Eletrocalcogenação de BODIPYs: eficiente uso de eletrossíntese na construção de sondas fluorescentes e sua aplicação em estudos de bioimageamento

Abstract

The present work describes the development of a synthesis method using electrochemistry for the functionalization of BODIPY (borondipyrromethanes) with organoselenium groups. The process used an undivided cell with platinum and reticulated vitreos carbon (RVC) electrodes, with diphenyl disselenide as the selenium source for the selenation of positions 2 and 6 of the BODIPY derivatives. The methodology employed here resulted in the synthesis of 20 novel compounds (90, 92-110) with yields between 25-77 %. The photophysics properties of these compounds was studied and compared with their respective starting materials. Three pairs of these compounds (13 and 90; 78 and 93; 79 and 94) were used in the process of obtaining bioimages of lipid droplets, and their data were compared with the precursors used. The present methodology presented allowed to obtain dyes with fluorescence in the red region, with potential use in organic tissue, such as adipose connective tissue. This class of compounds may provide a greater knowledge about the phenomena of fat accumulation, becoming a tool to combat diseases such as obesity and hepatic steatosis.