Nonsymmetric Benzo[]fused and Thiophene/Thieno[3,2-]thiophene[]fused BODIPYs: Synthesis and Photophysical Properties.

The fusion of sufficient-electron heterocycle rings into the[]/[]-position of the BODIPY core would result in a large redshift wavelength, thus achieving red or near infrared emission. In this paper, we described the synthesis of nonsymmetric benzo[]fused and thiophene/thieno[3,2-]thiophene[]fused BODIPY derivatives while containing a reactive site, and then, were developed by nucleophilic substitution reactions of with various nucleophilic agents in high yields. X-ray crystallographic analysis of revealed that the core structure adopted a planar geometry and π-π interactions were observed in the packing structure. BODIPYs and displayed a hypochromic shift in the absorption and bathochromic shift in the emission with increasing solvent polarity because of the formation of resonance structures resulting from the change of the C-N distance, which was rationalized by density functional theory (DFT)/time-dependent-DFT calculations.