Synthesis and characterization of red to near-infrared chiral boron-stereogenic α-alkenyl BODIPYs

Chiral BODIPYs have attracted increasing interest due to their remarkable photophysical properties and flexible modification towards structural diversity. Nevertheless, most of the current strategies focus on constructing chiral BODIPYs with defined absorption and emission ranging from 500-600 nm, which might limit their applications as chiral fluorophores. Herein, we described a straightforward strategy by installing alkenyl groups at the alpha-position of pre-chiral BODIPYs to construct three kinds of boron-stereogenic BODIPYs in moderate yields. The achieved boron-stereogenic BODIPYs showed promising photophysical properties, such as long-wavelength absorption (603 nm) and emission (710 nm), excellent fluorescence quantum yields, and mirror images as well as Cotton effects in circular dichroism and circularly polarized luminescence spectroscopies. This strategy provided a practical approach to access chiral BODIPYs.