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The contamination of water resources with various pharmaceutical residues confirms the importance of developing their removal methods by introducing new efficient adsorbents. In this study, the potential of imidazole modified clinochlore (Im@clin) as a new adsorbent for removal of Ibuprofen (IBP) from polluted water was assessed. The characterization studies of synthesized Im@clin by using X-ray photoelectron spectroscopy (XPS), transmission electron microscopy (TEM), scanning electron microscope (SEM), SEM-mapping, Fourier-transform infrared spectroscopy (FTIR), and thermogravimetric analysis (TGA) confirms that the Im@clin is convenient for adsorption. Then, the adsorption capacity of synthesized Im@clin was assessed with regard to removing ibuprofen under different conditions such as varying pH levels of IBP solutions (2–11), initial IBP concentrations (5–200 mg L−1), contact time (5–60 min), and the amount of Im@clin as adsorbent (1.7–33.3 g L−1). The results demonstrate that maximum adsorption capacity of Im@clin for removal of IBP in aqueous solutions is 5.8 mg g−1. The pseudo-second-order and the Langmuir model successfully represented the adsorption kinetic and isotherm of procedure. The thermodynamic parameters such as ΔG0 (the Gibbs free-energy difference), ΔH0 (Enthalpy change difference), and ΔS° (Entropy change difference) are calculated. The endothermic nature (ΔH0 16.19 kJ mol−1) and spontaneous nature (Gibbs free energy change, ΔG0 − 2.03 kJ mol−1) of the IBP adsorption process by Im@clin were confirmed and this process is entropy derived (ΔS0 0.06 kJ mol−1). The authors are grateful to Institute for Advanced Studies in Basic Sciences (IASBS) Research Council, Zanjan University and Iran National Science Foundation (INSF-Grant number of 4000252) for support of this work. We also gratefully acknowledge financial support from the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P and CTQ2014-51912-REDC), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P and CTQ2016-81797-REDC), the Generalitat Valenciana (PROMETEOII/2014/017) and the University of Alicante.

α-Oxy ketones, easily accessible by conventional routes, can be selectively deprotonated generating an enolate intermediate, which upon treatment with paraformaldehyde undergoes an aldol–Tishchenko reaction, leading to relevant 1,2,3-triol fragments in a totally diastereoselective manner. The excellent stereocontrol in the generation of a quaternary stereocenter is attributed to stereoelectronic effects in the Evans intermediate. This methodology allows overcoming some limitations of our previously reported strategy, based on the reaction of α-lithiobenzyl ethers with esters and paraformaldehyde, broadening the scope of the obtained polyols. Synthetic applications of this process include the preparation of a new dilignol model and some functionalized oxetanes., Ministerio de Ciencia e Innovación and FEDER (CTQ2016-75023-C2-1-P), and Junta de Castilla y León and FEDER (BU291P18, BU049P20). The project leading to these results has also received funding from the “la Caixa” Foundation, under agreement LCF/PR/PR18/51130007) (CAIXA-UBU001). A postdoctoral contract (S.S.-P.) and a predoctoral contract (C.S.) were funded by Junta de Castilla y León and FEDER and Ministerio de Educación (FPU), respectively

The synthesis of nitrogen-containing heterocycles, including natural alkaloids and other compounds presenting different types of biological activities have proved to be successful employing chiral sulfinyl imines derived from tert-butanesulfinamide. These imines are versatile chiral auxiliaries and have been extensively used as eletrophiles in a wide range of reactions. The electron-withdrawing sulfinyl group facilitates the nucleophilic addition of organometallic compounds to the iminic carbon with high diastereoisomeric excess and the free amines obtained after an easy removal of the tert-butanesulfinyl group can be transformed into enantioenriched nitrogen-containing heterocycles. The goal of this review is to the highlight enantioselective syntheses of heterocycles involving the use of chiral N-tert-butanesulfinyl imines as reaction intermediates, including the synthesis of several natural products. The synthesis of nitrogen-containing heterocycles in which the nitrogen atom is not provided by the chiral imine will not be considered in this review. The sections are organized according to the size of the heterocycles. The present work will comprehensively cover the most pertinent contributions to this research area from 2012 to 2020. We regret in advance that some contributions are excluded in order to maintain a concise format. We thank the continuous financial support from the Spanish Ministerio de Economía y Competitividad (MINECO; project CTQ2014-53695-P, CTQ2014-51912-REDC, CTQ2016-81797-REDC, CTQ2017-85093-P), Ministerio de Ciencia, Innovación y Universidades (RED2018-102387-T, PID2019-107268GB-100), FEDER, the Generalitat Valenciana (PROMETEOII/2014/017), and the University of Alicante (VIGROB-068). We are also grateful for the financial support from Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES).

Nitroenynes are an interesting electrophile in asymmetric organocatalysis, due to the versatility of the functional groups present in its structure. This review covers the organocatalytic examples using this electrophile and its application for the synthesis of chiral heterocycles.

Solid-state photovoltaic cells based on robust metal-organic frameworks (MOFs), MIL-125(Ti), MIL-125(Ti)-NH, UiO-67, Ru(bpy)-UiO-67, (bpy 2,2‘-bipyridine) as active components and spiro-MeOTAD (MeOTAD 2,2‘,7,7‘-tetrakis[N,N-di(p-methoxyphenyl)amino]-9,9′-spirobifluorene) as hole transporting layer have been prepared., The photovoltaic response of this material increases in the presence of bathochromic −NH groups on the linker or Ru (II) polypyridyl complexes light harvester. These results show that the strategies typically employed in photocatalysis to enhance the photocatalytic activity of MOFs can also be applied in the field of photovoltaic devices., Financial support by the Spanish Ministry of Science and Innovation (Severo Ochoa and RTI2018-98276-CO2-1) and Generalitat Valenciana (Prometeo 2017/083) is gratefully acknowl-edged. S.N. thanks financial support by the Ministerio de Ciencia, Innovación y Universidades (RTI 2018–099482-A−I00 project) and Agencia Valenciana de la Innovación (AVI-GVA, Carboagua project, INNEST/2020/111).

51 p.-6 fig.-1 tab.-4 schem.-1 graph. abst., Bacterial resistance to antibiotics makes previously manageable infections again disabling and lethal, highlighting the need for new antibacterial strategies. In this regard, inhibition of the bacterial division process by targeting key protein FtsZ has been recognized as an attractive approach for discovering new antibiotics. Binding of small molecules to the cleft between the N-terminal guanosine triphosphate (GTP)-binding and the C-terminal subdomains allosterically impairs the FtsZ function, eventually inhibiting bacterial division. Nonetheless, the lack of appropriate chemical tools to develop a binding screen against this site has hampered the discovery of FtsZ antibacterial inhibitors. Herein, we describe the first competitive binding assay to identify FtsZ allosteric ligands interacting with the interdomain cleft, based on the use of specific high-affinity fluorescent probes. This novel assay, together with phenotypic profiling and X-ray crystallographic insights, enables the identification and characterization of FtsZ inhibitors of bacterial division aiming at the discovery of more effective antibacterials., Thiswork was supported by grants BFU 2014-51823-R (J.M.A.),SAF2016-78792-R, PID2019-106279RB-I00 (M.L.L.-R.), BFU2017-87387-P (C.F.-T.), and predoctoral FPU fellowshipsfrom MECD (A.E.-P. and M.A.).

The development of new techniques for the preparation of organic compounds is important, with catalytic processes being key to this innovation. The development of copper-based metal-organic frameworks to promote oxidative couplings has allowed the synthesis of amides in a very effective manner. This methodology has been successfully applied to the unique preparation of the bioactive compound N,N-diethyl-3-methylbenzamide, with excellent performance (>99% conversion and 95% yield of pure isolated product) on a preparative scale. The described procedure can be classified as an excellent synthesis (EcoScale) considering environmental and economic factors based on different “green metrics” (atom economy, reaction mass efficiency, materials recovery factor, stoichiometric factor, E-factor). This research was funded by Ministerio de Ciencia, Innovación y Universidades (grant number PGC2018-096616-B-I00), Ministerio de Educación, Cultura y Deporte (grant number FPU15/06040), Generalitat Valenciana (grant number AICO/2021/013) and the University of Alicante (grant number VIGROB-316).

Glucose oxidase (GOX) and catalase (CAT) regulate the amount of H2O2 in honey, by generating or consuming it, so they are related to the antibacterial and antioxidant activity of honey. However, their activities are hardly analysed, since the process requires a previous dialysis that is non-selective, very time-consuming (>24 h), eco-unfriendly (>6L of buffer) and expensive. This research shows the design and performance of a material that selectively removes the actual interferents. The film-shaped-polymer is immersed for 90́ within a honey solution (12.5 mL of buffer), where it interacts exclusively with 1,2-dihydroxybenzenes, which we proved to be the real interferents (the material contains motifs derived from phenylboronic acid to interact with 1,2-diols). Polymeric chains favour condensation to occur exclusively with 1,2-dihydroxybenzenes, excluding monosaccharides. The interferents’ removal using our designed polymer is selective, low cost (1.42€ per test), rapid and eco-friendly (saves 6L of buffer and 20.5 h of experimental workout per sample)., We gratefully acknowledge the financial support provided by all funders. Author Jose Miguel García received grant PID2020-113264RB-I00 / AEI / 10.13039/501100011033 funded by MCIN/AEI/ 10.13039/501100011033 and by “ERDF A way of making Europe”. Ana Arnaiz received funding from Ministerio de Universidades-European Union in the frame of NextGenerationEU RD 289/2021 (Universidad Politécnica de Madrid). We also gratefully acknowledge European Regional Development Fund (ERDF). Gianluca Utzeri thanks Fundação para a Ciência e a Tecnologia (FCT, Portugal) for PhD grant (SFR/BD/146358/2019). The Coimbra Chemistry Centre is supported by the FCT, through Projects UIDB/00313/2020 and UIDP/00313/2020. To all the beekeepers who provided a sample of honey for this study.

The ambiguous bonding situation of σ-E−H (E=Si, B) complexes in transition metal compounds has been rationalized by means of Density Functional Theory calculations. To this end, the combination of the Energy Decomposition Analysis (EDA) method and its Natural Orbital for Chemical Valance (NOCV) extension has been applied to representative complexes described in the literature where the possible η1 versus η2 coordination mode is not unambiguously defined. Our quantitative analyses, which complement previous data based on the application of the Quantum Theory of Atoms in Molecules (QTAIM) approach, indicate that there exists a continuum between genuine η1 and η2 modes depending mainly on the strength of the backdonation. Finally, we also applied this EDA-NOCV approach to related main-group species where the backdonation is minimal.

In this work, [Fe3O4@SiO2(CH2)3][DABCO-H][C(CN)3]2 was prepared, identified by various analyses such as FT-IR, EDX, SEM coupled EDX (SEM mapping), XRD, FE-SEM, TEM, TGA, DTG, ICP and VSM and used as a nanomagnetic catalyst for the synthesis of henna-based benzopyrazolo[3,4-b]quinolindiones via cooperative vinylogous anomeric based oxidation under solvent-free condition. Some of these products are new and reported for the first time. We thank the Bu-Ali Sina University, the Hamedan University of Technology, and Iran National Science Foundation [(INSF), Grant Number: 98001912) for financial support to our research group.

Esta tesis doctoral se ha desarrollado en los laboratorios del Departamento de Ingeniería Química y de Materiales de la Facultad de Ciencias Químicas de la Universidad Complutense de Madrid. La actividad investigadora se ha llevado a cabo en el seno del grupo de investigación consolidado “Desarrollo de Procesos y Productos de Bajo Impacto Ambiental”. Los directores de la tesis doctoral han sido los profesores D. Francisco Rodríguez Somolinos y D. Julián García González, catedrático y profesor titular, respectivamente, del Departamento de Ingeniería Química y de Materiales. La tesis doctoral se ha financiado a través de los proyectosCTQ2017-85340-R del Ministerio de Economía, Industria y Competitividad (MINECO) y P2018/EMT-4348 (SUSTEC) de la Comunidad de Madrid. Además, el doctorando ha disfrutado de una beca de Formación de Personal Investigador (FPI) con referenciaPRE2018-083728 al amparo del proyecto de investigación CTQ2017-85340-R...

The extensive use of graphene materials in real-world applications has increased their potential release into the environment. To evaluate their possible health and ecological risks, there is a need for analytical methods that can quantify these materials at very low concentrations in environmental media such as water. In this work, a simple, reproducible, and sensitive method to detect graphene oxide (GO) in water samples using the surface-enhanced Raman spectroscopy (SERS) technique is presented. The Raman signal of graphene is enhanced when deposited on a substrate of gold nanoparticles (AuNPs), thus enabling its determination at low concentrations with no need for any preconcentration step. The practical limit of quantification achieved with the proposed method was 0.1 ng mL–1, which is lower than the predicted concentrations for graphene in effluent water reported to date. The optimized procedure has been successively applied to the determination of ultratraces of GO in water samples.

Bimetallic Fe–Cu MOF was effectively synthesized through a one-pot solvothermal process and successfully characterized by TEM, XPS, SEM, XRD, BET, EDX, elemental mapping, and FT-IR analysis. This bimetallic MOF was employed as a catalyst in the reduction of nitroarenes at room temperature and as well as in the reduction of dyes, for example, methyl orange (MO) and methylene blue (MB). Results pointed to Fe–Cu MOF exhibiting outstanding catalytic performance for both room temperature reactions. The catalytic activity of Fe–Cu MOF in comparison with Fe-MOF and Cu-MOF in the nitroarenes reduction indicated a superior activity compared with single-metal MOFs. Activity of Fe–Cu MOF catalyst did not change after its recycling and reusing for seven consecutive cycles in nitrobenzene reduction. The authors are grateful to Institute for Advanced Studies in Basic Sciences (IASBS) Research Council and Iran National Science Foundation (INSF-Grant number of 97016837). This publication has also been supported by RUDN University Strategic Academic Leadership Program (R. Luque). We also gratefully acknowledge financial support from the Spanish Ministerio de Ciencia, Innovación y Universidades (projects CTQ2016-81893REDT and RED2018-102387-T), the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P, CTQ2016-80375-P, CTQ2017-82935-P and PID2019-107268GB-I00), Generalitat Valenciana (IDIFEDER/2021/013) and the University of Alicante.

[EN] The role of desensitization in mating disruption (MD) of European Grapevine Moth (EGVM), Lobesia botrana (Dennis and Schiffermüller) (Lepidoptera: Tortricidae), is studied by exposing males to different airborne pheromone concentrations for various time intervals prior to evaluate their behavioural response. By using different types of dispensers, male moths are exposed to three decreasing pheromone concentrations (up to the minimum concentration able to desensitize them) for 1, 3, and 24¿h. The airborne pheromone concentration present in all treatments is accurately quantified using gas chromatography¿mass spectrometry equipment to compare these data with actual airborne pheromone concentrations under field conditions. The effect of pheromone exposure on L. botrana males is studied in wind tunnel and electroantennogram assays, immediately and 24¿h after the exposure period. Results show that the reduction of response to the pheromone depended on the dose and the duration of the treatment, but the lowest dose tested did not produce desensitization. These results support that the most important mechanisms of MD acting in fields treated against EGVM are the competitive ones and that the non-competitive ones only may become relevant very close to pheromone dispensers. Our results support the hypothesis of cross-adaptation to other chemical stimuli in the pre-exposed moths to their pheromone although more studies are needed to draw stronger conclusions., This work was supported by Conselleria de Agricultura, Medio Ambiente, Cambio Climático y Desarrollo Rural (Generalitat Valenciana) under grant agreement S8456000. The authors would like to thank Ana Castellar for language editing

Tesis (Doctora en Ciencias Químicas) - - Universidad Nacional de Córdoba. Facultad de Ciencias Químicas, 2022 Resumen: Las transformaciones orgánicas a través de procesos iniciados por la luz visible surgen como estrategias que satisfacen la creciente demanda de procesos químicos mas sostenibles. Y esto es particularmente importante no sólo en la química orgánica sino también en términos de la aceptación social de las reacciones llevadas a cabo a escala industrial. La aplicación de la luz en las reacciones orgánicas involucra el uso de metodologías sintéticas más limpias en comparación con las reacciones de calentamiento convencionales: simplifica la purificación del producto, no genera residuos y puede obtenerse a partir de fuentes renovables. En este trabajo de tesis se desarrollan nuevas metodologías sintéticas que implican el uso de la luz visible aplicada a la síntesis, la transformación y la modificación de moléculas orgánicas de interés. En una primera parte, reacciones de N-desulfonilación y deshalogenación son iniciadas por la luz visible y llevadas a cabo libres de metales de transición, a temperatura ambiente y en tiempos cortos de reacción. Los siguientes dos capítulos implican el uso de la luz visible para, en este caso, la síntesis de una gran familia de 6H-benzo[c]cromenos, 9H-carbazoles y fenantridin-6(5H)-onas a partir de una arilación intramolecular C-H. Finalmente, en el último capítulo, se estudian fotocatalizadores de TiO2 conteniendo distintas proporciones de anatasa y rutilo en la reacción de homoacoplamiento de Ullmann para la síntesis de bifenilos iniciada por luz visible. 2024-05-31 Fil: Heredia, Micaela Denise. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas; Argentina.

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior O fungo biotrófico Hemileia vastatrix é um parasita obrigatório das folhas vivas do gênero Coffea. Este fungo causa uma doença devastadora na cultura do café, conhecida como ferrugem do café, que se não controlada previamente, implica em perdas acentuadas na produção. O método químico, através do uso de fungicidas, é o mais eficiente e amplamente utilizado para controle deste patógeno. Há evidências crescentes de danos ao meio ambiente decorrentes do uso contínuo de muitos pesticidas disponíveis no mercado. A pressão causada pelo uso repetitivo destes compostos, tem levado, para alguns desses produtos, à seleção de populações de pragas resistentes a esses. Há, então, uma crescente necessidade de desenvolvimento de novos fungicidas, eficientes e ambientalmente seguros. Os metabólitos secundários produzidos por plantas e micróbios possuem amplos campos de aplicação na indústria farmacêutica, de cosméticos, alimentos e agroquímicos. Dentre os últimos, destacam-se os fungos. Esses são capazes de produzir compostos bioativos que podem servir de base para a descoberta e desenvolvimento de novos produtos de interesse para aplicações industriais e agrícolas. Um estudo prévio relatou a descoberta de uma nova espécie de fungo do gênero Calonectria – Calonectria hemileiae, encontrado atuando como micoparasita de H. vastatrix. Neste estudo, foi verificado que C. hemileiae tem bom potencial para uso como agente de controle biológico de H. vastatrix. Porém, verificou-se que o mesmo também é patógeno do eucalipto e outras espécies de plantas, o que imporia limitações ao seu uso como ferramenta para o controle biológico da ferrugem do cafeeiro. No presente trabalho foi, preliminarmente, avaliada a atividade antifúngica de filtrados e extratos orgânicos obtidos do filtrado de cultura de C. hemileiae, contra H. vastatrix e identificados os constituintes químicos presentes nestes extratos, na busca por metabólitos produzidos pelo fungo e que possam apresentar potencial como fungicidas naturais para o controle de H. vastatrix. Os extratos do filtrado de cultura foram obtidos através de extrações líquido-líquido sucessivas utilizando os solventes hexano, diclorometano e acetato de etila. As atividades antifúngicas dos extratos contra H. vastatrix foram avaliadas e comparadas estatisticamente pelo teste de Scott Knott em significância de 0,05. Curvas de dose-resposta foram construídas paras os extratos e os valores IC 50 foram obtidos. Os extratos foram submetidos a análise por CG-EM. Assim como o controle positivo, os três extratos inibiram completamente a germinação de urediniospóros de H. vastatrix na concentração de 500 µg ml -1 . Os valores de IC 50 obtidos para os extratos em hexano, diclorometano e acetato de etila foram de 153,3 ± 9,6, 202,6 ± 15,0 e 186,6 ± 6,0 µg ml -1 , enquanto que para o controle positivo foi de 5,3 ± 0,5 µg ml -1 . A partir da análise por CG-EM foi possível a identificação de sete compostos no extrato em hexano (5,37%), cinco no extrato em diclorometano (4,16%) e um total de quarenta e oito no extrato em acetato de etila, sendo trinta e três no extrato derivatizado (56,73%) e trinta e dois no extrato hidrolisado-derivatizado (47,78%), sendo dezessete presentes em ambos os extratos. Apesar dos valores de IC 50 obtidos para os três extratos serem superiores ao do controle positivo, os três apresentaram atividade antifúngica promissora. Muitos relatos na literatura confirmam o potencial antifúngico de alguns compostos presentes nos extratos, pertencentes as classes dos terpenos, ácidos graxos, álcoois, ácidos carboxílicos e hidroxiácidos. Palavras-chave: Biofungicidas. Fungicidas naturais. Café. Ferrugem-do-café. Atividade antifúngica. The biotrophic fungus Hemileia vastatrix is an obligate parasite of live leaves of the genus Coffea. This fungus causes a devastating disease in coffee culture, known as coffee rust, which, if not previously controlled, implies severe losses in production. The chemical method, through the use of fungicides, is the most efficient and widely used to control this pathogen. There is growing evidence of damage to the environment from the continued use of many commercially available pesticides. The pressure caused by the repetitive use of these compounds has led, for some of these products, to the selection of pest populations resistant to them. There is, therefore, a growing need to develop new, efficient and environmentally safe fungicides. Secondary metabolites produced by plants and microbes have wide application fields in the pharmaceutical, cosmetic, food and agrochemical industries. Among the latter, fungi stand out. These are capable of producing bioactive compounds that can serve as a basis for the discovery and development of new products of interest for industrial and agricultural applications. A previous study reported the discovery of a new species of fungus of the genus Calonectria – Calonectria hemileiae, found acting as a mycoparasite of H. vastatrix. In this study, it was verified that C. hemileiae has good potential for use as a biological control agent for H. vastatrix. However, it was found that it is also a pathogen of eucalyptus and other plant species, which would impose limitations on its use as a tool for the biological control of coffee rust. In the present work, it was preliminarily evaluated the antifungal activity of filtrates and organic extracts obtained from the culture filtrate of C. hemileiae, against H. vastatrix and identified the chemical constituents present in these extracts, in the search for metabolites produced by the fungus and that may present potential as natural fungicides for the control of H. vastatrix. Extracts from the culture filtrate were obtained through successive liquid- liquid extractions using the solvents hexane, dichloromethane and ethyl acetate. The antifungal activities of the extracts against H. vastatrix were evaluated and statistically compared using the Scott Knott test at a significance level of 0.05. Dose-response curves were constructed for the extracts and IC50 values were obtained. The extracts were analyzed by GC-MS. As well as the positive control, the three extracts completely inhibited the germination of urediniospores of H. vastatrix at a concentration of 500 µg ml-1. The IC50 values obtained for the extracts in hexane, dichloromethane and ethyl acetate were 153.3 ± 9.6, 202.6 ± 15.0 and 186.6 ± 6.0 µg ml-1, while for the positive control was 5.3 ± 0.5 µg ml-1. From the analysis by GC-MS, it was possible to identify seven compounds in the hexane extract (5.37%), five in the dichloromethane extract (4.16%) and a total of forty-eight in the ethyl acetate extract. , being thirty-three in the derivatized extract (56.73%) and thirty-two in the hydrolyzed-derivatized extract (47.78%), being seventeen present in both extracts. Despite the IC50 values obtained for the three extracts being higher than the positive control, all three showed promising antifungal activity. Many reports in the literature confirm the antifungal potential of some compounds present in the extracts, belonging to the classes of terpenes, fatty acids, alcohols, carboxylic acids and hydroxy acids. Keywords: Biofungicides. Natural fungicides. Coffee. Coffee leaf rust. Antifungal activity.

Overcoming resistance is one of the most challenging features in current anticancer therapy. Autophagy is a cellular process that confers resistance in some advanced tumors, since it enables cancer cells to adapt to stressful situations, such as anticancer treatments. Hence, the inhibition of this cytoprotective autophagy leads to tumor cells sensitization and death. In this regard, we designed a novel potent anionophore compound that specifically targets lysosomes, called LAI-1 (late-stage autophagy inhibitor-1), and evaluated its role in blocking autophagy and its potential anticancer effects in three lung cancer cell lines from different histological subtypes. Compared to other autophagy inhibitors, such as chloroquine and 3-Methyladenine, the LAI-1 treatment induced more potent anticancer effects in all tested cancer cells. LAI-1 was able to efficiently target and deacidify lysosomes, while acidifying cytoplasmic pH. Consequently, LAI-1 efficiently blocked autophagy, indicated by the increased LC3-II/I ratio and p62/SQSTM1 levels. Moreover, no colocalization was observed between autophagosomes, marked with LC3 or p62/SQSTM1, and lysosomes, stained with LAMP-1, after the LAI-1 treatment, indicating the blockage of autophagolysosome formation. Furthermore, LAI-1 induced cell death by activating apoptosis (enhancing the cleavage of caspase-3 and PARP) or necrosis, depending on the cancer cell line. Finally, LAI-1 sensitized cancer cells to the first-line chemotherapeutic agent cisplatin. Altogether, LAI-1 is a new late-stage autophagy inhibitor that causes lysosomal dysfunction and the blockage of autophagolysosome formation, as well as potently induces cancer cell death and sensitization to conventional treatments at lower concentrations than other known autophagy inhibitors, appearing as a potential new therapeutic approach to overcome cancer resistance., This research was supported by Consejería de Educación de la Junta de Castilla y León (grant BU067P20), MCIN/AEI/10.13039/501100011033 (grant PID2020-117610RB-I00) and Instituto de Salud Carlos III (grant PI18/00441), co-funded by the European Regional Development Fund. ERDF, a way to build Europe. P.F., D.A.-C. and I.C.-B. thank Consejería de Educación de la Junta de Castilla y León, European Social Fund and ERDF for their predoctoral (D.A.-C.) and postdoctoral (P.F. and I.C.-B.) contracts. C.B.-G. thanks the University of Barcelona for a predoctoral fellowship.

CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico Plantas pertencentes à família Celastraceae são consideradas como fontes promissoras de compostos bioativos, destacando-se os triterpenos pentacíclicos (TPs). Neste contexto, este trabalho teve como objetivo realizar um levantamento bibliográfico dos triterpenos pentacíclicos isolados de plantas da família Celastraceae entre os anos 2001 e 2021, realizar um estudo fitoquímico das folhas de Pristimera celastroides e das folhas e raízes de Fraunhofera multiflora e obter e caracterizar quimicamente óleos essenciais de diferentes partes e espécies dessa família. Os resultados obtidos foram apresentados em três capítulos. No Capítulo 1 foi descrito o levantamento bibliográfico, sendo relatados 504 triterpenos pentacíclicos isolados de espécies de Celastraceae entre os anos 2001 e 2021. Esses foram classificados como friedelanos (103), quinonametídeos (22), aromáticos (29), dímeros (50), lupanos (89), oleananos (102), ursanos (88) e outros (21). No capítulo 2 foram discutidos os resultados dos estudos fitoquímicos das espécies P. celastroides e F. multiflora. Da espécie P. celastroides foram isolados e identificados uma mistura de hidrocarbonetos (PC-1) e de ácidos carboxílicos (PC-3 e PC-6), dois compostos esterificados pertencentes a classe dos cicloartanos [3β-aciloxi-9,19-ciclolanost-24-eno (PC-4) e 3β-aciloxi-9,19-ciclolanostan-24,21-diol (PC-10)], o β-sitosterol na sua forma esterificada (3β-aciloxi-sitosterol, PC-8) e livre (PC-9), o esqualeno (PC-2), o polímero guta-percha (PC-5) e a vitamina E (α-tocoferol, PC-7). Por sua vez, o estudo fitoquímico das folhas e raízes de F. multiflora resultou no isolamento de três misturas de hidrocarbonetos (FM-1a, FM-1b e FM-1c) e duas misturas constituídas por isômeros da classe dos ursanos e oleananos: olean-12-en-3β,11α-diol (FM-8) + ursan-12-en-3β,11α-diol (FM-9) e ursan-11,12(13)-dien-3β-ol (FM-15) + olean-11,12(13)-dien-3β-ol (FM-16). Foram isolados TPs da classe dos friedelanos (friedelina, FM-2, e friedelinol, FM-14), ursanos (α-amirina, FM-4, e ácido ursólico, FM-7), oleananos (olean-11,13(18)-dien-3β-ol, FM-6) e quinonametídeos (pristimerina, FM-13). Além desses, foram isolados também o polímero guta-percha (FM-3), dois esteroides (β-sitosterol, FM-5, e 3-O-β-D-(6-O-aciloxi-glicosil)-β-sitosterol, FM-11) e misturas compostas por alcaloides macrocíclicos derivados da espermidina (FM-12a, FM-12b e FM-12c). Por fim, no capítulo 3 foi descrito um estudo comparativo da composição química de óleos essenciais extraídos de espécies de Celastraceae. Foram obtidos 17 óleos essenciais a partir de diferentes partes de nove espécies de Celastraceae, nos quais foram identificados por CG-EM um total de 130 constituintes diferentes. Os compostos comuns na maioria dos óleos essenciais foram os isômeros cis e trans-óxido de linalol, nerilacetona, linalol, β-ionona, α-ionona, nerolidol, decanal e ácido dodecanoico. Por meio da análise de componentes principais (PCA) verificou-se um perfil de similaridade na composição química dos óleos essenciais das espécies vegetais estudadas. Foram avaliadas as atividades antimicrobiana e inibitória da enzima cetilcolinesterase, nas quais os óleos essenciais apresentaram baixa ou nenhuma inibição. Os dados relatados nos três capítulos destacam a abundância e a diversidade estrutural de TPs isolados de espécies de Celastraceae, bem como os resultados obtidos no estudo dos óleos essenciais podem ser utilizados como referência para a realização de estudos quimiotaxonômicos. lants belonging to the Celastraceae family are considered as promising sources of bioactive compounds, especially pentacyclic triterpenes (TPs). This work aimed to carry out a bibliographic survey of pentacyclic triterpenes isolated from Celastraceae plants between the years 2001 and 2021, a phytochemical study of the leaves of Pristimera celastroides and leaves and roots of Fraunhofera multiflora and to obtain and chemically characterize essential oils from different parts and species of this family. The results obtained were presented in three chapters. In Chapter 1, the bibliographic survey was described, and 504 pentacyclic triterpenes isolated from Celastraceae species were reported between 2001 and 2021. These were classified as friedelanes (103), quinonamethides (22), aromatics (29), dimers (50), lupanes (89), oleananes (102), ursanes (88) and others (21). In chapter 2, the results of phytochemical studies of the species P. celastroides (leaves) and F. multiflora (leaves and roots) were discussed. From the species P. celastroides, a mixture of hydrocarbons (PC-1) and carboxylic acids (PC-3 and PC-6), two esterified compounds belonging to the class of cycloarthanes [3β-acyloxy-9,19-cyclolanostan-24-ene (PC-4) and 3β-acyloxy-9,19-cyclolanostan-24,21-diol (PC-10)], β-sitosterol in its esterified form (3β-acyloxy-sitosterol, PC-8) and free form (PC-9), squalene (PC-2), gutta-percha polymer (PC-5) and vitamin E (α-tocopherol, PC-7). The phytochemical study of F. multiflora resulted in the isolation of three mixtures of hydrocarbons (FM-1a, FM-1b and FM-1c) and two mixtures composed of isomers of the class of ursanes and oleananes: olean-12-en-3,11α-diol (FM-8) + ursan-12-en-3β,11α-diol (FM-9) e ursan-11,12(13)-dien-3β-ol (FM-15) + olean-11,12(13)-dien-3β-ol (FM-16). TPs of the following types were isolated: friedelanes (friedelin, FM-2, and friedelinol, FM-14), ursanes (α-amyrin, FM-4, and ursolic acid, FM-7), oleananes (olean-11,13(18)-dien-3β-ol, FM-6) and quinonamethides (pristimerin, FM-13). In addition to these, the polymer gutta-percha (FM-3), two steroids (β sitosterol, FM-5, and 3-O-β-D-(6-O-acyloxy-glycosyl)-β-sitosterol, FM-11) and mixtures composed of macrocyclic alkaloids derived from spermidine (FM-12a, FM-12b and FM-12c) were isolated. Finally, in chapter 3, a comparative study of the chemical composition of essential oils extracted from species of Celastraceae was described. Seventeen essential oils were obtained from different parts of nine species of Celastraceae. A total of 130 different constituents were identified by GC-EM, among which the cis and trans-oxide isomers of linalool, nerylacetone, linalool, β-ionone, α-ionone, nerolidol, decanal and dodecanoic acid, detected in most essential oils. The principal component analysis showed a similarity profile in the chemical composition of the essential oils of the studied plant species. The antimicrobial and anticholinesterase activities were evaluated, in which the essential oils showed low or no inhibition. The data reported in the three chapters highlight the abundance and structural diversity of TPs isolated from Celastraceae species, as well as the results obtained in the study of essential oils can be used as a reference for carrying out chemotaxonomic studies.

Resumen La química orgánica es el pilar de muchas disciplinas entre las cuales se encuentran la farmacia, la síntesis orgánica, la industria de alimentos, la biotecnología y la microbiología [1, 2]. El posgrado en Ciencias (Microbiología) del Instituto de Ciencias de la Benemérita Universidad Autónoma de Puebla (ICUAP), oferta un curso propedéutico desde hace ya varios años, con el fin de apoyar a los estudiantes a recordar cuestiones clave en varias materias incluyendo: química, fisicoquímica, microbiología general, biología molecular, bioquímica y biología celular [3]. Dentro de la química, una sección importante es la química orgánica, en la cual se hace un recordatorio de la química de carbono, la estructura de alcanos, alquenos y alquinos en función de la configuración electrónica del carbono [4, 5]. También se revisan los principales grupos funcionales [6] y se hace un recordatorio de la química estructural y los enantiómeros [7]. Se muestran formas de representar moléculas y se hace un recordatorio sobre la forma de nombrar a los compuestos orgánicos (nomenclatura). A continuación, se muestra una video conferencia que relata estos temas de forma breve., {"references":["Kothari D, Hall AO, Castañeda CA, McNeil AJ. Connecting Organic Chemistry Concepts with Real-World Contexts by Creating Infographics. J Chem Educ [Internet]. 2019 Nov 12;96(11):2524–7. Available from: https://doi.org/10.1021/acs.jchemed.9b00605","Rushton GT, Hardy RC, Gwaltney KP, Lewis SE. Alternative conceptions of organic chemistry topics among fourth year chemistry students. Chem Educ Res Pract [Internet]. 2008;9(2):122–30. Available from: http://dx.doi.org/10.1039/B806228P","ICUAP. Posgrado en Ciencias (Microbiología) [Internet]. BUAP. Available from: https://icuap.buap.mx/posgrado-en-ciencias-microbiológicas","Tascón JMD. Materiales de carbono: estructuras y formas. 2007. Microsoft Word - 1706_FINAL.doc (csic.es)","Román Carracedo D. La química del Carbono como unidad didáctica [Internet]. Available from: http://uvadoc.uva.es/handle/10324/31202","Velásquez Márquez A. Principales grupos funcionales en química orgánica [Internet]. UNAM; p. 1–8. Available from: https://dcb.ingenieria.unam.mx/wp-content/themes/tempera-child/CoordinacionesAcademicas/FQ/Q/Articulos/a_Principales Grupos Funcionales en QO.pdf","Mislow K, Siegel J. Stereoisomerism and local chirality. J Am Chem Soc [Internet]. 1984 May 1;106(11):3319–28. Available from: https://doi.org/10.1021/ja00323a043"]}

[EN] Passive dispensers are the most widely used dispensers to control the European grapevine moth, Lobesia botrana (Denis & Schiffermüller) (Lepidoptera: Tortricidae), by mating disruption (MD). Although their efficacy is well-proven, efforts are needed to reduce the use of pheromone without compromising efficacy and to allow lower MD costs. For this purpose, two different widely employed dispenser types in Europe against this pest (Ampoule and Rope dispensers) were evaluated in the field to verify their performance (emission rates and efficacy) in relation to weather conditions. Their release profiles were studied by extracting and quantifying the residual pheromone load over time by gas chromatography. Dispensers' performance in relation to weather conditions was then assessed by correlating the daily emission rates with the mean daily values of several of these variables. Although both dispenser types were efficient in controlling L. botrana populations and reducing fruit damage, their pheromone content and their release rates differed at the end of the crop cycle. The Ampoule dispensers emitted lower amounts of pheromone throughout the study period, whereas the Rope dispensers¿ emissions were weather-dependent, with higher emission rates at higher mean temperatures and wind speeds. Our results showed that the current commercial MD dispensers could be improved by adjusting their release rates to better reflect actual pheromone requirements., Authors would like to thank Celler del Roure winery (Mogente, Valencia) and Emilio Giménez (Venta del Moro) for providing field study vineyards. This research received funding from Conselleria de Agricultura, Desarrollo Rural, Emergencia Climática y Transicion Ecologica (Generalitat Valenciana) under grant agreement S8456000. We are also grateful to Ana Castellar and Helen Warburton for language editing. Funding for open access charge: CRUE-Universitat Politécnica de Valéncia.

Although it is well-known that nitroaromatic compounds quench the fluorescence of different conjugated polymers and form colored Meisenheimer complexes with proper nucleophiles, the potential of paper as a substrate for those macromolecules can be further developed. This work undertakes this task, impregnating paper strips with a fluorene-phenylene copolymer with quaternary ammonium groups, a bisfluorene-based cationic polyelectrolyte, and poly(2-(dimethylamino)ethyl methacrylate) (polyDMAEMA). Cationic groups make the aforementioned polyfluorenes attachable to paper, whose surface possesses a slightly negative charge and avoid interference from cationic quenchers. While conjugated polymers had their fluorescence quenched with nitroaromatic vapors in a non-selective way, polyDMAEMA-coated papers had a visual response that was selective to 2,4,6-trinitrotoluene (TNT), and that could be easily identified, and even quantified, under natural light. Far from implying that polyfluorenes should be ruled out, it must be taken into account that TNT-filled mines emit vapors from 2,4-dinitrotoluene (DNT) and dinitrobenzene isomers, which are more volatile than TNT itself. Atmospheres with only 790 ppbv TNT or 277 ppbv DNT were enough to trigger a distinguishable response, although the requirement for certain exposure times is an important limitation., This work was carried out under the Project inpactus—innovative products and technologies from eucalyptus, Project No. 21874 funded by Portugal 2020 through European Regional Development Fund (ERDF) in the frame of COMPETE 2020 No. 246/AXIS II/2017. Finantial support from the Coimbra Chemistry Centre (CQC), which is supported by the Fundação para a Ciência e a Tecnologia (FCT) through the programs UID/QUI/00313/2020 and COMPETE is gratefully acknowledged.

Hydroxytyrosol (HT) and punicalagin (PC) exert cardioprotective and antiatherosclerotic effects. This study evaluated the effect of an oral supplement containing HT and PC (SAx) on dyslipidemia in an adult population. A randomized, double-blind, controlled, crossover trial was conducted over a 20-week period. SAx significantly reduced the plasma levels of triglycerides (TG) in subjects with hypertriglyceridemia (≥150 mg/dL) (from 200.67 ± 51.38 to 155.33 ± 42.44 mg/dL; p < 0.05), while no such effects were observed in these subjects after the placebo. SAx also significantly decreased the plasma levels of low-density lipoprotein cholesterol (LDL-C) in subjects with high plasma levels of LDL-C (≥160 mg/dL) (from 179.13 ± 16.18 to 162.93 ± 27.05 mg/dL; p < 0.01), while no such positive effect was observed with the placebo. In addition, the placebo significantly reduced the plasma levels of high-density lipoprotein cholesterol (HDL-C) in the total population (from 64.49 ± 12.65 to 62.55 ± 11.57 mg/dL; p < 0.05), while SAx significantly increased the plasma levels of HDL-C in subjects with low plasma levels of HDL-C (

[ES] La presente tesis doctoral ha centrado la atención en la síntesis de nuevos materiales MOFs obtenidos por intercambio post-sintético de MOFs descritos anteriormente o por heterounión de MOFs estables que tienen estructura UiO66. Estos materiales se han aplicado como fotocatalizadores para la prometedora reacción de división completa del agua que pretende obtener H2 y O2 en forma estequiométrica a partir de agua en ausencia de agentes sacrificantes o nanopartículas metálicas. El nuevo material UiO66 (Zr/Ce/Ti) mostró resultados sorprendentes para la reacción general de división del agua en ambas condiciones de luz UV-Visible e irradiación solar. También se obtuvieron resultados interesantes en el caso del nucleo-corteza UiO66(Zr)-NH225@UiO66(Ce) que, en presencia de agua, cuando se irradió con luz ultravioleta y con luz solar, permitió obtener 550 𝝁 mol*g- 1 de H2 y 350 𝝁 mol*g-1 de H2 en 24 h respectivamente, en las mismas condiciones de trabajo definidas para UiO66(Zr/Ce/Ti). En este trabajo de tesis se presentó por primera vez la posibilidad de reducir 4-NP a través de una metodología tándem que involucra primero la producción de H2 a partir de agua en presencia de metanol, como agente de sacrificio, y UiO66(Zr)-NH2, como fotocatalizador, y la posterior reducción de 4-NP a 4-AP. Por otro lado, se ha demostrado que los materiales defectuosos con estructura de UiO66 pueden reducir selectivamente los dobles enlaces polarizados X=Y en presencia de gas H2., [CA] La present tesi doctoral ha centrat l'atenció en la síntesi de nous materials MOFs obtinguts per intercanvi post-sintètic de MOFs descrits anteriorment o per heterounió de MOFs estables que tenen estructura UiO66. Estos materials s'han aplicat com fotocatalitzadors per a la prometedora reacció de divisió completa de l'aigua que pretén obtindre H2 i O2 en forma estequiomètrica a partir d'aigua en absència d'agents sacrificants o nanopartícules metàl·liques. El nou material UiO66 (Zr/Ce/Ti) va mostrar resultats sorprenents per a la reacció general de divisió de l'aigua en ambdós condicions de llum UV-Visible i irradiació solar. També es van obtindre resultats interessants en el cas del core-shell UiO66 (Zr) - NH225@UiO66 (Ce) que, en presència d'aigua, quan es va irradiar amb llum ultravioleta i amb llum solar, va permetre obtindre 550 𝝁 mol*g-1 de H2 i 350 𝝁 mol*g-1 de H2 en 24 h respectivament, en les mateixes condicions de treball definides per a UiO66 (Zr/Ce/Ti). En este treball de tesi es va presentar per primera vegada la possibilitat de reduir 4-nitrofenol a través d'una metodologia tàndem que involucra primer la producció de H2 a partir d'aigua en presència de metanol, com a agent de sacrifici, i UiO66 (Zr) -NH2, com fotocatalizador, i la posterior reducció de 4-NP a 4-AP. D'altra banda, s'ha demostrat que els materials defectuosos amb estructura d'UiO66 poden reduir selectivament els dobles enllaços polaritzats X=Y en presència de gas H2., [EN] The present doctoral thesis has focused the attention on the synthesis of new MOFs materials obtained either by post-synthetic interchange of previously described MOFs or by heterojunction of stable MOFs having UiO66 structure. These materials have been applied as photocatalysts for the promising Overall Water Splitting reaction which claims to obtain H2 and O2 stoichiometrically starting from water in the absence of sacrificial agents or deposited metals nanoparticles. The new material UiO66 (Zr/Ce/Ti) showed surprising results in both UV- Visible light and sunlight irradiation conditions. Interesting results were also obtained in the case of the core-shell named UiO66(Zr)-NH225@UiO66(Ce) which, in the presence of water, when irradiated with both ultraviolet and solar light, allowed to obtain 550 𝝁 mol*g-1 of H2 and 350 𝝁 mol*g-1 of H2 in 24 h respectively, in the same working conditions defined for UiO66 (Zr/Ce/Ti). In this thesis was presented, for the first time, the possibility of reducing 4NP through a tandem methodology which, first, involves the production of H2 from water in the presence of methanol as a sacrificial agent and UiO66(Zr)-NH2 as a photo-catalyst, and subsequent the 4 NP reduction to 4 AP. On the other hand, it has been shown that defective materials with UiO66 structure can selectively reduce polarized X=Y double bonds in the presence of H2 gas.

This link provide information about: 1. Single cell data 2. High-current data 3. Geometry file for modelling 4. Figure 1C data 5. SEU data

[EN] 5-hydroxymethylfurfural (HMF) has been successfully valorized into 3-hydroxymethylcyclopentylamine through a one-pot cascade process in aqueous phase by coupling the hydrogenative ring-rearrangement of HMF into 3-hydroxymethylcyclopentanone (HCPN) with a subsequent reductive amination with ammonia. Mono- (Ni@C, Co@C) and bimetallic (NiCo@C) nanoparticles with different Ni/Co ratios partially covered by a thin carbon layer were prepared and characterized. Results showed that a NiCo catalyst, (molar ratio Ni/Co=1, Ni0.5Co0.5@C), displayed excellent performance in the hydrogenative ring-rearrangement of HMF into HCPN (>90 % yield). The high selectivity of the catalyst was attributed to the formation of NiCo alloy structures as hydrogenating sites that limited competitive reactions such as the hydrogenation of furan ring and the over-reduction of the formed HPCN. The subsequent reductive amination of HPCN with aqueous ammonia was performed giving the target cyclopentylaminoalcohol in 97 % yield. Moreover, the catalyst exhibited high stability maintaining its activity and selectivity for repeated reaction cycles., This work has been supported by the Spanish government through the "Severo Ochoa Program" (SEV-2016-0683) and the PGC2018-097277-B-100 (MCIU/AEI/FEDER, UE) project. The authors also thank Microscopy Service of UPV for the TEM measurements.

The introduction of thiophene rings to the helical structure of carbohelicenes has electronic effects that may be used advantageously in organic electronics. The performance of these devices is highly dependent on the sulfur atom topology, so a precise knowledge of the synthetic routes that may afford isomeric structures is necessary. We have studied the photocyclization pathway of both 2- and 3-styrylthiophenes on their way to thiahelicenes by experiment and theory. To begin with, the synthesis of stereochemically well-defined 2- and 3-styrylthiophenes allowed us to register first, and simulate later, the UV–vis electronic spectra of these precursors. This information gave us access through time-dependent density functional theory calculations to the very nature of the excited states involved in the photocyclization step and from there to the regio- and stereochemical outcome of the reaction. For the widely known case of a 2-styrylthiophene derivative, the expected naphtho[2,1-b]thiophene type of ring fusion was predicted and experimentally observed by synthesis. On the contrary, 3-styrylthiophene derivatives have been seldom used in synthetic photocyclizations. Among the two possible structural outcomes, only the naphtho[1,2-b]thiophene type of ring fusion was found to be mechanistically sound, and this was actually the only compound observed by synthesis. Financial support by the Spanish Ministerio de Economía y Competitividad (MAT2016-78625-C2-2-P), the Ministerio de Ciencia, Innovación y Universidades (PID2019-109539GB-C4 and PGC2018-096955-B-C44), the Generalitat Valenciana (PROMETEO/2017/139), and finally, the University of Alicante (VIGROB-285) is gratefully acknowledged. The computational resources provided by the Department of Applied Physics of the University of Alicante are greatly appreciated.

[EN] Using Pluronic P123 as a structure-directing agent and chitosan as a carbon precursor, different porous carbons with remarkable morphologies such as orthohedra or spheres with diametrically opposite holes are obtained. These particles of micrometric size are constituted by the stacking of thin sheets (60 nm) that become increasingly bent in the opposite sense, concave in the upper and convex in the bottom hemispheres, as the chitosan proportion increases. TEM images, after dispersion of the particles by sonication, show that besides micrometric graphene sheets, the material is constituted by nanometric onion-like carbons. The morphology and structure of these porous carbons can be explained based on the ability of Pluronic P123 to undergo self-assembly in aqueous solution due to its amphoteric nature and the filmogenic properties of chitosan to coat Pluronic P123 nanoobjects undergoing structuration and becoming transformed into nitrogen-doped graphitic carbons. XPS analysis reveals the presence of nitrogen in their composition. These porous carbons exhibit a significant CO2 adsorption capacity of above 3 mmol g(-1) under 100 kPa at 273 K attributable to their large specific surface area, ultraporosity, and the presence of basic N sites. In addition, the presence of dopant elements in the graphitic carbons opening the gap is responsible for the photocatalytic activity for H-2 generation in the presence of sacrificial electron donors, reaching a H-2 production of 63 mu mol g(-1) in 24 h., The Spanish Ministry of Science, Innovation and Universities (Severo Ochoa and RTI2018-89237-CO2-R1) and Generalitat Valenciana (Prometeo 2017/083).

[EN] Heteroarene boronate esters constitute valuable intermediates in modern organic synthesis. As building blocks, they can be further applied to the synthesis of new materials, since they can be easily transformed into any other functional group. Efforts toward novel and efficient strategies for their preparation are clearly desirable. Here, we have achieved the borylation of commercially available heteroarene halides under very mild conditions in an easy-to-use gel nanoreactor. Its use of visible light as the energy source at room temperature in photocatalyst-free and aerobic conditions makes this protocol very attractive. The gel network provides an adequate stabilizing microenvironment to support wide substrate scope, including furan, thiophene, selenophene, and pyrrole boronate esters., Financial support from the Generalitat Valenciana (CIDEGENT/2018/044) and the Spanish Ministry of Science and Innovation (PID2019-105391GB-C21, PID2019-105391GBC22, BEAGAL18/00166, and BES-2017-080215) is gratefully acknowledged. We thank the Electron Microscopy Service from the UPV and Prof. Julia Perez-Prieto for spectroscopy facilities. D.D.D. also thanks NANOtec, INTech, Cabildo de Tenerife, and ULL for laboratory facilities.

A presente pesquisa, de abordagem qualitativa participante, teve como objetivo analisar as percepções de estudantes do 3ª ano do Ensino Médio de um colégio estadual de Almirante Tamandaré/PR sobre a Metodologia Cooperativa, a qual fundamentou uma Sequência Didática envolvendo conteúdos de Química Orgânica. Os dados foram constituídos por meio de Grupo Focal e analisados a partir da Análise de Conteúdo. Das falas dos participantes da pesquisa emergiram quatro categorias que revelam suas percepções sobre: i) trabalho em grupo; ii) metodologia cooperativa desenvolvida; iii) aprendizagem dos conceitos químicos; e iv) método tradicional. As percepções apontaram que a metodologia ativa, pautada na Metodologia Cooperativa, se configurou como uma estratégia com potencialidade para promoção da aprendizagem de conceitos químicos, com destaque para o papel da interação social em sala de aula ao longo do processo educativo. Cooperative methodology in Chemistry teaching: perceptions of High School Students Abstract The present research, with a participative qualitative approach, aimed to analyze the perceptions of 3rd year high school students from a state school in Almirante Tamandaré / PR on Cooperative Methodology, which supported a Didactic Sequence involving Organic Chemistry content. The data were constituted through a Focus Group and analyzed based on Content Analysis. From the results, four categories emerged from the research participants' perceptions about: i) group work; ii) developed cooperative methodology; iii) learning of chemical concepts; and iv) traditional method. The perceptions pointed out that the active methodology, based on the Cooperative Methodology, was configured as an advantageous strategy, in the sense that it promoted the learning of chemical concepts and also caused the ability to overcome individual challenges, in addition to promoting confidence and creativity to work in groups. Keywords: Active Methodology. Teaching sequence. Organic chemistry.

[EN] beta-Galactosidase (beta-Gal) is a widely used enzyme as a reporter gene in the field of molecular biology which hydrolyzes the beta-galactosides into monosaccharides. beta-Gal is an essential enzyme in humans and its deficiency or its overexpression results in several rare diseases. Cellular senescence is probably one of the most relevant physiological disorders that involve beta-Gal enzyme. In this review, we assess the progress made to date in the design of molecular-based probes for the detection of beta-Gal both in vitro and in vivo. Most of the reported molecular probes for the detection of beta-Gal consist of a galactopyranoside residue attached to a signalling unit through glycosidic bonds. The beta-Gal-induced hydrolysis of the glycosidic bonds released the signalling unit with remarkable changes in color and/or emission. Additional examples based on other approaches are also described. The wide applicability of these probes for the rapid and in situ detection of de-regulation beta-Gal-related diseases has boosted the research in this fertile field, R.M laboratory members received the financial support from the Spanish Government (project RTI2018-100910-B-C41) and the Generalitat Valenciana (project PROMETEO 2018/024). B.L-T. received support from the Spanish Ministry of Economy for their PhD grants (FPU15/02707). J. F.-B received fellowship (CD19/00038)

[EN] For producing second-generation ethanol (cellulosic ethanol) and other value-added bioproducts, magnetic graphene oxide (GO-MNP) was synthesized in this work and used as the immobilization support for an industrial cellulase-and xylanase-containing preparation. GO-MNP characterization by TEM, SEM and ATR-FTIR spectroscopy showed that the magnetic nanoparticles are homogeneously distributed onto the GO sheets surface. The enzymatic preparation was immobilized by means of carbodiimide cross-linking chemistry using 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide and N-hydroxysuccinimide (NHS). The supported final biocatalyst (GO-MNP-Enz) showed high activity for the hydrolysis of pretreated sugarcane bagasse (PSB) and presented relative endoglucanase, xylanase, beta-glucosidase, and beta-xylosidase activities of 70%, 66%, 88%, and 70%, respectively, after 10 cycles of hydrolysis of their respective substrates. The biocatalyst also maintained approximately 50% and 80% of its efficiency for cellulose and xylan hydrolysis, respectively, being the TOF (g.g(-1).h(-1)) the highest observed when compared with previous results reported in literature. These findings suggest that GO-MNP-Enz may be a prospective candidate for industrial applications such as second-generation ethanol production. (C) 2020 Elsevier Ltd. All rights reserved., Sao Paulo State Research Support Foundation (FAPESP) contract number 2018/06241e3 funding this work. Coordination of Improvement of Higher Education Personnel (CAPES) funding the doctoral scholarship of Fernando Roberto Paz-Cedeno in Brazil and in the Universitat Politecnica de Valencia (UPV), Institute of Chemical Technology (ITQ), Valencia, Spain. Authors acknowledge financial support from PGC2018-097277-B-100 (MCIU/AEI/FEDER,UE) project and Severo Ochoa Program (SEV-2016-0683).

[EN] Celiac disease is a complex and autoimmune disorder caused by the ingestion of gluten affecting almost 1% of global population. Nowadays an effective treatment does not exist, and the only way to manage the disease is the removal of gluten from the diet. Owing the key role played by gluten, clear and regulated labelling of foodstuff and smart methods for gluten detection are needed to fight frauds on food industry and to avoid the involuntary ingestion of this protein by celiac patients. On that scope, the development of a novel detection system of gluten is here presented. The sensor consists of nanoporous anodic alumina films loaded with a fluorescent dye and capped with an aptamer that recognizes gliadin (gluten's soluble proteins). In the presence of gliadin, aptamer sequences displace from the surface of anodic alumina resulting in pore opening and dye delivery. The dispositive shows a limit of detection (LOD) of 100 mu g kg(-1) of gliadin, good selectivity and a detection time of approximately 60 min. Moreover, the sensor is validated in real food samples. This novel probe allows fast gluten detection through a simple signalling process with potential use for food control. (C) 2020 Elsevier B.V. All rights reserved., The authors want to thank the Spanish Government RTI2018-100910-B-C41 (MCUI/AEI/FEDER, UE) and the Generalitat Valenciana (project PROMETEO/2018/024) for support. L.P. thanks to Ministerio de Economia, Industria y Competitividad for his FPI grant. S.S.-F. thanks CIBER and ISCIII for her Sara Borrell contract. The authors also thank the Electron Microscopy Service at the UPV for support.

[EN] On-demand hydrogen release could be an important process for the transportation of fuel in the near future. Herein it is reported that the controlled thermolysis of HKUST-1 under optimal conditions generates structural defects resulting in a quasi-HKUST-1 material showing a 20-fold enhancement of the H-2 release turnover frequency at room temperature in the absence of a base, This work is based upon research funded by the Iran National Science Foundation (INSF) under project no. 4000089 and Spanish Ministry of Science and Innovation (Severo Ochoa and RTI201898237-CO2-1). Also, support for this investigation from Arak University is gratefully acknowledged.

Bimetallic PdCu nanoparticles can be applied as catalysts in a wide range of chemical and electrochemical reactions. This review article overviews the preparation and synthetic applications of these bimetallic nanoparticles (BNPs) developed mainly over the last 20 years. These BNPs show better catalytic activity and selectivity than the monometallic counterparts due to their electronic and structural interactions. Simple general preparation methods include reduction of the corresponding salt precursors by different agents, solvothermal processes and galvanic replacement. In the case of supported catalysts, mainly wet impregnation and in situ reduction processes are used. In addition, these nanomaterials are prepared with different Pd/Cu compositions and with different morphologies. In the case of supported materials, many solid supports especially alumina, silica, titania, ceria, magnetite, zeolites, active carbon, graphene, carbon nanotubes, resins and polymers are employed allowing the recovery and reuse of the supported catalyst. In addition, the presence of copper reduces the economic cost of using palladium in industrial processes. Among several synthetic applications, C–C bond forming reactions such as Suzuki–Miyaura, Sonogashira–Hagihara, Heck–Mizoroki, Guerbet and A3-coupling are efficiently performed with PdCu BNPs. Reduction reactions under PdCu catalysis such as nitrate reduction for water purification, hydrodechlorination of organic pollutants, hydrogenation of CO2 and CO to methanol, semihydrogenation of alkynes to alkenes, and hydrogenation of C[double bond, length as m-dash]C double bonds, furfural to furfuryl alcohol, polyols, levulinic and succinic acids to lactones, styrene oxide to 2-phenylethanol and nitroaromatics to aromatic amines can be successfully performed. In the case of electrocatalytic reductions, oxygen reduction to water, CO2 reductions to CO, to alcohols, to hydrocarbons and to formate and hydrogen generation from water splitting can be highlighted. In the field of oxidation reactions using oxygen, CO can be transformed into CO2, alcohols into aldehydes, cyclopentene to cyclopentanone, ethylene and acetic acid to vinyl acetate, and aromatic compounds can be hydroxylated to phenols. Electrooxidation reactions are useful processes especially for direct alcohol and formic acid fuel cells. The oxygen-assisted water gas shift reaction can be efficiently performed under PdCu catalysis. In the field of chemical sensors, PdCu BNPs can detect hydrogen in low concentrations, liquefied petroleum gas, formaldehyde, glucose, thiocyanate and phenols. Other applications such as catalysts in hydrosilylation of acetylenes to vinylsilanes and the use of PdCu NPs as antimicrobial agents are also described. The authors are grateful to the Institute for Advanced Studies in Basic Sciences (IASBS) Research Council and Iran National Science Foundation (INSF-Grant number of 97016837) for support of this work. We also thank the Spanish Ministerio de Economía, Industria y Competitividad, Agencia Estatal de Investigación (AEI) and Fondo Europeo de Desarrollo Regional (FEDER, EU) (projects CTQ2016-76782-P, CTQ2016-81797-REDC, and CTQ2017-85093-P), the Generalitat Valenciana (PROMETEOII/2014/017) and the University of Alicante for financial support.

The initial stages of the pandemic caused by SARS-CoV-2 showed that early detection of the virus in a simple way is the best tool until the development of vaccines. Many different tests are invasive or need the patient to cough up or even drag a sample of mucus from the throat area. Besides, the manufacturing time has proven insufficient in pandemic conditions since they were out of stock in many countries. Here we show a new method of manufacturing virus sensors and a proof of concept with SARS-CoV-2. We found that a fluorogenic peptide substrate of the main protease of the virus (Mpro) can be covalently immobilized in a polymer, with which a cellulose-based material can be coated. These sensory labels fluoresce with a single saliva sample of a positive COVID-19 patient. The results matched with that of the antigen tests in 22 of 26 studied cases (85% success rate)., We gratefully acknowledge the financial support provided by all funders. Author Saul Vallejos coordinates the project leading to these results, which has received funding from "La Caixa" Foundation, under agreement LCF/PR/PR18/51130007. This work was supported by the Regional Government of Castilla y León (Junta de Castilla y León) and by the Ministry of Science and Innovation MICIN and the European Union NextGenerationEU PRTR. Author Jose Miguel García received grant PID2020–113264RB-I00 funded by MCIN/AEI/ 10.13039/501100011033 and by “ERDF A way of making Europe”. Ana Arnaiz received funding from Ministerio de Universidades-European Union in the frame of NextGenerationEU RD 289/2021 (Universidad Politécnica de Madrid). Finally, all the authors want to thank the support provided by City Hall of Villadiego “Ayuntamiento de Villadiego” when looking for participants for the proof of concept.

We report on an innovative method to measure the Zn(II) concentration in commercial pet food samples, both wet and dry food. It is based on a colorimetric sensory polymer prepared from commercial monomers and 0.5 % of a synthetic monomer having a quinoline sensory core (N-(8-(2-azidoacetamido)quinolin-5-yl)methacrylamide). We obtained the sensory polymer as crosslinked films by thermally initiated bulk radical polymerization of the monomers of 100 μm thickness, which we punched into Ø6 mm sensory discs. The immersion of the discs in water solutions containing Zn(II) turned the fluorescence on, allowing for the titration of this cation using the G parameter of a digital picture taken to the discs. The limits of detection and quantification were 29 and 87 µg/L, respectively. Furthermore, we measured the concentration of Zn(II) even in the presence of other cations, detecting no significant interferences. Thus, in a further step, we obtained the concentration of Zn(II) from 15 commercial pet food samples, ranging from 19 to 198 mg/kg, following a simple extraction procedure and contacting the extractant with our sensory discs. These results were contrasted with that obtained by ICP-MS as a reference method., Spanish Agencia Estatal de Investigación (State Research Agency) (grant PID2020-113264RB-I00/AEI/10.13039/501100011033).

Background: Currently approved Alzheimer’s disease medications mainly comprise acetylcholinesterase inhibitors. Many of these inhibitors are either natural compounds or synthetic molecules inspired in natural compounds. Hybrid molecules that can interact with different target sites of the enzyme could lead to the discovery of effective multitarget drugs. Objective: To design, synthesize, and evaluate a series of new aza-resveratrol analogs as in vitro acetyl- and butyrylcholinesterase inhibitors. Methods: The synthesis is achieved by a simple and efficient microwave-assisted method, from commercially available starting materials. Compounds are designed as hybrids of an aza-stilbene nucleus (Schiff base) connected to a tertiary amine by a hydrocarbon chain of variable length, designed to interact both with the peripheric anionic site and the catalytic site of the enzyme. Results: All the derivatives inhibit both enzymes in a concentration-dependent manner, acting as moderate to potent cholinesterase inhibitors. The most potent inhibitors are compounds 12b (IC50 = 0.43 μM) and 12a (IC50 = 0.31 μM) for acetyl- and butyrylcholinesterase, respectively. Compounds 12a and 12b also exhibit significant acetylcholinesterase inhibition in SH-SY5Y human neuroblastoma cells without cytotoxic properties. Enzyme kinetic studies and molecular modeling reveal that inhibitor 12b targets both the catalytic active site and the peripheral anionic site of acetylcholinesterase what makes it able to modulate the self-induced β-amyloid aggregation. Furthermore, the molecular modeling analysis helps to assess the impact of the linker length in the inhibitory activity of this family of new cholinesterase inhibitors. Conclusion: These compounds have the potential to serve as a dual binding site inhibitor and might provide a useful template for the development of new anti-Alzheimer’s disease agents.

[EN] Supercapacitors (SCs), showing excellent power density, long service life, and high reversibility, have received great attention because of the increasing demand for energy storage devices. To further improve their performance, it is essential to develop advanced electrode materials. One group of materials, porous crystalline solids referred to as metal-organic frameworks (MOFs), have proved to be excellent templates for synthesizing functional materials to be employed in the preparation of electrodes for SCs. In comparison to monometallic MOFs, bimetallic MOFs and their derivatives offer a number of advantages, including tunable electrochemical activity, high charge capacity, and improved electrical conductivity. This review focuses on the use of MOF-derived bimetallic materials in SCs, the origin of the improved performance, and the latest developments in the field. Furthermore, the challenges and perspectives in this research area are discussed., This work was supported by Tarbiat Modares University and College of Engineering, Peking University. Financial support by the Spanish Ministry of Science and Innovation (Severo Ochoa and RTI2018-98237-CO2-1) and Generalitat Valenciana (Prometeo 2017-083) is gratefully acknowledged.

[EN] The adsorption of linear, monobranched and dibranched saturated hydrocarbons in the gasoline range has been studied on pure silica STW zeolite (Si-STW) by using pentane, hexane, and heptane isomers as model adsorbates. Experimental single-component adsorption isotherms and kinetic measurements together with configurational bias Monte Carlo (CBMC) and molecular dynamics (MD) simulations were carried out. Significant differences in both the equilibrium adsorption and especially the adsorption kinetics were found, which suggests that the separation of the quaternary-carbon dibranched isomer is feasible. The adsorption capacities and selectivities surpass those of pure silica MFI (Si-MFI), considered as reference. Altogether, Si-STW is presented as a promising adsorbent for increasing the octane number (ON) of the hydroisomerization product by selectively excluding quaternary-carbon dibranched hydrocarbons., We acknowledge the Spanish Ministry of Sciences, Innovation and Universities (MCIU), State Research Agency (AEI), and the European Fund for Regional Development (FEDER) for their funding via project RTI2018-101784-B-I00 and Program Severo Ochoa SEV-2016-0683. A.S. thanks the MCIU for his grant BES-2016-078684. E.P.B. thanks the MCIU for his grant (FPU15/01602). A.M. thanks the Generalitat Valenciana for a predoctoral fellowship GRISOLIAP/2019/084. A.M. and G.S. thank ASIC-UPV for the computational facilities. The Electron Microscopy Service of the UPV is acknowledged for their help in sample characterization.

[EN] Defect engineering in metal-organic frameworks is commonly performed by using thermal or chemical treatments. Herein we report that oxygen plasma treatment generates structural defects on MIL-125(Ti)-NH2, leading to an increase in its photocatalytic activity. Characterization data indicate that plasma-treated materials retain most of their initial crystallinity, while exhibiting somewhat lower surface area and pore volume. XPS and FT-IR spectroscopy reveal that oxygen plasma induces MIL-125(Ti)-NH2 partial terephthalate decarboxylation and an increase in the Ti-OH population. Thermogravimetric analyses confirm the generation of structural defects by oxygen plasma and allowed an estimation of the resulting experimental formula of the treated MIL-125(Ti)-NH2 solids. SEM analyses show that oxygen plasma treatment of MIL-125(Ti)-NH2 gradually decreases its particle size. Importantly, diffuse reflectance UV/Vis spectroscopy and valence band measurements demonstrate that oxygen plasma treatment alters the MIL-125(Ti)-NH2 band gap and, more significantly, the alignment of highest occupied and lowest unoccupied crystal orbitals. An optimal oxygen plasma treatment to achieve the highest efficiency in water splitting with or without methanol as sacrificial electron donor under UV/Vis or simulated sunlight was determined. The optimized plasma-treated MIL-125(Ti)-NH2 photocatalyst acts as a truly heterogeneous photocatalyst and retains most of its initial photoactivity and crystallinity upon reuse., S.N. thanks the Fundacion Ramon Areces (XVIII Concurso Nacional para la Adjudicacion de Ayudas a la Investigacion en Ciencias de la Vida y de la Materia, 2016), the Ministerio de Ciencia, Innovacion y Universidades RTI 2018-099482-A-I00 project, the Generalitat Valenciana grupos de investigacion consolidables 2019 (ref: AICO/2019/214) project, and the AVI project (INNEST/2020/111) for financial support. Financial support by the European Union (LoterCO2M), Spanish Ministry of Science, Innovation and Universities (Severo Ochoa and RTI2018-098237-B-C21), and Generalitat Valenciana (Prometeo 2017-083) is also gratefully acknowledged.

The first enantioselective alkylation of 5‐aminopyrazoles is described with good results. The organocatalytic alkylation of 5‐aminopyrazoles have been accomplished using benzoxathiazine 2,2‐dioxides as electrophiles and a bifunctional squaramide organocatalyst.

[EN] To achieve high-loading of stable subnanometric metal clusters on solid carriers is a challenge since those small metal clusters have strong tendency to sinter into larger nanoparticles. Development of facile synthesis methodologies to obtain subnanometric metal catalysts with high metal loading and high stability against sintering at high temperature (>500 degrees C) in reductive atmosphere (such as H-2) is critical for the practical applications. In this work, we will present and discuss the generation of high-loading (similar to 1.4 wt%) subnanometric Pt clusters confined in the sinusoidal channels of MFI zeolite, on the basis of the atomic-level understanding on the evolution of Pt and Sn species during high-temperature oxidation-reduction treatments. It will be shown that the structural evolution of Pt and Sn species is dependent on the post-synthesis treatments. The Pt particles on the external surface can disintegrate into subnanometric Pt species and get stabilized in the zeolite channels during high-temperature calcination in air while Sn species migrate from surface region to internal region during high-temperature reduction treatment at 650 degrees C. The resultant material containing bimetallic PtSn clusters confined in the 10MR sinusoidal channels of the purely siliceous MFI zeolite show excellent catalytic activity and stability, as demonstrated for dehydrogenation of light alkanes at high reaction temperature. (C) 2020 Elsevier Inc. All rights reserved., This work has been supported by the European Union through the European Research Council (grant ERC-AdG-2014-671093, SynCatMatch) and the Spanish government through the "Severo Ochoa Program"(SEV-2016-0683). The authors also thank Microscopy Service of UPV for the TEM and STEM measurements. The XAS measurements were carried out in CLAESS beamline of ALBA synchrotron and BM23 beamline at ESRF synchrotron. The kind supports from the scientific staffs in ALBA and ESRF are greatly appreciated. High-resolution STEM measurements were performed at DME-UCA node of ELECMI in Cadiz University, with financial support from FEDER/MINECO (MAT2017-87579-R and MAT2016-81118-P). C.W.L. thanks CAPES (Science without Frontiers Process no. 13191/13-6) for a predoctoral fellowship. Financial support on this work from ExxonMobil is greatly acknowledged.

[EN] Films of few-layers defective N-doped or undoped graphene (10-15 nm) containing antimony oxide nanoparticles (15-30 nm) have been prepared on quartz by pyrolysis of alginate or chitosan adsorbing Sb(OAc)(3). XPS shows that the prevalent Sb oxidation state is +III, while thermoprogrammed CO2 desorption shows that these films exhibit basic sites. These thin films have used as basic catalysts to promote the Michael addition of active methylene compounds and the Henry condensation. These results have been rationalized by DFT calculations that have shown that undercoordinated or two-fold coordinated oxygen atoms on SbOx clusters can act as basic sites, providing a wide range of basic strength. (c) 2020 Elsevier Inc. All rights reserved., This work was supported by UEFISCDI (PN-III-P4-ID-PCE-2016-0146, nr. 121/2017 and project number PN-III-P1-1.1-TE-2016-2191, nr. 89/2018) and by the Spanish Ministry of Science and Innovation (Severo Ochoa and RTI2018-890237-CO2-1).

CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico FAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais CAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior Reações de acoplamento Carbono-Carbono (C-C), catalisadas por paládio, estão entre as metodologias sintéticas mais importantes e usadas para a construção de estruturas moleculares orgânicas. A importância e relevância dessas metodologias foi reconhecida pela atribuição do prêmio Nobel de Química de 2010, aos pesquisadores, Heck, Negishi e Suzuki, que muito contribuíram nessa área. Estas reações normalmente são realizadas em solventes orgânicos anidros, alguns tóxicos, inflamáveis e caros. Na contramão dessas condições, tem surgido muitas alternativas, ambientalmente corretas, utilizando meios atóxicos e baratos como a água, dentro dos preceitos da Química Verde. O uso da água como solvente em reações catalisadas por paládio, para o acoplamento C-C, talvez seja umas das mais bem-vindas metodologias catalíticas em síntese orgânica, aliando eficiência, consciência ambiental e custo reduzido. Neste trabalho foram sintetizados catorze aldeídos iônicos, sendo dois com grupos de caráter aniônico (sulfonato e ácido carboxílico) e doze com grupos catiônicos, sendo seis com sítio imidazólio e seis com o sítio trifenilfosfônio, com rendimentos entre 65% e 99%. Obtido os aldeídos, estes foram submetidos a reação de condensação com a o-fenilenodiamina, obtendo-se catorze iminas com rendimentos entre 65 e 95%. Essas iminas foram utilizadas como ligantes para a obtenção de complexos iônicos de paládio(II), utilizando acetato de paládio(II) como fonte de paládio, com rendimentos que variaram entre 67% e 92%. Feita a síntese desses complexos, a próxima etapa foi a avaliação dos mesmos como catalisadores do acoplamento de Heck utilizando água como solvente. Inicialmente parâmetros como natureza da base, tipo de surfactante, temperatura e tempo de reação foram avaliados com o intuito de estabelecer a melhor condição reacional para a reação de Heck em água utilizando o bromobenzeno e estireno como substratos. Feito isso, os complexos sintetizados foram aplicados como catalisadores na reação de acoplamento e todos os complexos apresentaram uma atividade catalítica satisfatória com rendimentos variando de 54 a 100% na obtenção do produto de acoplamento. Quatro complexos de paládio(II) das bis-aminas iônicas, análogos reduzidos das bis-iminas iônicas foram obtidos com rendimentos entre 73 e 85%. Os testes de catálise do acoplamento de Heck com esses complexos como catalisadores forneceram rendimentos entre 48 e 85%, resultados próximos aos obtidos utilizando os análogos das bis-iminas. Carbon-Carbon coupling reactions catalyzed by palladium are among the most important and used synthetic methodologies for the construction of organic molecular structures. The importance and relevance of these methodologies was recognized by the award of the 2010 Nobel Prize in Chemistry to the researchers, Heck, Negishi and Suzuki, who contributed greatly in this area. These reactions are usually carried out in anhydrous organic solvents, some of which are toxic, flammable and expensive. Contrary to these conditions, many alternatives have emerged, environmentally correct, using non-toxic and cheap means such as water, within the precepts of Green Chemistry. The use of water as a solvent in palladium-catalyzed reactions for C-C coupling is perhaps one of the most welcome catalytic methodologies in organic synthesis, combining efficiency, environmental awareness and reduced cost. In this work, fourteen ionic aldehydes were synthesized, two of them with anionic groups (sulfonate and carboxylic acid) and twelve with cationic groups, six with imidazolium site and six with triphenylphosphonium site, with yields between 65 and 99%. Once the aldehydes were obtained, they were subjected to a condensation reaction with o-phenylenediamine, obtaining fourteen imines with yields between 65 and 95%. These imines, in turn, were used as binders to obtain ionic palladium(II) complexes, using palladium(II) acetate as palladium source, with yields ranging between 67 and 92%. The obtained palladium(II) complexes were used as catalysts in Heck coupling, using water as solvent. Initially parameters such as base, surfactant, temperature and time were evaluated in order to establish the best reaction condition for the Heck reaction in water using bromobenzene and styrene as substrate. After that, the synthesized complexes were applied as catalysts in the coupling reaction and all the complexes showed a satisfactory catalytic activity of 54 to 100% of yield in obtaining the coupling product. Four palladium(II) complexes of ionic bis-amines, reduced analogues of ionic bis-imines were obtained with yield between 73 and 85%. Heck coupling catalysis tests with these complexes as catalysts provided yields between 48 and 85%, results close to those obtained using the bis-imine analogues.