Efficient light absorbers based on thiophene-fused boron dipyrromethene (BODIPY) dyes

We present the development of the thiophene-fused boron dipyrromethene derivatives as efficient light absorbers. The two strategies for the evolution of the optical properties such as the peak positions of absorption wavelengths and molar extinct coefficients were established by the substituent effects: by introducing iodine groups, the bathochromic shifts of the peak positions (+15 nm) and the enhancement of molar extinct coefficients were simultaneously received owing to the heavy atom effect. Next, it was found that the modification with the trifluoromethyl group contributed to the large bathochromic shift (+60 nm) because of the lowering effect on the lowest unoccupied molecular orbital of the dye by the substituent. Finally, we obtained the dyes with large molar extinct coefficients (184,140 M-1 cm(-1) at 592 nm, 72,180 M-1 cm(-1) at 623 nm), sharp absorption bands, and low emissions. (C) 2013 Elsevier Ltd. All rights reserved.