Molecular Recognition Studies on Supramolecular Systems. 32.1 Molecular Recognition of Dyes by Organoselenium-Bridged Bis(β-cyclodextrin)s

Publisher Website
Google Scholar
Abstract
A series of novel bis(β-cyclodextrin)s tethered with organoselenium linkers, i.e., 6,6‘-(o-phenylenediseleno)-bridged bis(β-cyclodextrin) (2), 6,6‘-[2,2‘-diselenobis(benzoyloxy)]-bridged bis(β-cyclodextrin) (3), and 6,6‘-[2,2‘-diselenobis[2-(benzoylamino)ethylamino]]-bridged bis(β-cyclodextrin) (4), were synthesized from β-cyclodextrin (1). The inclusion complexation behavior of 1−4 with some dyes, such as 8-anilinonaphthalenesulfonate (ANS), Brilliant Green, Crystal Violet, Tropaeolin OO, Auramine O, and Methyl Orange, was investigated in aqueous phosphate buffer solution (pH 7.20) at 25 °C by UV−vis, fluorescence, and circular dichroism spectrometry, as well as fluorescence lifetime measurements. The complex stability constants (KS) and Gibbs free energy changes (ΔG°) for the stoichiometric 1:1 inclusion complexation of 1−4 with the dyes were obtained by the spectrophotometric or spectropolarimetric titrations. The bis(β-cyclodextrin)s 2−4 showed much higher affinities toward these guest dyes than native β-cyclodextrin 1 with fairly good molecular selectivities. The cooperative binding abilities of these bis(β-cyclodextrin)s are discussed from the viewpoints of size/shape-fit interaction, induced-fit concept, and multiple recognition mechanism.

This publication has 33 references indexed in Scilit: