Excimer emission of caffeine with α- and β-cyclodextrins: spectral and molecular modelling studies

ABSTRACTExcimer emission of caffeine with α-CD and β-CD were studied by UV-visible, fluorescence, time-resolved fluorescence, FTIR, 1H NMR and molecular modelling techniques. Changes in the absorbance and fluorescence and lifetime of the caffeine with cyclodextrin (CD) solutions indicate (i) caffeine shows dual emission in the CD solutions, (ii) normal emission originates from a monomer and the longer wavelength emission is due to excimer and (iii) in both CDs caffeine forms 1:2 inclusion complex. Carbonyl stretching frequency moved to higher wave numbers and broadening of the N–H stretching band indicated the formation of inclusion complex. The resonance of the methyl protons of caffeine show remarkable upfield or downfield shift in the 1H NMR, which indicates imidazole ring of the caffeine entrapped in the CD cavities. Investigations of energetic, thermodynamic and electronic properties of PM3 computational calculations confirmed the stability of the inclusion complex.