Person:
Moreno Jiménez, Florencio

First Name

Florencio

Last Name

Moreno Jiménez

URI

https://hdl.handle.net/20.500.14352/79918

Affiliation

Universidad Complutense de Madrid

Faculty / Institute

Óptica y Optometría

Department

Química Orgánica

Area

Química Orgánica

Identifiers

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Now showing 1 - 10 of 10

Exploring N-BODIPYs as Privileged Scaffolds to Build Off/On Fluorescent Sensors by PET
(Proceedings, 2019) Ray Leiva, César; Schad, Christopher; Avellanal-Zaballa, Edurne; Moreno Jiménez, Florencio; Bañuelos, Jorge; Maroto, Beatriz Lora; Moya Cerero, Santiago de la
A new N-boron dipyrromethene (N-BODIPY) substituted with a crown ether moiety has been synthesized by reaction of an F-BODIPY with a crown-ether-substituted bis(sulfonamide). The workability of this N-BODIPY as an off/on sensor for cations by modulation of a photoinduced electron transfer (PET) is explored. The new N-BODIPY demonstrates the possibilities of functionalization of these still unexplored but promising dyes.
Chiral Organic Dyes Endowed with Circularly Polarized Laser Emission
(Journal of Physical Chemistry C, 2017) Jiménez González, Josué; Cerdán Pedraza, Luis; Moreno Jiménez, Florencio; Maroto, Beatriz Lora; García Moreno, Inmaculada; Lunkley, Jamie L.; Muller, Gilles; Moya Cerero, Santiago de la
The direct generation of efficient, tunable, and switchable circularly polarized laser emission (CPLE) would have far-reaching implications in photonics and material sciences. In this paper, we describe the first chiral simple organic molecules (SOMs) capable of simultaneously sustaining significant chemical robustness, high fluorescence quantum yields, and circularly polarized luminescence (CPL) ellipticity levels (|glum|) comparable to those of similar CPL-SOMs. All these parameters altogether enable efficient laser emission and CPLE with ellipticity levels 2 orders of magnitude stronger than the intrinsic CPL ones.
N-BODIPYs Come into Play: Smart Dyes for Photonic Materials
(Chemistry: a european journal, 2017) Ray Leiva, César; Díaz Casado, Laura; Avellanal-Zaballa, Edurne; Bañuelos Prieto, Jorge; Cerdán Pedraza, Luis; García Moreno, Inmaculada; Moreno Jiménez, Florencio; Maroto, Beatriz Lora; López Arbeloa, Íñigo María; Moya Cerero, Santiago de la
N-BODIPYs (diaminoboron dipyrromethenes) are unveiled as a new family of BODIPY dyes with huge technological potential. Synthetic access to these systems has been gained through a judicious design focused on stabilizing the involved diaminoboron chelate. Once stabilized, the obtained N-BODIPYs retain the effective photophysical behavior exhibited by other boron-substituted BODIPYs, such as O-BODIPYs. However, key bonding features of nitrogen compared to those of oxygen (enhanced bond valence and different bond directionality) open up new possibilities forfunctionalizing BODIPYs, allowing an increase in the number of pendant moieties (from two in O-BODIPYs, up to four in N-BODIPYs) near the chromophore and, therefore, greater control of the photophysics. As a proof of concept, the following findings are discussed: (1) the low-cost and straightforward synthesis of a selected series of N-BODIPYs; (2) their outstanding photophysical properties compared to those of related effective dyes (excellent emission signatures, including fluorescence in the solid state; notable lasing capacities in the liquid phase and when doped into polymers; improved laser performance compared to the parent F-BODIPYs); (3) the versatility of the diaminoboron moiety in allowing the generation of multifunctionalized BODIPYs, permitting access to both symmetric and asymmetric dyes; (4) the capability of such versatility to finely modulate the dye photophysics towards different photonic applications, from lasing to chemosensing.
BINOLated aminostyryl BODIPYs: a workable organic molecular platform for NIR circularly polarized luminescence
(Chemical Communications, 2021) Jiménez González, Josué; Díaz Norambuena, Carolina; Serrano Villar, Sergio; Ma, Shing Cho; Moreno Jiménez, Florencio; Maroto, Beatriz Lora; Bañuelos Prieto, Jorge; Muller, Gilles; Moya Cerero, Santiago de la
The accessible at-boron-BINOLated 3,5-bis(4-aminostyryl)ated BODIPY scaffold is highlighted as a workable platform for developing enantiopure small organic molecules exhibiting CPL in the NIR region, even in water solution, the latter being key for CPL-based bioapplications. Synthetic simplicity, noticeable chiroptical efficiency in the NIR and the possibility to access water-soluble emitters pave the way for advancing CPL tools based on organic emitters and NI radiation.
Modulating ICT emission: a new strategy to manipulate the CPL sign in chiral emitters
(Chemical Communications, 2019) Jiménez González, Josué; Moreno Jiménez, Florencio; Maroto, Beatriz Lora; Cabreros, Trevor A.; Huy, Angelenia S.; Muller, Gilles; Bañuelos Prieto, Jorge; Moya Cerero, Santiago de la
A new strategy to manipulate the circularly polarized luminescence (CPL) handedness in chiral emitters, based on modulating the population of an emissive ICT state, is proposed. Such a strategy is particularly interesting for conformationally rigid and non-aggregating chiral organic emitters, opening up new perspectives for the development of CPL application based on organic molecules
BOPHYs versus BODIPYs: A comparison of their performance as effective multi-function organic dyes
(Dyes and Pigments, 2019) Sola Llano, Rebeca; Jiménez, J.; Avellanal Zaballa, Edurne; Johnson, M.; Cabreros, Trevor A.; Moreno Jiménez, Florencio; Maroto, Beatriz Lora; Muller, Gilles; Bañuelos Prieto, Jorge; Cerdán Pedraza, Luis; García Moreno, Inmaculada; Moya Cerero, Santiago de la
The computationally-aided photophysical and lasing properties of a selected battery of BOPHYs are described and compared to those of related BODIPY counterparts. The present joined theoretical-experimental study helps to put into context the weaknesses and strengths of both dye families under different irradiation conditions. The chemical versatility of the BOPHY scaffold has been also comparatively explored to modulate key photonic properties towards the development of red-emitting dyes, chiroptical dyes and singlet oxygen photosensitizers. Thus, BOPHY BINOLation by fluorine substitution with enantiopure BINOLs endows the BOPHY chromophore with chiroptical activity, as supporting by the simulated circular dichroism, decreasing deeply its fluorescent response due to the promotion of fluorescence-quenching intramolecular charge transfer (ICT). Interestingly, the sole alkylation of the BOPHY core strongly modulates the promotion of ICT, allowing the generation of highly bright BINOL-based BOPHY dyes. Moreover, 3,3′ dibromoBINOLating BOPHYs can easily achieve singlet-oxygen photogeneration, owing to spin-orbit coupling mediated by heavy-atom effect feasible in view of the theoretically predicted disposition of the bromines surrounding the chromophore. From this background, we have established the master guidelines to design bright fluorophores and laser dyes, photosensitizers for singlet oxygen production and chiroptical dyes based on BOPHYs. The possibility to finely mix and balance such properties in angiven molecular scaffold outstands BOPHYs as promising dyes competing with the well-settled BODIPY dyes
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 la
A 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.
Multichromophoric COO-BODIPYs: an advantageous design for the development of energy transfer and electron transfer systems
(Chemical Communications, 2021) Ray Leiva, César; Schad, Christopher; Avellanal Zaballa, Edurne; Moreno Jiménez, Florencio; Maroto, Beatriz Lora; Bañuelos Prieto, Jorge; García Moreno, Inmaculada; Moya Cerero, Santiago de la
COO-BODIPYs are highlighted as cutting edge scaffolds for easy access to a new generation of multichromophoric architectures with enhanced (photo)chemical stability, showing either boosted capability for excitation energy transfer, glow fluorescence and laser emission, or photoinduced electron transfer. The new finding paves the way for the rapid development of smarter organic dyes for advancing photonics and optoelectronics
C*-BODIPYs: Exploring a New Strategy to Transfer Chirality towards BODIPY Chiroptics
(Proceedings, 2020) Jiménez González, Josué; Sánchez Camacho, Juan; Moreno Jiménez, Florencio; Rodríguez Agarrabeitia, Antonia; Arbeloa, Teresa; Cabreros, Trevor A.; Muller, Gilles; Bañuelos, Jorge; Maroto, Beatriz Lora; Moya Cerero, Santiago de la
C*-BODIPYs, that is, boron dipyrromethenes (BODIPYs) which have chiral carbons attached directly to the boron center, are introduced for the first time. These novel chiral BODIPYs mean a new strategy for the chiral perturbation of the inherently achiral BODIPY chromophore that is directed to enable chiroptical properties. Their preparation is very simple and only implies the complexation of a dipyrrin with an enantiopure dialkylborane having boron bonded to chiral carbons.
BCl3‑Activated Synthesis of COO-BODIPY Laser Dyes: General Scope and High Yields under Mild Conditions
(Journal of organic chemistry, 2020) Ray Leiva, César; Schad, Christopher; Moreno Jiménez, Florencio; Maroto, Beatriz Lora; Bañuelos Prieto, Jorge; Arbeloa, Teresa; García Moreno, Inmaculada; Villafuerte, Cassie; Muller, Gilles; Moya Cerero, Santiago de la
A general and straightforward method for the synthesis of COO-BODIPYs from F-BODIPYs and carboxylic acids is established. The method is based on the use of boron trichloride to activate the involved substitution of fluorine, which leads to high yields through rapid reactions under soft conditions. This mild method opens the way to unprecedented laser dyes with outstanding efficiencies and photostabilities, which are difficult to obtain by the current methods.