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Direct seleno- and telluro-functionalization of positions 3 and 5 from the BODIPY core via radical approach

Grant number: 20/04782-7
Support type:Scholarships in Brazil - Master
Effective date (Start): August 01, 2020
Effective date (End): February 28, 2022
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Alcindo Aparecido dos Santos
Grantee:João Luiz Petrarca de Albuquerque
Home Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

Over the past few decades there has been a increasing interest on the synthesis of fluorescent compounds and their usage as fluorescent probes to detect inorganic analites, such as metal cations, or to detect biomolecules, specially at in vivo assays. Among the most used probes prevail the dipyrromethene derivatives, notably the BODIPYs. Recently, the application of these seleno- or telluro-functionalized probes has been studied, mainly for the detection of ROS (reactive oxygen species) and RNS (reactive nitrogen species). The main reason for this is the usage of fluorescence quenching derived from the PeT effect, enhanced by the existence of a heavy atoms. The oxidation of one of these probes by ROS or RNS supress the PeT effect, restoring the fluorescence of the probe. Thus, great efforts have been directed to the synthesis of chalcogen-functionalized BODIPYs, and to shorter and more efficient synthetic routes. Among them, there is a growing interest in developing direct substitution reactions for rapid functionalization of the BODIPY nucleus. Recently, procedures have been developed for the direct functionalization of these nuclei with sulfur atoms, using a radical mechanism to reach the desired molecule. Thus, the present project consists of the synthesis of seleno- and telluro-functionalized BODIPY fluorescent probes, obtained through the direct functionalization of the C-H bond by radical. The proposed method has no precedent for the synthesis of compounds with selenium or tellurium. (AU)

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