Synthesis, Reactivity, and Properties of a Class of π-Extended BODIPY Derivatives

A new family of pi-extended BODIPY derivatives were obtained through the condensation of aldehyde and pyrrole in aqueous solution in the presence of HCl. The new rigid pi-framework extends beyond the dipyrromethene unit, which is significantly different from classical BODIPYs in the electronic configuration. Both pi-extended BODIPYs displayed intense absorption and moderate emission with maxima around 565 and 620 nm, respectively, and showed interesting reactivity toward various nucleophiles. Moreover, these pi-extended BODIPYs were developed as fluorescent probes for rapid and selective detection of GSH and were successfully applied for live-cell imaging.

Automated summary

A new family of pi-extended BODIPY derivatives with unique structure and properties were synthesized, showing interesting reactivity towards various nucleophiles. These pi-extended BODIPYs can serve as fluorescent probes for rapid detection of GSH and live-cell imaging.