Synthesis and Applications of Seleno- and Telluro-BODIPY Derivatives: Near Infrared Fluorescent Sensors

Abstract

The present project aims towards the preparation of new chalcogen-containing near infrared (NIR) fluorescent BODIPY derivatives. The BODIPY and aza-BODIPY nuclei will be explored in this investigation. The derivatization of the BODIPY cores will rely on the insertion of heteroaromatic chalcogen moieties that are conjugated to the chromophoric core in order to achieve significant bathochromic shifts on the absorption/emission maxima (steric effect and heavy atom effect). In addition, the BODIPY derivatives will also contain chalcogen atoms (Se and Te) connected to the chromophoric nuclei aiming fluorescense supression by reductive photoinduced electron transfer (d-PeT). By oxidation of the Se or Te atoms to the corresponding chalcogenoxides/chalcogenones, the fluorescence will be reestablished and this phenomenon will allow the use of these chromophores as on/off-sensors capable of detecting endogenous reactive oxygen and nitrogen species (ROS, RNS) in vivo and also, other environmentally important analytes. (AU)