Thiophosphorylated cavitand: structure and affinity towards soft metal ions

The iiii stereoisomer of the tetrathiophosphonate-calix[4]resorcinarene host 1 exhibited excellent extraction properties towards soft metal ions, with a better affinity for Ag+ (91%), than for Tl+ (38%) and Hg2+ (16%). The extraction of other picrate salts (Cu2+, Ni2+, Co2+, Zn2+, Cd2+, Pb2+) was not detected. The stoichiometry and the structure of the Hg2+, Tl+ and Ag+ complexes were studied by NMR in solution and gave respectively 1:1, 1:1 and 1:2 host-guest complexes. The formation of the self-assembled 1(2).(AgPic)(4) complex was independent on the anion and only observed with silver(l) ion. (C) 2003 Elsevier Ltd. All rights reserved.