Synthesis and aggregation properties of boron-dipyrromethene dyes conjugated with guanine units

Abstract

Two boron-dipyrromethene dyes bearing a conjugated guanine unit (G-BODIPYs) 1 and 2 were synthesized and fully characterized. The self-assembly properties of these dyes were investigated by X-ray crystallography, [Formula: see text]H NMR and UV-vis spectroscopy. As revealed by X-ray crystal structure studies, G-BODIPY 1 self-assembled into ribbon-like structures due to the intermolecular hydrogen bonding and [Formula: see text]–[Formula: see text] stacking interaction. Concentration-dependent [Formula: see text]H NMR experiments confirmed the formation of hydrogen bonds of the guanine units in solution for both dye 1 and 2. In the presence of K[Formula: see text], the characteristic signals for the formation of cyclic G-quadruplex structures were observed in the [Formula: see text]H NMR study. Aggregation of G-BODIPY dyes was further monitored by UV-vis absorption spectroscopy by varying the solvent polarity and temperature. H-type aggregates of dye 1, which was characterized by a new hypsochromically shifted absorption band with [Formula: see text] 461 nm, was obtained. In the presence of K[Formula: see text], the enhancement of stability was observed for the H-aggregates of dye 1.