Investigating lipophilicity of boron dipyrromethenes using experimental and computational approaches

Abstract

BODIPY fluorescent dyes is a versatile class of molecules with a wide spectrum of applications, particularly in biological imaging and sensing. For these applications, lipophilicity is a critical factor that influences the compound's solubility, biodistribution, and biological interactions. This study investigated the synthesis and lipophilicity characterization of a series of BODIPY fluorescent dyes. The lipophilicity of the compounds was determined by high-performance liquid chromatography and compared to the predictions of theoretical methods. The results demonstrated the effectiveness of some fragment-based methods in BODIPY's lipophilicity calculation. The role of hydrophobic surface area in molecular lipophilicity was also investigated. The findings of this study provide insights into the structure-property relationships of BODIPY dyes and can be used to design derivatives with desired lipophilicity for specific applications.