119 Synthesis of Novel Di-Ionizable Calixarene Ligands in the Cone, 1,3-Alternate and Partial Cone Conformations

Wednesday, November 4, 2009: 11:00 AM
Rio Grande (Camino Real Hotel)
Pillhun Son , Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX
Eun Kyung Lee , Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX
Louisa J. Hope-Weeks , Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX
Richard A. Bartsch , Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX

Novel di-ionizable calix[4]arene ligands have been synthesized in the cone (1), 1,3-alternate (2) and partial cone (3 and 4) conformations as potential extractants for metal cations. A crucial point in the synthesis steps was control of the conformation during each alkylation step, which was achieved by variations in the base, solvent, addition method and other reaction conditions. Four different conformations were obtained for dibromo-tetrabutoxycalix[4]arenes and verified by 1H and 13C NMR spectroscopy. Also a solid-state structure was obtained for one compound. Two types of partial cone conformations were achieved, namely anti upper rim-functionalized partial cone 3 and syn upper rim-functionalized partial cone 4. Solvent extractions of the metal ions were performed with the cone and 1,3-alternate series for alkali metal and alkaline earth metal cations, as well as for Pb2+  and Hg2+.

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