Investigation on inter molecular complexation between 4,4′-methylene-bis(N,N-dimethylaniline) and β-cyclodextrin: Preparation and characterization in aqueous medium and solid state

The purpose of this research was to investigate the inclusion complex formation between 4,4'-methylene-bis(N,N-dimethylaniline) (MBDA) and beta-cyclodextrin (beta-CD). The inclusion complex of MBDA and beta-CD was characterized both in solution and solid state by UV-Visible spectroscopy, fluorescence spectroscopy, Differential Scanning Calorimetry (DSC), Fourier Transform Infra-red spectroscopy (FT-IR), Scanning Electron Microscopy (SEM), Powder X-ray diffractometry (XRD) and Atomic Force Microscopy (AFM). The solid inclusion complex was prepared by co-precipitation method. The 1:1 stoichiometry of inclusion complex and binding constant were determined by Benesi-Hildebrand plot and was confirmed by Jobs continuous variation method. The spectral shifts revealed that only a part of MBDA molecule is entrapped in the beta-CD cavity. Nanosecond time resolved fluorescence study revealed that MBDA exhibits single exponential decay in aqueous medium and bi-exponential decay in beta-CD medium indicating the formation of 1:1 inclusion complex. The Gibbs free energy change of the complexation process was determined and it was found that the inclusion complexation process was spontaneous. The most probable structure of the inclusion complex of MBDA and beta-CD was proposed based on the molecular docking study. (C) 2014 Elsevier B.V. All rights reserved.