Amine-containing calixarenes for lanthanide coordination

INOR 304

Jordan L. Fantini, fantinij@denison.edu1, Samantha A. Williams, willia_sa@denison.edu1, Joseph A. R. Schmidt, Joseph.Schmidt@utoledo.edu2, and Matthew P. Hertel2. (1) Department of Chemistry and Biochemistry, Denison University, Ebaugh Laboratories, Granville, OH 43023, (2) Department of Chemistry, The University of Toledo, 2801 W. Bancroft St. MS 602, Toledo, OH 43606
Calixarenes are macrocyclic compounds commonly employed as multidentate ligands for transition metal and lanthanide ions. This study involves the synthesis of calix[4]arene compounds bearing a single amine-terminated group at the methylene bridge (2-position). Deprotonation of calixarene 1 with n-butyllithium yielded monolithiated intermediate 2. Treatment of 2 with a 1-bromo-ω-chloroalkane (chain length = 3 – 5) afforded a series of 2-(ω-chloroalkyl)calix[4]arenes (3a–c). Conversion of compounds 3 to analogous amine compounds 4a-c was carried out by reaction of 3 with excess amine, sodium or potassium carbonate, and potassium iodide in THF. Compound 4 was investigated as a ligand for yttrium and lanthanum by employing either protonolysis or salt metathesis routes. The metalated species of the form LMX2 (M = Y, La; X = halide, alkyl, amide) were characterized by various spectroscopic techniques. Further investigation of the reactivity of these compounds will be described.

 

Synthetic Coordination Chemistry
7:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Inorganic Chemistry

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