Browsing by Subject "Hydrogen bonding"

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    Exploiting 1,4-naphthoquinone and 3-iodo-1,4- naphthoquinone motifs as anion binding sites by hydrogen or halogen-bonding interactions
    (Royal Society of Chemistry, 2019-08-21) Navarro García, Encarnación; Velasco, María D.; Zapata Fernández, Fabiola; Bauzá, Antonio; Frontera, Antonio; Ramírez de Arellano, Carmen; Caballero, Antonio; Química Orgánica
    We describe here the utilization of 1,4-naphthoquinone and 3-iodo-1,4-naphthoquinone motifs as new anion binding sites by hydrogen- or halogen-bonding interactions, respectively. These binding sites have been integrated in bidentate ester based receptors. Emission experiments reveal that both receptors selectively recognize sulfate anions, which induced a remarkable increase of a new emission band attributed to the formation of π-stacking interactions between two 1,4-naphthoquinone units. Absorption spectroscopy and mass spectrometry indicate the disruption of the ester group of the 1,4- naphthoquinone based receptor in the presence of HP2O7 3−, H2PO4−, F−, AcO− and C6H5CO2− and in the halogenated receptor with HP2O7 3−, F− and AcO− anions, while the presence of sulfate anions showed the clasical complexation behaviour. The 1H-NMR experiment showed a slow exchange process of the receptors with their sulfate complexes. The binding mode of the receptors with sulfate has been studied by DFT calculations along with the Molecular Electrostatic Potential (MEP) surface computational tool that reveals those parts of the receptors which are more suitable for interacting with anions.
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    FAIR data for compunds included in the article "Maximizing the [c2]daisy chain to lasso ratio through competitive self-templating clipping reactions"
    (Universidad de Murcia, 2021-11-30) Saura-Sanmartin, Adrian; Pastor Vivero, Aurelia; Martinez-Cuezva, Alberto; Berná Cánovas, José; Química Orgánica
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    Hydrogen-bonded azaphenacene: a strategy for the organization of π-conjugated materials
    (2018-03-02) Gómez, Paula; Georgakopoulos, Stamatis; Cerón, José Pedro; da Silva, Iván; Más-Montoya, Miriam; Pérez, José; Tárraga Tomás, Alberto; Curiel Casado, David; Química Orgánica
    A centrosymmetric fused polyheteroaromatic system, namely 7-azaindolo[2,3-h]α-carboline has been synthesized. The pentacyclic structure includes rationally located hydrogen bond donor and hydrogen bond acceptor sites to induce its self-assembly. The molecular units associate forming an extended monodimensional arrangement that further self-organizes through π-stacking. The optical, electrochemical, X-ray diffraction, computational and electronic characterization in organic field effect transistors proves the utility of hydrogen bond-directed self-assembly as strategy to enhance edge-to-edge interactions and orbital overlap that contribute to the charge transport properties in π-conjugated systems.