Pillar[5]-bis-crowns with different donor sets in the crown unit (L¹: SNS and L²: SSS) have been synthesized and their three metallosupramolecules (1-3) have been obtained. First, the assembly reactions of L¹ with silver(I) salts having different anions afforded two disilver(I) complexes [Ag₂(L¹)(ClO₄)₂]•2CH₂Cl₂ (1: perchlorate form) and [Ag₂(L¹)(CH₃OH)₂](PF₆)₂•2CH₂Cl (1: hexafluorophosphate form). In both complexes, Ag(I) center is four-coordinated by the SNS donor set in the crown unit. The observed methanol coordination to the Ag(I) center in 2 gave us an inspiration to employ some bridging ligands to replace two individual methanol molecules which bind to each metal centers. As candidates for the bridging ligands for the linking of two Ag(I) centers, dialcohols (OH-(CH₂)_n-OH), dinitriles (CN-(CH₂)_n-CN), and dicarboxylates (^-OOC-(CH₂)_n-COO^-) are expected to show a length-selective recognition behavior depending on the values of n (1, 2, or 3..). These results might be a chemical example of the adaptive guest binding which observed in biology. Next, L² reacts with HgBr₂ to give a 1-D coordination polymer [Hg₆Br₁₂(CH₃CN@L²)₂]_n (3) in which two L² ligands up and down are linked by a linear Hg₃Br₆ unit to form a C-type dimer and the adjacent dimers are further linked by Hg-S bonds, giving rise a unique 1-D ribbon type structure with a poly(dimer) connectivity pattern.