Molecular recognition studies on supramolecular systems. 32. Molecular recognition of dyes by organoselenium-bridged bis(β-cyclodextrin)s

Y. Liu, B. Li, C. C. You, T. Wada, Y. Inoue

Research output: Contribution to journalArticle

70 Citations (Scopus)

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 I 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.

Original languageEnglish
Pages (from-to)225-232
Number of pages8
JournalJournal of Organic Chemistry
Volume66
Issue number1
DOIs
Publication statusPublished - 2001 Jan 12
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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