Person: Moya Cerero, Santiago De La
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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
7 results
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Now showing 1 - 7 of 7
Item 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 JosefaIn 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.Item 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 LaThis 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.Item Rational Design of Advanced Photosensitizers Based on Orthogonal BODIPY Dimers to Finely Modulate Singlet Oxygen Generation(Chemistry: a european journal, 2017) Epelde Elezcano, Nerea; Palao Utiel, Eduardo; Manzano, Hegoi; Prieto Castañeda, Alejandro; Rodríguez Agarrabeitia, Antonia; Tabero Truchado, Andrea; Villanueva Oroquieta, Ángeles; Moya Cerero, Santiago De La; López Arbeloa, Íñigo María; Martínez Martínez, Virginia; Ortiz García, María JosefaThe synthesis, photophysical characterization, and modeling of a new library of halogen-free photosensitizers (PS) based on orthogonal boron dipyrromethene (BODIPY) dimers are reported. Herein we establish key structural factors in order to enhance singlet oxygen generation by judiciously choosing the substitution patterns according to key electronic effects and synthetic accessibility factors. The photosensitization mechanism of orthogonal BODIPY dimers is demonstrated to be strongly related to their intrinsic intramolecular charge transfer (ICT) character through the spin-orbit charge-transfer intersystem crossing (SOCT-ISC) mechanism. Thus, singlet oxygen generation can be effectively modulated through the solvent polarity and the presence of electron-donating or withdrawing groups in one of the BODIPY units. The photodynamic therapy (PDT) activity is demonstrated by in vitro experiments, showing that selected photosensitizers are efficiently internalized into HeLa cells, exhibiting low dark toxicity and high phototoxicity, even at low PS concentration (0.05–5×10−6 m).Item 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 LaAn 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.Item Exploring the Application of the Negishi Reaction of HaloBODIPYs: Generality, Regioselectivity, and Synthetic Utility in the Development of BODIPY Laser Dyes(Journal of Organic Chemistry, 2016) Palao Utiel, Eduardo; Durán Sampedro, Gonzalo; Moya Cerero, Santiago De La; Madrid, Miriam; García López, Carmen; Rodríguez Agarrabeitia, Antonia; Verbelen, Bram; Dehaen, Wim; Boens, Nöel; Ortiz García, María JosefaThe generality of the palladium-catalyzed C–C coupling Negishi reaction when applied to haloBODIPYs is demonstrated on the basis of selected starting BODIPYs, including polyhalogenated and/or asymmetrical systems, and organozinc reagents. This reaction is an interesting synthetic tool in BODIPY chemistry, mainly because it allows a valuable regioselective postfunctionalization of BODIPY chromophores with different functional groups. In this way, functional patterns that are difficult to obtain by other procedures (e.g., asymmetrically functionalized BODIPYs involving halogenated positions) can now be made. The regioselectivity is achieved by controlling the reaction conditions and is based on almost-general reactivity preferences, and the nature of the involved halogens and their positions. This ability is exemplified by the preparation of a series of new BODIPY dyes with unprecedented substitution patterns allowing noticeable lasing properties.Item Speeding up heterogeneous catalysis with an improved highly reusable catalyst for the preparation of enantioenriched secondary alcohols(Reactive and Functional Polymers, 2017) Sánchez Carnerero, Esther M. Márquez; Sandoval Torrientes, Rafael; Urieta Mora, Javier; Moreno Jiménez, Florencio; Maroto, Beatriz Lora; Moya Cerero, Santiago De LaA new catalytic heterogeneous system, very efficient and highly reusable, for the preparation of enantioenriched secondary alcohols through the addition of diethylzinc to benzaldehyde has been developed. This system is based on a chiral bis(hydroxyamide) ligand supported on crosslinked polystyrene. The catalyst has been shown to be very efficient, leading to the corresponding secondary alcohol with an enantiomeric excess of 93% in a time as short as 2 h and using just 4% of the heterogeneous catalyst and just 1.5 equivalents of the organozinc reagent. We have demonstrated that the new catalyst is very stable and can be efficiently recycled with no decrease in yield or enantioselectivity. The presented system has an unquestionable interest for the potential transfer of the reaction to the industry by using catalytic fluidized-bed reactors.Item A versatile fluorescent molecular probe endowed with singlet oxygen generation under white-light photosensitization(Dyes and Pigments, 2017) Durán Sampedro, Gonzalo; Epelde Elezcano, Nerea; Martínez Martínez, Virginia; Esnal Martínez, Ixone; Bañuelos Prieto, Jorge; García Moreno, Inmaculada; Rodríguez Agarrabeitia, Antonia; Moya Cerero, Santiago De La; Tabero Truchado, Andrea; Lázaro Carrillo, Ana; Villanueva Oroquieta, Ángeles; Ortiz García, María Josefa; López Arbeloa, Íñigo MaríaDespite fluorescent photodynamic therapy (fluorescent-PDT) dyes are promising theranostic agents, current approaches unfortunately involve crucial shortcomings (such as, narrow absorption bands, high cost, low bio-compatibility and specificity, low dual efficiency) making difficult their clinical translation. Particularly, efficient fluorescent-PDT agents triggered under white-light, with potential application in topic solar treatments, are scarce. Here, we describe the rational development of a novel fluorescent-PDT molecular biomaterial based on BODIPY building blocks able to sustain, simultaneously, synthetic accessibility, high fluorescence and phototoxicity within a broad spectral window, biocompatibility, including low dark toxicity and high cell permeability with selective accumulation in lysosomes and, what is more important, excellent efficient activity triggered under white light. These all-in-one combined properties make the new dye a valuable ground platform for the development of future smarter theranostic agents.