A series of six calix[4]arene derivatives bearing allyl groups and/or benzy
l groups functionalized at the phenolic oxygen atoms were synthesized and t
heir cation-binding abilities for silver(I) and thallium(I) ions were evalu
ated through solvent extraction experiments. The results showed that both s
ilver(I) and thallium(I) picrates were readily extracted by the tetrasubsti
tuted p-t-butylcalixarene derivatives, while no extraction of sodium or pot
assium picrates was observed. The high extractability of thallium(I) picrat
e by these ligands was independent of the functional groups present, but th
e extraction of silver picrate seemed to be dependent on the conformational
rigidity of the calixarene; those locked into the cone conformation showed
the highest extractability for silver picrate.