Versatile Metal-Free Arylation of BODIPY and Bis(BF₂) Chromophores by Using Arylazosulfones in a Sunflow System

Author(s)

de Melo, Shaiani Maria Gil ; dos Santos, Thiago ; Silva, Daniel Gedder ; Martins, Yugo Araujo ; Eckhardt, Paul ; Lopez, Renata Fonseca Vianna ; Opatz, Till ; Protti, Stefano ; da Silva Emery, Flavio

• Document type: Journal article
• Source: CHEMISTRY-A EUROPEAN JOURNAL; v. 30, n. 61, p. 9-pg., 2024-10-04.

Abstract

BODIPYs have a well-established role in biological sciences as chemosensors and versatile biological markers due to their chemical reactivity, which allows for fine-tuning of their photophysical characteristics. In this work, we combined the unique reactivity of arylazo sulfones with the advantages of a "sunflow" reactor to develop a fast, efficient, and versatile method for the photochemical arylation of BODIPYs and other chromophores. This approach resulted in red-shifted emitting fluorophores due to extended electronic delocalization at the 3- and 5-positions of the BODIPY core. This method represents an advantageous approach for BODIPY functionalization compared to existing strategies. (AU)

• FAPESP's process: 17/22001-0 - Synthesis and evaluation of new heterocyclic compounds as potential antitrypanosomal agents
• Grantee: Daniel Gedder Silva
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 22/03521-0 - Investigation of physical methods associated with drug delivery systems in the local immune and antimicrobial response
• Grantee: Renata Fonseca Vianna Lopez
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 21/11899-0 - Development of novel series of potent and selective heterocyclic compounds as anti-infectives agents
• Grantee: Daniel Gedder Silva
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor
• FAPESP's process: 17/21146-4 - Heterocyclic chemistry and epigenetic for the development of library of compounds for medicinal chemistry purposes.
• Grantee: Flavio da Silva Emery
• Support Opportunities: Regular Research Grants