Optimized synthesis of dipyrromethanes and direct selenofunctionalization of BODIPYs cores

Author(s)

João Luiz Petrarca de Albuquerque

• Document type: Master's Dissertation
• Press: São Paulo.
• Institution: Universidade de São Paulo (USP). Conjunto das Químicas (IQ e FCF) (CQ/DBDCQ)
• Defense date: 2022-06-07

Examining board members

Alcindo Aparecido dos Santos; Cristiano Raminelli

• Advisor: Alcindo Aparecido dos Santos

Abstract

Over the past few decades, there has been a growing interest in the synthesis of fluorescent compounds and their application as probes, especially BODIPYs (boron-dipyrromethene). Recently, studies on the application of the selenoBODIPYs probes for the detection of ROS (reactive oxygen species) and RNS (reactive nitrogen species) are being conducted. The oxidation of selenium atoms by ROS or RNS suppresses the PeT effect, restoring the probes fluorescence. Thus, the synthesis of selenoBODIPYs rises as an interesting strategy, in which shorter and more effective routes will provide major advances in the applications of these fluorescent agents. Direct substitution reactions, leading to a quick core functionalization are among the most interesting strategies. The present work reports a new approach for the direct selenofunctionalization of BODIPY cores utilizing diselenides and organic peroxides and hypotheses on the mechanisms were elaborated. In addition, a new methodology was developed for the synthesis of BODIPYs precursors (dipyrromethane), which does not require purification and can be used directly in the next step. Their purity was verified by quantitative NMR; a method was developed for reutilizing the reaction media on new reactions, generating fewer residues. (AU)

• FAPESP's process: 20/04782-7 - Direct seleno- and telluro-functionalization of positions 3 and 5 from the BODIPY core via radical approach
• Grantee: João Luiz Petrarca de Albuquerque
• Support Opportunities: Scholarships in Brazil - Master