Extended BODIPYs as Red-NIR Laser Radiation Sources with Emission from 610 nm to 750 nm

• Published in: Molecules (Basel, Switzerland) Vol. 28; no. 12; p. 4750
• Main Authors: Oliden-Sánchez, Ainhoa, Alvarado-Martínez, Enrique, Ramírez-Ornelas, Diana E, Vázquez, Miguel A, Avellanal-Zaballa, Edurne, Bañuelos, Jorge, Peña-Cabrera, Eduardo
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 13.06.2023; MDPI
• Subjects: Acids; BODIPY; Charge transfer; Chemical reactions; Cross coupling; Dyes; dyes/pigments; Efficiency; Emissions; Fluorescence; Laser radiation; laser spectroscopy; Lasers; Near infrared radiation; Phenyls; Radiation; Radiation sources; Substitution reactions; Thiophene; Visible spectrum; dyes/pigments; BODIPY; laser spectroscopy; fluorescence; charge transfer
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28124750

Herein, we report the synthetic access to a set of π-extended BODIPYs featuring a penta-arylated (phenyl and/or thiophene) dipyrrin framework. We take advantage of the full chemoselective control of 8-methylthio-2,3,5,6-tetrabromoBODIPY when we conduct the Liebeskind-Srogl cross-coupling (LSCC) to functionalize exclusively the -position, followed by the tetra-Suzuki reaction to arylate the halogenated sites. All these laser dyes display absorption and emission bands in the red edge of the visible spectrum reaching the near-infrared with thiophene functionalization. The emission efficiency, both fluorescence and laser, of the polyphenylBODIPYs can be enhanced upon decoration of the peripheral phenyls with electron donor/acceptor groups at positions. Alternatively, the polythiopheneBODIPYs show an astonishing laser performance despite the charge transfer character of the emitting state. Therefore, these BODIPYs are suitable as a palette of stable and bright laser sources covering the spectral region from 610 nm to 750 nm.