Replacing the BO in BODIPY: unlocking the path to SBDIPY and BIDIPY chromophores

Abstract

Boron-based dipyrrin chromophores (BODIPY) have found widespread application over the last twenty years in fields as diverse as medicine and materials. Thus, several efforts have been placed to exchange boron with other elements, with the aim of developing materials with complementary luminescent properties. However, despite these attempts, the incorporation of other main-group elements in dipyrrin scaffolds remains still rare. We have successfully synthesized and characterized novel chromophores based on antimony and bismuth, SBDIPY and BIDIPY. Solution stabilities have been investigated by VT-UV/vis spectroscopy and the fluorescence emission studied and supported by computational analysis. We were also able to isolate the first direct analogue of BODIPY containing fluoride handles, disclosing preliminary luminescent features.