A series of π-expanded coplanar BODIPY dyes with deep-red emission: Synthesis, optical properties, and application in amplified spontaneous emission

Boron dipyrromethene (BODIPY)-derived dyes are a class of superior emitters, and a classic BODIPY structure has absorption and emission at similar to 500 nm. To meet the practical application requirements, this work was dedicated to the design and synthesis of BODIPY emitters covering the deep-red region with a high emission quantum yield. Aromatic rings and a well-known electron-withdrawing group, -CF3, were introduced into a pi-expanded BODIPY structure. These BODIPY emitters were discussed in detail, including their thermal stability and optical parameters, as well as their photodynamic therapy performance. The correlation between the BODIPY photophysical performance and their substituents was discussed. It was found that the formation of a pi-expanded coplanar conjugation chain successfully shifted BODIPY emission to the deep-red region (626 nm) with a high quantum yield (0.99). The -CF3 modification on the BODIPY meso-C, however, quenched its emission. A threshold energy for the ASE (amplified spontaneous emission) effect of 980 mu J was exhibited with an efficiency of 5.5%. The cell viability was decreased to 9.0 +/- 4.6% using these BODIPY dyes as a photosensitizer.

Automated summary

This work focused on the design and synthesis of deep-red emitting BODIPY dyes with high emission quantum yields. Introducing aromatic rings and the electron-withdrawing group -CF3 into the BODIPY structure successfully shifted the emission wavelength to 626 nm in the deep-red region with a high quantum yield of 0.99. However, modifying the meso-C of BODIPY with CF3 quenched its emission.