Functionalized calix[4]pyrroles: Synthesis and anion binding properties

ORGN 372

Jonathan L. Sessler1, Won-Seob Cho1, Bobbi Rubin1, Ginny A. Coddou1, Hee-Kyung Na2, Jin-Suk Lee2, Dae-Wi Yoon2, and Chang-Hee Lee2. (1) Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station - A5300, Austin, TX 7812-0165, (2) Chemistry, Kangwon National University, Chun-Chon, 200-701, South Korea
Calix[4]pyrrole (1) is one of the better-known neutral anion-binding agents. It has been extensively studied due to its attractive features, which include an exceptionally easy synthesis and anion binding characteristics that are potentially “tunable”. In effort to “tune” the anion binding properties of the calix[4]pyrroles, systems such as 3 that contain ether linkages, were synthesized. Such systems display greatly enhanced anion binding affinities and selectivities. However, as yet, the strap effect has not been studied systematically. Nor, have the effects of functionilization with various anion recognizing “tails”. In this poster, the synthesis of various mono-functionalized, urea-containing calix[4]pyrroles (e.g., 2), and strapped calix[4]pyrroles (3 and 4) is presented along with a discussion of their anion binding affinities and selectivities.

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