Synthesis of red-shifted meso-CF3-BODIPYs

Utilizing PhSiCl3, one-pot synthesis of meso-CF3-BODIPYs are achieved from the condensation of the pyrroles with CF3COOH for the first time. Herein PhSiCl3 acts as a vital role to provide the source of Cl for generating acyl chloride. Based on X-ray crystallographic analysis, the core skeleton of meso-CF3-BODIPY becomes non-planar and tortuous due to the introduction of the -CF3 group. Introduction of the -CF3 group into BODIPY resulted in a remarkably bathochromic shift to the NIR region. Meso-CF3-BODIPY with the dimethylamino groups is a turn-on fluorescent probe for pH. Singlet oxygen generation of dibromo substituted meso-CF3-BODIPY was found to be more effective and had about 2.4-fold rate enhancement compared to that of the parent meso-CF3-BODIPY.