Person:
Moya Cerero, Santiago De La

First Name

Santiago De La

Last Name

Moya Cerero

URI

https://hdl.handle.net/20.500.14352/76266

Affiliation

Universidad Complutense de Madrid

Faculty / Institute

Ciencias Químicas

Department

Química Orgánica

Area

Química Orgánica

Identifiers

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Search Results

Now showing 1 - 10 of 15

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 Carlos
An 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.
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 La
Boosted 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 cassettes
Preparation of dipyrrins from F-BODIPYs by treatment with methanesulfonic acids
(RSC Advances, 2015) Urieta Mora, Javier; Lora Maroto, Beatriz; Moreno Jiménez, Florencio; Rodríguez Agarrabeitia, Antonia; Ortiz García, María Josefa; Moya Cerero, Santiago De La
An alternative metal-free soft procedure for the preparation of dipyrrins from F-BODIPYs is reported. The new method makes possible to obtain certain dipyrrin derivatives that were unaccessible from F-BODIPYs to date. To demonstrate the ability of the new procedure, dipyrrins having highly reactive groups, such as chloro, cyano or acetoxyl, have been easily obtained from the corresponding F-BODIPY, which shows the synthetic utility of the reported methodology.
Bis(haloBODIPYs) with Labile Helicity: Valuable Simple Organic Molecules That Enable Circularly Polarized Luminescence
(Chemistry: a european journal, 2016) Ray Leiva, César; Márquez Sánchez-Carnerero, Esther María; Moreno Jiménez, Florencio; Lora Maroto, Beatriz; Rodríguez Agarrabeitia, Antonia; Ortiz García, María Josefa; López Arbeloa, Íñigo María; Bañuelos Prieto, Jorge; Cohovi, Komlan D.; Lunkley, jamie L.; Muller, Gilles; Moya Cerero, Santiago De La
Simple organic molecules (SOM) based on bis(haloBODIPY) are shown to enable circularly polarized luminescence (CPL), giving rise to a new structural design for technologically valuable CPL-SOMs. The established design comprises together synthetic accessibility, labile helicity, possibility of reversing the handedness of the circularly polarized emission, and reactive functional groups, making it unique and attractive as advantageous platform for the development of smart CPL-SOMs.
Controlling Vilsmeier-Haack processes in meso-methylBODIPYs: A new way to modulate finely photophysical properties in boron dipyrromethenes
(Dyes and Pigments, 2017) Palao Utiel, Eduardo; Montalvillo Jiménez, Laura; Esnal Martínez, Ixone; Prieto Montero, Ruth; Rodríguez Agarrabeitia, Antonia; García Moreno, Inmaculada; Bañuelos Prieto, Jorge; López Arbeloa, Íñigo María; Moya Cerero, Santiago De La; Ortiz García, María Josefa
In the herein work we report the fine and selective control of competitive processes when submitting meso-methylBODIPYs to Vilsmeier-Haack reaction conditions. These competitive processes generate BODIPYs with opposed photophysical properties, from highly fluorescent dyes enabling laser emission, to non-fluorescent singlet-oxygen photosensitizers. The synthetic control is exerted on the basis of the structure of the starting BODIPY, as well as the electrophilic character (hard or soft) of the formylating reagent.
Circularly Polarized Luminescence from Simple Organic Molecules
(Chemistry: a european journal, 2015) Márquez Sánchez-Carnerero, Esther María; Rodríguez Agarrabeitia, Antonia; Moreno Jiménez, Florencio; Lora Maroto, Beatriz; Muller, Gilles; Ortiz García, María Josefa; Moya Cerero, Santiago De La
This article aims to show the identity of “circularly polarized luminescent active simple organic molecules” as a new concept in organic chemistry due to the potential interest of these molecules, as availed by the exponentially growing number of research articles related to them. In particular, it describes and highlights the interest and difficulty in developing chiral simple (small and non-aggregated) organic molecules able to emit left- or right-circularly polarized light efficiently, the efforts realized up to now to reach this challenging objective, and the most significant milestones achieved to date. General guidelines for the preparation of these interesting molecules are also presented.
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 Josefa
We 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.
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.
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 José
Endowing 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.
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 Carlos
An 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.