Abstract
Two series of novel mono-ionizable calix[4]arene-benzocrown-6 ligands in 1,3-alternate conformations are synthesized. In one series, the proton-ionizable group (PIG) is attached to the para position of one aromatic ring in the calixarene framework, thereby positioning it over the polyether ring cavity. In the other series, the PIG is a substituent on the benzo group in the polyether ring. This orients the PIG away from the crown ether cavity. In addition to carboxylic acid functions, the PIGs include N-(X)sulfonyl carboxamide groups. With X group variation from methyl to phenyl to 4-nitrophenyl to trifluoromethyl, the acidity of the PIG is 'tuned'. Solvent extraction of Ag+ from aqueous solutions into chloroform is used to probe the influence of structural variation within the mono-ionizable calixcrown ligand on metal ion extraction efficiency, including the identity and acidity of the PIG and its orientation with respect to the polyether ring.
| Original language | English |
|---|---|
| Pages (from-to) | 7777-7783 |
| Number of pages | 7 |
| Journal | Tetrahedron |
| Volume | 65 |
| Issue number | 37 |
| DOIs | |
| State | Published - Sep 12 2009 |
Funding
This research was supported at TTU by the Office of Biological and Environmental Research of the U.S. Department of Energy (Grant Number FG02-03ER63676). This research was supported at ORNL by the Environmental Management Science Program of the Offices of Science and Environmental Management of the U.S. Department of Energy (Contract Number DE-AC05-00OR22725).