Carboxylates versus Fluorines: Boosting the Emission Properties of Commercial BODIPYs in Liquid and Solid Media

• Published in: Advanced functional materials 2013-09, Vol.23 (34), p.4195-4205
• Main Authors: Durán-Sampedro, Gonzalo, Agarrabeitia, Antonia R., Cerdán, Luis, Pérez-Ojeda, M. Eugenia, Costela, Angel, García-Moreno, Inmaculada, Esnal, Ixone, Bañuelos, Jorge, Arbeloa, Iñigo López, Ortiz, María J.
• Format: Article
• Language: English
• Subjects: Carboxylates; dye lasers; Dyes; Emission; Fluorine; laser materials; Lasers; Liquids; O-BODIPYs; optically active materials; polymeric materials; Polymethyl methacrylates; Strategy
• ISSN: 1616-301X; 1616-3028
• DOI: 10.1002/adfm.201300198

A new and facile strategy for the development of photonic materials is presented that fufills the conditions of being efficient, stable, and tunable laser emitters over the visible region of spectrum, with the possibility of being easily processable and cost‐effective. This approach uses poly(methyl methacrylate) (PMMA) as a host for new dyes with improved efficiency and photostability synthesized. Using a simple protocol, fluorine atoms in the commercial (4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene) (F‐BODIPY) by carboxylate groups. The new O‐BODIPYs exhibit enhanced optical properties and laser behavior both in the liquid and solid phases compared to their commercial analogues. Lasing efficiencies up to 2.6 times higher than those recorded for the commercial dyes are registered with high photostabilities since the laser output remain at 80% of the initial value after 100 000 pump pulses in the same position of the sample at a repetition rate of 30 Hz; the corresponding commercial dye entirely loses its laser action after only 12 000 pump pulses. Distributed feedback laser emission is demonstrated with organic films incorporating new O‐BODIPYs deposited onto quartz substrates engraved with appropriated periodical structures. These dyes exhibit laser thresholds up to two times lower than those of the corresponding parent dyes with lasing intensities up to one order of magnitude higher. The development of new O‐BODIPYs, synthesized via the replacement of fluorine atoms by carboxylate groups in commercial (4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene) (F‐BODIPYs), is a successful strategy to obtain optimized laser dyes. Poly(methyl methacrylate) (PMMA) doped with these new derivatives leads to laser materials that are economically affordable and have optimized emission properties in the visible spectral region.