Four beta-cyclodextrin (beta-CD) derivatives bearing pyridine or bipyridine linkers, i.e., mono [6-(3-pyridinecarboxamide)ethyleneamino-6-deoxy]-beta-CD (2), mono [6-(4-pyridinecarboxamide)ethyleneamino-6-deoxy]-beta-CD (3), N,N'-bis(2-aminoethyl)-2,2'-bipyridine-4,4'-dicarboxamide-bridged bis(6-amino-6-deoxy-beta-CD) (4), N,N'-bis(2-aminoethyl)-2,2'-bipyridine-3,3'-dicarboxamidede-bridged bis(6-amino-6-deoxy-beta-CD) (5), and their copper(II) complexes (6 and 7) were selected as molecular receptors to explore the conformation-function relationship of oligo( beta-CD)s. The original conformations of hosts 4-7 and their inclusion complexation behaviors with some guest molecules, i.e., ammonium 8-anilino-1-naphthalenesulfonate (ANS), sodium 6-(p-toludino)-2-naphthalenesulfonate (TNS), and rhodamine B (RhB), were comprehensively investigated by means of UV-vis, 2D NMR, and fluorescence spectroscopy. The results indicated that these oligo(beta-CD)s, especially bis(beta-CD) 5 and its copper(II) complex 7, exhibited the significantly enhanced binding abilities toward guest molecules as compared with native beta-CD. Typically, hosts 5 and 7 efficiently enhanced the original binding ability of native beta-CD toward ANS by a factor of 38-42 times. These increased binding abilities of oligomeric hosts were discussed from the viewpoint of the size/shape-fit and multipoint recognition between host and guest.