Spectroscopic studies of inclusion complexation between ortho derivatives of p-methylaminobenzoate and α- and γ-cyclodextrins
Karolina Baranowska , Marek Józefowicz
AbstractUsing the steady-state and time-resolved spectroscopic techniques and quantum-chemical calculations, photophysical and photochemical properties of the two ortho derivatives of p-methylaminobenzoate (methyl o-methoxy p-methylaminobenzoate (I) and methyl o-hydroxy p-methylaminobenzoate (II)) have been studied in binary mixture THF-H2O and aqueous solutions containing different concentrations of α- and γ-CD. Nonlinear solvatochromic shifts of the absorption and fluorescence bands were observed for both fluorophores in a mixture of polar aprotic (THF) and polar protic (H2O) solvents. This nonlinearity has been explained in terms of the non-specific (dielectric enrichment of the solvent around the polar solute) and specific (hydrogen bond) solute-solvent interactions. Spectroscopic measurements were used to investigate the role of H-bonding solute-solvent interactions, and the excited-state intramolecular proton transfer process in the formation of inclusion complexes between fluorophore and cyclodextrins. The obtained results were used to calculate, according to Benesi–Hildebrand's plot and nonlinear least-squares regression analysis, equilibrium constants of the fluorophore-cyclodextrin inclusion complexes. Performed analysis indicates also that both 1:1 and 1:2 inclusion complexes were formed between studied compounds and α- and γ-cyclodextrins.
|Journal series||Journal of Molecular Liquids, ISSN 0167-7322, (A 30 pkt)|
|Publication size in sheets||0.5|
|Keywords in English||cyclodextrins, hydrogen bonding, excited-state intra molecular proton transfer, solute-solvent interactions|
|ASJC Classification||; ; ; ; ;|
|Score||= 30.0, 28-01-2020, ArticleFromJournal|
|Publication indicators||= 0; : 2018 = 1.275; : 2018 = 4.561 (2) - 2018=4.136 (5)|
|Citation count*||1 (2020-02-05)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.