Person: Rodríguez Agarrabeitia, Antonia
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First Name
Antonia
Last Name
Rodríguez Agarrabeitia
Affiliation
Universidad Complutense de Madrid
Faculty / Institute
Óptica y Optometría
Department
Química Orgánica
Area
Química Orgánica
Identifiers
8 results
Search Results
Now showing 1 - 8 of 8
Item Coumarin–BODIPY hybrids by heteroatom linkage: versatile, tunable and photostable dye lasers for UV irradiation(Physical Chemistry Chemical Physics, 2015) Esnal, Ixone; Duran-Sampedro, Gonzalo; Rodríguez Agarrabeitia, Antonia; Bañuelos, Jorge; García-Moreno, Inmaculada; Macías, Maria Ángeles ; Peña-Cabrera, Eduardo; López-Arbeloa, Iñigo; De la Moya, Santiago; Ortiz, Maria JoséLinking amino and hydroxycoumarins to BODIPYs through the amino or hydroxyl group lets the easy construction of unprecedented photostable coumarin–BODIPY hybrids with broadened and enhanced absorption in the UV spectral region, and outstanding wavelength-tunable laser action within the green-to-red spectral region (∼520–680 nm). These laser dyes allow the generation of a valuable tunable UV (∼260–350 nm) laser source by frequency doubling, which is essential to study accurately the photochemistry of biological molecules under solar irradiation. The tunability is achieved by selecting the substitution pattern of the hybrid. Key factors are the linking heteroatom (nitrogen vs. oxygen), the number of coumarin units joined to the BODIPY framework and the involved linking positions.Item Development of Geometry-Controlled All-Orthogonal BODIPY Trimers for Photodynamic Therapy and Phototheragnosis(Organic Letters, 2022) Prieto Castañeda, Alejandro; García Garrido, Fernando; Díaz Norambuena, Carolina; Escriche Navarro, Blanca; García Fernández, Alba; Bañuelos, Jorge; Rebollar, Esther; García Moreno, Inmaculada; Martínez Máñez, Ramón; Moya Cerero, Santiago De La; Rodríguez Agarrabeitia, Antonia; Ortiz García, María JosefaWe have established an easy synthetic protocol for selectively developing all-orthogonal BODIPY trimers with unprecedented geometries on the basis of selecting methyl oxidation versus electrophilic formylation of key dimeric precursors. Photophysical characterization together with biological assays unraveled the most suitable BODIPY−BODIPY geometrical arrangements within the trimer, forcing them to serve as molecular platforms for the development of new, advanced heavy-atom-free photosensitizers for photodynamic therapy and phototheragnosis.Item Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers(International Journal of Molecular Sciences, 2023) Díaz Norambuena, Carolina; Avellanal Zaballa, Edurne; Prieto Castañeda, Alejandro; Bañuelos, Jorge; de la Moya, Santiago; Rodríguez Agarrabeitia, Antonia; Moya Cerero, Santiago De La; Ortiz, María J.Heavy-atom-free photosensitizers are envisioned as the next generation of photoactive molecules for photo-theragnosis. In this approach, and after suitable irradiation, a single molecular scaffold is able to visualize and kill tumour cells by fluorescence signalling and photodynamic therapy (PDT), respectively, with minimal side effects. In this regard, BODIPY-based orthogonal dimers have irrupted as suitable candidates for this aim. Herein, we analyse the photophysical properties of a set of formyl-functionalized BODIPY dimers to ascertain their suitability as fluorescent photosensitizers. The conducted computationally aided spectroscopic study determined that the fluorescence/singlet oxygen generation dual performance of these valuable BODIPY dimers not only depends on the BODIPY-BODIPY linkage and the steric hindrance around it, but also can be modulated by proper formyl functionalization at specific chromophoric positions. Thus, we propose regioselective formylation as an effective tool to modulate such a delicate photonic balance in BODIPY-based dimeric photosensitizers. The taming of the excited-state dynamics, in particular intramolecular charge transfer as the key underlying process mediating fluorescence deactivation vs. intersystem crossing increasing, could serve to increase fluorescence for brighter bioimaging, enhance the generation of singlet oxygen for killing activity, or balance both for photo-theragnosis.Item Phosphorogenic dipyrrinato-iridium(III) complexes as photosensitizers for photodynamic therapy(Phosphorogenic dipyrrinato-iridium(III) complexes as photosensitizers for photodynamic therapy, 2021) Prieto Castañeda, Alejandro; Lérida Viso, A.; Avellanal Zaballa, Edurne; Sola Llano, rebeca; Bañuelos, Jorge; Rodríguez Agarrabeitia, Antonia; Martínez Mañez, Ramon; Ortiz García, María JosefaWe have designed and synthesized a family of Ir(III) metal complexes coordinated with two cyclometalated bisfluorophenylpyridine ligands and an ancillary dipyrromethene which is functionalized with a mesityl group (Ir(dipy)-1), an α-chloroacetyl ester (Ir(dipy)-2) or a chain containing an ammonium cation (Ir(dipy)-3). The Ir (III) complexes feature a high triplet state population enabling red phosphorescence and efficient singlet oxygen generation. Ir(dipy)-2 and Ir(dipy)-3 are demonstrated to stain cells in both one-photon and two-photon confocal imaging. Moreover, Ir(dipy)-2 and Ir(dipy)-3 produce ROS in cells upon irradiation, inducing cell death by apoptosis. Colocalization studies in SK-Mel-103 cells show that Ir(dipy)-3 is partially accumulated in mitochondria and induces upon irradiation a disruption in their morphology. Overall our studies demonstrate that the prepared Ir(III) act as photosensitizers able to kill cells under irradiation, being suitable candidates for photodynamic therapy applications.Item An asymmetric BODIPY triad with panchromatic absorption for high-performance red-edge laser emission(Chemmical Communications, 2015) Durán Sampedro, Gonzalo; Rodríguez Agarrabeitia, Antonia; Garcia-Moreno, Inmaculada ; Gartzia-Rivero, Leire; Bañuelos, Jorge; López-Arbeloa, Ínigo; Ortiz García, María Josefa; Moya Cerero, Santiago De LaA rational design of an unprecedented asym. cassette triad based entirely on BODIPY chromophores allows efficient light harvesting over the UV-vis spectral region, leading to a bright and stable red-edge laser emission via efficient energy-transfer processes.Item Chlorinated BODIPYs: Surprisingly Efficient and Highly Photostable Laser Dyes(European Journal of Organic Chemistry, 2012) Durán Sampedro, Gonzalo; Rodríguez Agarrabeitia, Antonia; García Moreno, Inmaculada; Costela, Angel; Bañuelos, Jorge; Arbeloa, Teresa; López Arbeloa, Iñigo; Chiara, Jose Luis; Ortiz García, María JosefaA series of mono‐ to hexachlorinated BODIPY dyes have been prepared in good to excellent yields through the use of chlorosuccinimide as an inexpensive halogenating reagent. This library of chlorinated dyes allowed analysis in detail, from the experimental and theoretical points of view, of the dependency of the photophysical and optical properties of the dyes on the number and positions of the chlorine substituents on their BODIPY cores. Quantum mechanical calculations predict the regioselectivity of the halogenation reaction and explain why some positions are less prone to chlorination. The new chlorinated BODIPYs exhibit enhanced laser action with respect to their non‐halogenated analogues, both in liquid solution and in the solid phase. In addition, chlorination is a facile and essentially costless protocol for overcoming important shortcomings exhibited by commercially available BODIPYs, which should favor their practical applications in optical and sensing fields.Item Carboxylates versus Fluorines: Boosting the Emission Properties of Commercial BODIPYs in Liquid and Solid Media(Advanced Functional Materials, 2013) Durán Sampedro, Gonzalo; Rodríguez Agarrabeitia, Antonia; Cerdán, Luis; Pérez Ojeda, María Eugenia; Costela, Angel; García‐Moreno, Inmaculada; Esnal, Ixone; Bañuelos, Jorge; López Arbeloa, Iñigo; Ortiz García, María JosefaA new and facile strategy for the development of photonic materials is presented that fufi lls the conditions of being effi cient, 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 effi ciency and photostability synthesized. Using a simple protocol, fl uorine atoms in the commercial (4,4-difl uoro-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 effi ciencies 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 fi lms 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.Item Increased laser action in commercial dyes from fluorination regardless of their skeleton(Laser Physics Letters, 2014) Durán Sampedro, Gonzalo; Rodríguez Agarrabeitia, Antonia; Arbeloa Lopez, Teresa; Bañuelos, Jorge; López Arbeloa, Iñigo; Chiara, José Luis; Garcia Moreno, Inmaculada; Ortiz García, María JosefaThe direct and simple fluorination of representative organic laser dyes with emission covering the entire visible spectrum, from blue to red, including Coumarin 460, Pyrromethene 546, Rhodamine 6G and Perylene Red, enhances laser efficiencies by a factor up to 1.8 with respect to the corresponding non-fluorinated parent dyes. More importantly, fluorination also significantly enhances the photostability of the dyes, even under drastic laser pumping conditions.