Effects of organised media on the excited-state proton transfer in 2-(2'-pyridyl)benzimidazole

Abstract

Absorption and fluorescence characteristics of 2-(2'-pyridyl)benzimidazole (2-PBI) are studied in the presence of α- and β-cyclodextrins (CD) in aqueous solution at two different pHs. Steady-state and time-resolved fluorescence measurements are used for the investigation of the effect of organised media on the excited-state proton transfer reaction in 2-PBI. Semi-empirical CI calculation for the geometry of the molecule reveals that the 2-PBI molecule may be involved in host–guest complex formation with α-CD and β-CD in different configurations. NMR measurements corroborate this, providing information about the orientation of the 2-PBI molecule inside the cavity of the CDs. No complex formation was evident in γ-CD owing to its larger cavity dimension compared to the size of the 2-PBI molecule.