Person: Moya Cerero, Santiago De La
Loading...
First Name
Santiago De La
Last Name
Moya Cerero
Affiliation
Universidad Complutense de Madrid
Faculty / Institute
Ciencias Químicas
Department
Química Orgánica
Area
Química Orgánica
Identifiers
9 results
Search Results
Now showing 1 - 9 of 9
Item Easy and accurate computation of energy barriers for carbocation solvation: an expeditious tool to face carbocation chemistry(Physical Chemistry Chemical Physics, 2023) García Martínez, Antonio; Siehl, Hans-Ulrich; Moya Cerero, Santiago De La; Gómez Calzada, Pedro CarlosAn expeditious procedure for the challenging computation of the free energy barriers (DGa) for the solvation of carbocations is presented. This procedure is based on Marcus Theory (MT) and the popular B3LYP/6-31G(d)// PCM method, and it allows the easy, accurate and inexpensive prediction of these barriers for carbocations of very different stability. This method was validated by the fair mean absolute error (ca. 1.5 kcal mol1 ) achieved in the prediction of 19 known experimental barriers covering a range of ca. 50 kcal mol1 . Interestingly, the new procedure also uses an original method for the calculation of the required inner reorganization energy (Li ) and free energy of reaction (DG). This procedure should pave the way to face computationally the pivotal issue of carbocation chemistry and could be easily extended to any bimolecular organic reaction.Item Spiranic BODIPYs: a ground-breaking design to improve the energy transfer in molecular cassettes(Chemical Communications, 2014) Márquez Sánchez-Carnerero, Esther María; Gartzia-Rivero, Leire; Moreno Jiménez, Florencio; Lora Maroto, Beatriz; Rodríguez Agarrabeitia, Antonia; Ortiz García, María Josefa; Bañuelos Prieto, Jorge; López Arbeloa, Íñigo María; Moya Cerero, Santiago De LaBoosted excitation energy transfer in spiranic O BODIPY/polyarenecassettes, when compared with the parent non-spiranic (flexible) system, is highlighted as a proof for the ability of a new structural design to improve the energy transfer in molecular cassettesItem 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 BODIPYs revealing lipid droplets as valuable targets for photodynamic theragnosis(Chemical Communications, 2019) Tabero, Andrea; García-Garrido, Fernando; Prieto Castañeda, Alejandro; Palao, Eduardo; Rodríguez Agarrabeitia, Antonia; García-Moreno, Inmaculada; Villanueva Valdés, Miguel Ángel; Moya Cerero, Santiago De La; Ortiz, María JoséEndowing BODIPY PDT agents with the ability to probe lipid droplets is demonstrated to boost their phototoxicity, allowing the efficient use of highly fluorescent dyes (poor ROS sensitizers) as phototoxic agents. Conversely, this fact opens the way to the development of highly bright ROS photosensitizers for performing photodynamic theragnosis (fluorescence bioimaging and photodynamic therapy) from a single simple agent. On the other hand, the noticeable capability of some of the reported dyes to probe lipid droplets in different cell lines under different conditions reveals their use as privileged probes for advancing the study of interesting lipid droplets by fluorescence microscopy.Item Easy and accurate computation of energy barriers for carbocation solvation: an expeditious tool to face carbocation chemistry(Physical Chemistry Chemical Physics, 2023) García Martínez, Antonio; Siehl, Hans-Ulrich; Moya Cerero, Santiago De La; Gómez Calzada, Pedro CarlosAn expeditious procedure for the challenging computation of the free energy barriers (DGa) for the solvation of carbocations is presented. This procedure is based on Marcus Theory (MT) and the popular B3LYP/6-31G(d)// PCM method, and it allows the easy, accurate and inexpensive prediction of these barriers for carbocations of very different stability. This method was validated by the fair mean absolute error (ca. 1.5 kcal mol1 ) achieved in the prediction of 19 known experimental barriers covering a range of ca. 50 kcal mol1 . Interestingly, the new procedure also uses an original method for the calculation of the required inner reorganization energy (Li ) and free energy of reaction (DG). This procedure should pave the way to face computationally the pivotal issue of carbocation chemistry and could be easily extended to any bimolecular organic reaction.Item Dissimilar-at-boron N-BODIPYs: from light-harvesting multichromophoric arrays to CPL-bright chiral-at-boron BODIPYs(Organic Chemistry Frontiers, 2023) Ray, César; Avellanal-Zaballa, Edurne; Muñoz Úbeda, Mónica; Colligan, Jessica; Moreno Jiménez, Florencio; Muller, Gilles ; López Montero, Iván; Bañuelos, Jorge; Lora Maroto, Beatriz; Moya Cerero, Santiago De LaWe report a workable and easy approach for the direct post-multifunctionalization of common BODIPYs (F-BODIPYs) with minimal interference to the starting photophysical behavior. It entails the easy transformation of an F-BODIPY into the corresponding N-BODIPY by using a dissimilarly-N,N′-disubstituted bis(sulfonamide), which is easily obtained from ethane-1,2-diamine. This approach is exemplified by the rapid synthesis of a selected battery of unprecedented dissimilar-at-boron N-BODIPYs, which are rationally designed to act as efficient multichromophoric arrays for light harvesting by excitation energy transfer, as specific bioprobes for fluorescent imaging, or as efficient chiroptical dyes exhibiting visible circular dichroism and circularly polarized luminescence. Noticeably, this approach has led to the synthesis of the first CPL-bright chiral-at-boron BODIPYs, a significant novelty in BODIPY chemistry and CPL emittersItem 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 Negishi reaction in BODIPY dyes. Unprecedented alkylation by palladium-catalyzed C–C coupling in boron dipyrromethene derivatives(RSC Advances, 2014) Durán Sampedro, Gonzalo; Palao, Eduardo; Rodríguez Agarrabeitia, Antonia; Moya Cerero, Santiago De La; Boens, Noël; Ortiz García, María JosefaNegishi reactions of 3-halogen and 3,5-dihalogen substituted BODIPYs with different organozinc reagents are reported as the first examples of this valuable palladium-catalyzed C–C coupling reaction into the family of the BODIPY dyes. It is demonstrated that the Negishi coupling is especially useful for obtaining interesting alkylated BODIPYs, including synthetically-valuable asymmetrically-3,5-disubstituted BODIPYs.