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The ability of tetra(p-t-butyl)tetrathiacalix[4]arenetetrol (TCA, H4L), a cyclic tetramer of p-(t-butyl)phenol bridged with four epithio groups, to bind metal ions was investigated via a solvent extraction study. Although tetra(p-t-butyl)calix[4]arenetetrol (CA) has very poor affinity for transition metal ions (M2+), TCA is an excellent extractant of these metal ions. The chemical formulae of the extracted TCA metal complexes were found by slope analysis to be neutral 1 : 1 complexes [MH2L]. The origin of the high affinity of TCA for transition metal ions is discussed, in which it is suggested that ligation of the epithio group is important as evidenced by an NMR study of the [ZnH2L] complex.

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p-tert- Butylcalix[4]arene-1,3-dithiol (BCAD) was synthesized to prepare a functionalized surface for host-guest molecular recognition by immobilizing it on the Au(100)-(1 × 1) surface in 0.05 M HClO4. In situ scanning tunneling microscopy (STM) was employed to investigate the structure of the adlayer of BCAD formed on the Au(100)-(1 × 1) surface. Highly ordered adlayers of BCAD with two different packing arrangements were found to form on the Au(100)-(1 × 1) surface. High-resolution STM images revealed the packing arrangement and even the internal molecular structure of BCAD.