Design, synthesis and applications of NIR-emissive scaffolds of diketopyrrolopyrrole-aza-BODIPY hybrids

Herein, we report a facile synthetic method towards diketopyrrolopyrrole-aza-BODIPY hybrids by a two-step strategy. The three resulting fluorophores (LAB-TH4 LAB similar to TH6) showed absorption maxima up to 637 nm with molar extinction coefficients (epsilon) up to 32300 M-1 cm(-1) and emission maxima at 661 nm with a fluorescence quantum yield of 25.2% in solution. Due to good biocompatibility and strong ROS generation ability, they are useful fluorophores for bioimaging and photodynamic therapy (PDT). In addition, as a useful scaffold, a novel NIR-emissive conjugated polymer can be constructed by further bromination and Suzuki coupling polymerization.

Automated summary

A facile synthetic method was used to synthesize diketopyrrolopyrrole-aza-BODIPY hybrids. The resulting fluorophores showed high absorption and emission wavelengths in solution, as well as good biocompatibility and strong ROS generation ability, making them useful for bioimaging and photodynamic therapy. Furthermore, a novel NIR-emissive conjugated polymer can be constructed using this method.