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Synthetic Approach to Readily Accessible Benzofuran-Fused Borondipyrromethenes as Red-Emitting Laser Dyes

2019; American Chemical Society; Volume: 84; Issue: 5 Linguagem: Inglês

10.1021/acs.joc.8b02933

1520-6904

José L. Belmonte‐Vázquez, Edurne Avellanal‐Zaballa, Ernesto Enríquez-Palacios, Luis Cerdán, Ixone Esnal, Jorge Bañuelos, Clarisa Villegas-Gómez, Íñigo López‐Arbeloa, Eduardo Peña‐Cabrera,

Nanoplatforms for cancer theranostics

We took advantage of the chemoselective meso-functionalization of 2,3,5,6-tetrabromo-8-methylthioBODIPY 6 to prepare a series of 2,3,5,6-tetrabromo-8-arylBODIPY derivatives suitable for SNAr substitution reactions with phenols exclusively at positions 3 and 5. Pd(0)-catalyzed intramolecular arylation reaction ensued on the remaining brominated positions 2 and 6 to give a new family of benzofuran-fused BODIPY dyes. This method utilizes readily available starting materials and allows for the preparation of the title compounds with excellent functional group tolerance. Moreover, it was demonstrated that the methodology described herein is amenable for the incorporation of biomolecules. The photophysical and lasing properties of the benzofuran-fused BODIPY dyes were thoroughly analyzed with the aid of electrochemical measurements and quantum mechanical simulations. These dyes show bright and intriguing emission (both fluorescence and laser) toward the red edge of the visible spectrum with remarkable tolerance under strong and continuous irradiation.