Study on preparation and inclusion behavior of inclusion complexes between β-cyclodextrin derivatives with benzophenone

Abstract

In the paper, the two chemically modified β-cyclodextrin derivatives of 4,4´-diaminodiphenyl ether-bridged-bis-β-cyclodextrins (ODA-bis-β-CD) and p-aminobenzenesulfonic acid-β-cyclodextrin (ABS-β-CD) were synthesized, and then these two β-cyclodextrin derivatives were respectively formed into inclusion complexes with benzophenone (BP) by co-precipitation method. The structure of the inclusion complexes were characterized by UV/vis spectroscopy, FT-IR spectroscopy, elemental analysis, 1H NMR spectroscopy and XRD. Spectral titration was performed to study the inclusion behavior of the inclusion complexes. These experiments indicated that two inclusion complexes were formed at a stoichiometric ratio of 1:1 and the inclusion stability constants at different temperatures were calculated using the Benesi–Hildebrand (B–H) equation. The thermodynamic parameters (ΔG°, ΔH°, ΔS°) were obtained. As a result, it was found that the two chemically modified β-cyclodextrins containing BP were exothermic and spontaneous process (ΔG° < 0), and the processes of inclusion complexation were mainly enthalpy driven with negative or minor negative entropic contribution.