Diazonium salts chemistry applied to BODIPY fluorophores

Author(s)

Shaiani Maria Gil de Melo

• Document type: Master's Dissertation
• Press: Ribeirão Preto.
• Institution: Universidade de São Paulo (USP). Faculdade de Ciências Farmacêuticas de Ribeirão Preto (PCARP/BC)
• Defense date: 2016-09-30

Examining board members

Flavio da Silva Emery; Eufrânio Nunes da Silva Júnior; Roberto Santana da Silva

• Advisor: Flavio da Silva Emery

Abstract

BODIPYs are fluorescent compounds which have a wide range of technological applications in different areas of knowledge. They have remarkable presence in the literature because of their synthetic and photochemical properties. However, the chemical reactivity of these fluorophores are not fully known. Considering this, our study applied the diazonium salts chemistry to BODIPYs aiming to explore the structure diversification of these fluorophores. Three different methods were used to obtain the diazo derivatives of BODIPYs: NOBF4, NaNO2/HCl and NaNO2/HBF4. The method using the NOBF4 instead of afford the diazotized compound as expected, a nitrosylated compound was obtained. When NaNO2/HCl was used, the diazotized compound was obtained in situ, followed by diazo coupling reaction. The best yields diazo coupling reactions were obtained when NaNO2/HBF4 was used. The reactions described in our work showed new possibilities of chemical tractability of BODIPY compounds. (AU)

• FAPESP's process: 14/18973-8 - Application of diazonium salts chemistry in structural modification of BODIPY fluorophores
• Grantee: Shaiani Maria Gil de Melo
• Support Opportunities: Scholarships in Brazil - Master