Supramolecularly Assisted Modulation of Optical Properties of BODIPY–Benzimidazole Conjugates

Abstract

Supramolecular host-guest interaction of neutral and cationic (protonated) forms of two boron-dipyromethane (BODIPY)-benzimidazole (mono- and di-benzimidazole) conjugate dyes with the macrocyclic host cucurbit[7]uril (CB7) has been investigated using photophysical and density functional theory studies. Expectedly, cationic forms of the dyes show exceptionally stronger binding than that of the neutral forms with CB7, which can be ascribed to the strong ion-dipole interaction between the positive charge of the dye and the highly polarizable carbonyl portals of the host. The formation of dye-host inclusion complexes is supported by the significant changes in the photophysical properties and longer rotational relaxation times of the dye in the presence of CB7. Job's plot studies indicate the formation of a 1:1 inclusion complex for the mono and a 1:2 inclusion complex for the dibenzimidazole BODIPY dyes. Quantum chemical calculations are in good agreement with the inferences outlined from photophysical measurements. Findings from the studied dye-CB7 systems are of direct relevance to applications such as drug delivery, aqueous dye lasers, sensors, and so on.