jonathan L. Sessler1, Evgeny Katayev2, and Vincent Lynch1. (1) Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712-1167, (2) Department of Chemistry, Moscow State University, Vorob'yovy gory, Moscow, 119899, Russia

The design of anion receptors is a prominent research area in the field of supramolecular chemistry. Dipyrrolylquinoxalines represent one of several anion receptors designed in our group. In this poster we report the synthesis and binding properties of a new class of pyrazine-oligopyrrole class of anion receptors. The ability of these motifs (1 - 4) to bind biologically relevant anions such as chloride, dihydrogen phosphate, and di- and monocarboxylates was investigated using UV-Vis and 1H-NMR spectroscopic titrations. The incorporation of parent compound 1 into a phthalocyanine scaffold will also be presented. Such new directions could open the door towards the development of novel noncovalent supramolecular scaffolds.

Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses 11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster Division of Organic Chemistry The 226th ACS National Meeting, New York, NY, September 7-11, 2003