Browsing by Author "D'Vries, Richard F."
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Item 1D lanthanide coordination polymers based on lanthanides and 4′-hydroxi-4-biphenylcarboxylic acid: Synthesis, structures and luminescence properties(Journal of Solid State Chemistry, 2019) D'Vries, Richard F.; Gomez, German E.; Mondragon, Lina Paola; Onna, Diego; Barja, Beatriz C.; Soler Illia, Galo; Ellena, JavierA new family of 1D coordination polymers with formula [Ln(4-OHBBA) 3 (H 2 O) 2 ] and a new 3D supramolecular network topology was obtained. Photoluminescence and sensing tests of doped compounds were performed. Synopsis A family of coordination polymers with formula [Ln(4-OHBBA) 3 (H 2 O) 2 ] with a new 3D supramolecular network topology was obtained. Luminescence properties were studied. Resume A new family of 1D coordination polymers (CPs) based on 4'-hydroxi-4-biphenylcarboxylic acid (4-OHBBA) linker and lanthanide metals were obtained by hydrothermal synthesis. The compounds were fully characterized and present the general formula [Ln(4-OHBBA) 3 (H 2 O) 2 ] (where Ln= La, Pr), crystallizing in the monoclinic P2 1 /c space group. The CPs are formed by "fish bone-like" chains along [010] direction. Also, the topological analysis revels a 3D supramolecular structure with a 7-nodal 3,3,3,4,4,4,4-connected network and the (6.8 2) 2 (6 2 .8) 2 (6 3 .8 2 .10) 2 (6 3) 4 (6 5 .8) 2 (8 6) point symbol. The luminescence and chemical sensing tests of the europium doped compound was performed, finding that the Eu, Tb and Dy-doped samples exhibited dual emissions from the 4-OHBBA ligand and the lanthanide centres.Item 1D lanthanide coordination polymers based on lanthanides and 4′-hydroxi-4-biphenylcarboxylic acid: Synthesis, structures and luminescence properties(Academic Press Inc., 2019-03-29) D'Vries, Richard F.; Gomez, German E.; Mondragon, Lina Paola; Onna, Diego; Barja, Beatriz C.; Soler-Illia, Galo J.A.A.; Ellena, JavierSynopsis: A family of coordination polymers with formula [Ln(4-OHBBA) 3 (H 2 O) 2 ] with a new 3D supramolecular network topology was obtained. Luminescence properties were studied. Resume: A new family of 1D coordination polymers (CPs) based on 4′-hydroxi-4-biphenylcarboxylic acid (4-OHBBA) linker and lanthanide metals were obtained by hydrothermal synthesis. The compounds were fully characterized and present the general formula [Ln(4-OHBBA) 3 (H 2 O) 2 ] (where Ln = La, Pr), crystallizing in the monoclinic P2 1 /c space group. The CPs are formed by “fish bone-like” chains along [010] direction. Also, the topological analysis revels a 3D supramolecular structure with a 7-nodal 3,3,3,4,4,4,4-connected network and the (6.8 2 ) 2 (6 2 .8) 2 (6 3 .8 2 .10) 2 (6 3 ) 4 (6 5 .8) 2 (8 6 ) point symbol. The luminescence and chemical sensing tests of the europium doped compound was performed, finding that the Eu, Tb and Dy -doped samples exhibited dual emissions from the 4-OHBBA ligand and the lanthanide centresItem A facile synthesis of stable β-amino-N-/O-hemiacetals through a catalyst-free three-component Mannich-type reaction(Elsevier Ltd, 2017-03-02) Abonia, Rodrigo; Castillo, Juan C.; Garay, Alexander; Insuasty, Braulio; Quiroga, Jairo; Nogueras, Manuel; Cobo, Justo; D'Vries, Richard F.A practical, straightforward and one-step procedure for the synthesis of novel and stable b-amino-N-/Ohemiacetals (i.e. c-aminoalcohols) is provided. The title compounds were obtained in good to excellent yields through an uncatalyzed three-component reaction by treatment of secondary amines with polyformaldehyde and electron-rich alkenes in acetonitrile as solvent at ambient temperature. The reactions proceeded with the formation of iminium ions, through a Mannich-type reaction, as the key intermediates for the generation of the target products. Single crystal X-ray analysis of derivative 4l confirmed unequivocally the structure and stability of the obtained compounds.Item Data of synthesis, characterization and luminescence measurements in 1D lanthanide coordination polymers based on lanthanides(Elsevier Inc., 2019-10-22) D'Vries, Richard F.; Gomez, German E.; Mondragon, Lina Paola; Onna, Diego; Barja, Beatriz C.; Soler-Illia, Galo J.A.A.; Ellena, JavierIn this work are presented all the conditions of synthesis explored to obtain a new family of compound with formula [Ln(4-OHBBA)3(H2O)2] (Ln = La, Pr). Powder X ray diffraction was used to identify the different phases obtained in the synthetic study. FT-IR spectroscopy and TG analysis for La and Pr pure phases are also reported. Optical properties of optically active CPs materials, solid state photoluminescence properties of La, Pr, La-(5%Eu) and La-(5%Tb) compounds were explored. We report the absorption, excitation and emission spectrum of the 4′-hydroxi-4-biphenylcarboxylic acid and a comparative description of the radiative (and no-radiative) processes in solid state in Ln-(4-OHBBA) and Ln-BPDC compounds. Finally, a principal component analysis was conducted in order to take in account both signal contributions from the sensor (LCE at 384 nm and the europium emission at 610 nm) and for classifying the type of analytes used to test the sensing response of the materials.Item Determination of the binding constants of propeller-like metal complexes of picolinaldehyde-2-pyridylhydrazone(Elsevier S.A., 2018-12-13) Carmona Vargas, Christian C.; Aristizábal, Sandra L.; Belalcázar, María I.; D'Vries, Richard F.; Chaur, Manuel N.Herein, we determined the binding constants for transition metal complexes of Cu2+, Co2+, Fe2+, Ni2+, and Zn2+ ions formed with the ligand picolinaldehyde-2-pyridylhydrazone (PapyH) using the Benesi-Hildebrand method. Stoichiometry 2:1 (ligand: metal) was previously determined by the Job’s method and confirmed by single-crystal X-ray diffraction finding a propeller-like structure of the [Fe(Papy)2] compound. PapyH and the metal complexes were characterized by 1H NMR and UV-Vis spectroscopy, respectively. The Cu2+ complex exhibited the highest stability constant, which was confirmed by competitive reaction of different metal ions with the ligand PapyH.Item (E)-5-[1-Hydroxy-3-(3,4,5-trimethoxyphenyl)allylidene]-1,3-dimethylpyrimidine-2,4,6-trione: Crystal structure and Hirshfeld surface analysis(International Union of Crystallography, 2017-07-13) Soto-Monsalve, Mónica; Romero, Elkin L.; Zuluaga, Fabio; Chaur, Manuel N.; D'Vries, Richard F.In the title compound, C18H20N2O7, the dihedral angle between the aromatic rings is 7.28 (7)° and the almost planar conformation of the molecule is supported by an intramolecular O - H⋯O hydrogen bond, which closes an S(6) ring. In the crystal, weak C - H⋯O hydrogen bonds and aromatic π-π stacking link the molecules into a three-dimensional network. A Hirshfeld surface analysis showed that the major contribution to the intermolecular interactions are van der Waals interactions (H⋯H contacts), accounting for 48.4% of the surface. © Soto-Monsalve et al. 2017.Item Novel Isoniazid cocrystals with aromatic carboxylic acids: Crystal engineering, spectroscopy and thermochemical investigations(Elsevier B.V., 2017-09-30) Diniz, Luan F.; Souza, Matheus S.; Carvalho Jr, Paulo S.; da Silva, Cecilia C.P.; D'Vries, Richard F.; Ellena, JavierFour novel cocrystals of the anti-tuberculosis drug Isoniazid (INH), including two polymorphs, with the aromatic carboxylic acids p-nitrobenzoic (PNBA), p-cyanobenzoic (PCNBA) and p-aminobenzoic (PABA) were rationally designed and synthesized by solvent evaporation. Aiming to explore the possible supramolecular synthons of this API, these cocrystals were fully characterized by X-ray diffraction (SCXRD, PXRD), spectroscopic (FT-IR) and thermal (TGA, DSC, HSM) techniques. The cocrystal formation was found to be mainly driven by the synthons formed by the pyridine and hydrazide moieties. In both INH−PABA polymorphs, the COOH acid groups are H-bonded to pyridine and hydrazide groups giving rise to the acid⋯pyridine and acid⋯hydrazide heterosynthons. In INH−PNBA and INH−PCNBA cocrystals these acid groups are only related to the pyridine moiety. In addition to the structural study, supramolecular and Hirshfeld surface analysis were also performed based on the structural data. The cocrystals were identified from the FT-IR spectra and their thermal behaviors were studied by a combination of DSC, TGA and HSM techniques.Item Novel Isoniazid cocrystals with aromatic carboxylic acids: Crystal engineering, spectroscopy and thermochemical investigations(Journal of Molecular Structure, 2017) Diniz, Luan F.; Souza, Matheus S.; Carvalho Jr., Paulo S.; P. da Silva, Cecilia C.; D'Vries, Richard F.; Ellena, JavierFour novel cocrystals of the anti-tuberculosis drug Isoniazid (INH), including two polymorphs, with the aromatic carboxylic acids p-nitrobenzoic (PNBA), p-cyanobenzoic (PCNBA) and p-aminobenzoic (PABA) were rationally designed and synthesized by solvent evaporation. Aiming to explore the possible supramolecular synthons of this API, these cocrystals were fully characterized by X-ray diffraction (SCXRD, PXRD), spectroscopic (FT-IR) and thermal (TGA, DSC, HSM) techniques. The cocrystal formation was found to be mainly driven by the synthons formed by the pyridine and hydrazide moieties. In both INH−PABA polymorphs, the COOH acid groups are H-bonded to pyridine and hydrazide groups giving rise to the acid⋯pyridine and acid⋯hydrazide heterosynthons. In INH−PNBA and INH−PCNBA cocrystals these acid groups are only related to the pyridine moiety. In addition to the structural study, supramolecular and Hirshfeld surface analysis were also performed based on the structural data. The cocrystals were identified from the FT-IR spectra and their thermal behaviors were studied by a combination of DSC, TGA and HSM techniques.Item Rapanone, a naturally occurring benzoquinone, inhibits mitochondrial respiration and induces HepG2 cell death(Elsevier Ltd, 2019-11-20) Pardo Andreu, Gilberto L.; Zuccolotto DosReis, Felipe; González Durruthy, Michael; Delgado Hernández, René; D'Vries, Richard F.; Vanden Berghe, Wim; C. Alberici, LucianeRapanone is a natural occurring benzoquinone with several biological effects including unclear cytotoxic mechanisms. Here we addressed if mitochondria are involved in the cytotoxicity of rapanone towards cancer cells by employing hepatic carcinoma (HepG2) cells and isolated rat liver mitochondria. In the HepG2, rapanone (20–40 μM) induced a concentration-dependent mitochondrial membrane potential dissipation, ATP depletion, hydrogen peroxide generation and, phosphatidyl serine externalization; the latter being indicative of apoptosis induction. Rapanone toxicity towards primary rats hepatocytes (IC50 = 35.58 ± 1.50 μM) was lower than that found for HepG2 cells (IC50 = 27.89 ± 0.75 μM). Loading of isolated mitochondria with rapanone (5–20 μM) caused a concentration-dependent inhibition of phosphorylating and uncoupled respirations supported by complex I (glutamate and malate) or the complex II (succinate) substrates, being the latter eliminated by complex IV substrate (TMPD/ascorbate). Rapanone also dissipated mitochondrial membrane potential, depleted ATP content, released Ca2+ from Ca2+-loaded mitochondria, increased ROS generation, cytochrome c release and membrane fluidity. Further analysis demonstrated that rapanone prevented the cytochrome c reduction in the presence of decylbenzilquinol, identifying complex III as the site of its inhibitory action. Computational docking results of rapanone to cytochrome bc1 (Cyt bc1) complex from the human sources found spontaneous thermodynamic processes for the quinone-Qo and Qi binding interactions, supporting the experimental in vitro assays. Collectively, these observations suggest that rapanone impairs mitochondrial respiration by inhibiting electron transport chain at Complex III and promotes mitochondrial dysfunction. This property is potentially involved in rapanone toxicity on cancer cells.Item Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4- chlorophenylhydrazone)methyl)quinolone(Universidad Nacional de Colombia, 2018-12-02) Romero, Elkin L.; Soto-Monsalve, Mónica; Gutiérrez, Gustavo; Zuluaga, Fabio; D'Vries, Richard F.; Chaur, Manuel N.A novel molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinoline (1-E) was synthesized. Interconversion of 1-E to its configurational isomer 1-Z was achieved using UV radiation (250 W Hg lamp). Such isomerization was monitored by1H-NMR. The results suggest that the hydrazone derivative can act as a chemical brake in solution. This molecular system was structurally (Single Crystal X-Ray diffraction and DFT calculations) and spectroscopically (NMR, UV, and IR) characterized. Electrochemical measurements showed that configurational changes induce differential redox behavior. In this regard, the reported quinoline system exhibits different dynamic absorption and electrochemical properties that are modulated by UV-light. Therefore, 1-E can be regarded as a potential photo-electrochemical switch. © 2018, Universidad Nacional de Colombia. All rights reserved.Item Synthesis, structural characterization and theoretical studies of a new Schiff base 4-(((3-(tert-Butyl)-(1-phenyl)pyrazol-5-yl) imino)methyl)phenol(Elsevier B.V., 2017-09) Cuenú, Fernando; Londono Salazar, Jennifer; Torres, John Eduard; Abonia, Rodrigo; D'Vries, Richard F.4-(((3-(tert-Butyl)-(1-phenyl)pyrazol-5-yl)imino)methyl)phenol (4-OHFPz) was synthesized and characterized by FT-IR, MS, NMR, and single-crystal X-ray diffraction. Optimization of molecular geometry, vibrational frequencies, and chemical shifts were calculated by using the methods of density functional theory (DFT) with B3LYP and B3PW91 as functionals and Hartree-Fock with 6-311G++(d,p) as basis set using the GAUSSIAN 09 program package. With the VEDA 4 software, the vibrational frequencies were assigned in terms of the potential energy distribution (PED). The equilibrium geometries calculated by all methods were compared with X-ray diffraction results, indicating that the theoretical results matches well with the experimental ones. The data obtained from the vibrational analysis and the calculated NMR are consistent with the experimental spectra.