Nanochain and vesicles formed by inclusion complexation of 4,4′-diaminobenzanilide with cyclodextrins

Abstract

The nanochain-like agglomerates and spherical nanovesicles were formed from supramolecular self-assembly of 4,4 0 -diaminonenzanilide (DABA) with a-and b-cyclodextrins. The DABA with a-CD and b-CD inclusion complex nanomaterials were prepared and characterised by transmission electron microscopy, scanning electron microscopy, FTIR, differential scanning calorimetry, 1 H NMR and powder X-ray diffraction. 1 H NMR analysis indicated that the benzamido ring of DABA was encapsulated into the cyclodextrin (CD) cavity. Absorption and fluorescence spectral studies suggested that DABA forms different types of nanomaterials in a-CD and b-CD solutions. Higher occupied molecular orbital, lower unoccupied molecular orbital, and thermodynamic parameter values confirmed DABA dye entrapped in the CD cavities.

Photophysics of Caffeic, Ferulic and Sinapic Acids with α- and β-Cyclodextrins: Spectral and Molecular Modeling Studies

“…72 The above results showed that, the guest molecules were transferred from more protic environments (bulk aqueous phase) to less protic CD cavity environments [1][2][3][4][5][6][7][8][9][10][26][27][28][29][30][31]. Similar spectral shifts of all the HCAs showed that same type of the functional group is encapsulated and this functional group is interacted with the secondary hydroxyl groups of the CD.…”

“…It should be noted that such a comparison is significant because of the small shift in the fluorescence and absorption spectra. A similar characteristic is also observed in various guests by various authors [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. Considering the length of HCA molecules and the CD cavities, one can expect two types of inclusion complex may be formed.…”

“…In our earlier communications, we reported the dual emission characteristics of many drugs and dyes [1][2][3][4][5][6][7] found that ICT and hydrogen bonding plays an important role in polar solvents and CD. The drug and dye molecules interestingly forms inclusion complex with cyclodextrin having a preferential orientation of the OH/methoxy group sticking outside in aqueous solvent and just the reverse is the case in nonaqueous solvent.…”

“…The interesting and exciting phenomenon of intramolecular charge transfer (ICT) in many drugs and dyes [1][2][3][4][5][6][7][8][9][10] has engendered a deep concentration in studying its photophysical properties in hydrophobic cavities of cyclodextrins. The dependence of ICT emission on environmental polarity, viscosity as well as rotational mobility of donor moiety makes these drugs and dyes molecules outstanding candidates [10][11][12][13][14][15][16][17][18] for examining microscopic molecular environments.…”

Photophysics of Caffeic, Ferulic and Sinapic Acids with α- and β-Cyclodextrins: Spectral and Molecular Modeling Studies

“…Cyclodextrins (CD) are cyclic oligosaccharides that form hydrophobic and restrictive cavities with hydrophilic external walls in aqueous solution, given those attractive dissimilar microenvironments with a capability to include guest molecules. The interesting and exciting phenomenon of intramolecular charge transfer (ICT) in many drugs and dyes [1][2][3][4][5][6][7][8][9][10] has engendered a deep concentration in studying its photophysical properties in hydrophobic cavities of cyclodextrins. The dependence of ICT emission on environmental polarity, viscosity as well as rotational mobility of donor moiety makes these drugs and dyes molecules outstanding candidates [10][11][12][13][14][15][16][17][18] for examining microscopic molecular environments.…”