USC Repository :: Browsing by Author "Ellena, Javier"

Browsing by Author "Ellena, Javier"

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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, Javier
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
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, Javier
A 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.
Avoiding irreversible 5-fluorocytosine hydration: Via supramolecular synthesis of pharmaceutical cocrystals
(Royal Society of Chemistry, 2018-07-27) Souza, Matheus S.; Diniz, Luan F.; Vogt, Lautaro; Carvalho, Paulo S. Jr.; D’vries, Richard F.; Ellena, Javier
The antimetabolite 5-fluorocytosine (5-FC) was used to form pharmaceutical cocrystals in order to modulate its poor physicochemical stability in humid environments, which leads to the irreversible incorporation of a water molecule at the structural level under storage conditions. The anhydrous form of 5-FC is a well-known fluorinated analog of cytosine with antifungal activity and it has become one of the most used medications for cancer treatment via the gene therapy approach. In this study, novel 5-FC cocrystals were obtained from the reaction of 5-FC with three nontoxic coformers: caffeine (CAF), p-aminobenzoic acid (PABA) and caprylic acid (CA). These cocrystals, namely 5FC–CAF, 5FC–PABA and 5FC–CA, were characterized by single-crystal and powder X-ray diffraction (SCXRD and PXRD), spectroscopic (FT-IR and FT-Raman) and thermal (thermogravimetric analysis, differential scanning calorimetry, and hot-stage microscopy) techniques. The physical stabilities of 5-FC and its cocrystals were evaluated in environments with high relative humidity and the equilibrium solubility was measured in a pH 1.2 buffer medium. These studies show that the prodrug 5-FC is able to form different homo and heterosynthons that lead to cocrystal formation. Additionally, the solubility profiles of the novel multicomponent solid forms were found to be similar to the API raw material, a BCS class I drug, exhibiting a high solubility profile. The hydration stabilities of 5-FC and its cocrystals were evaluated in humid environments to confirm the irreversible hydration of 5-FC in contrast with the absence of phase transitions in its cocrystal forms. In this way all 5-FC cocrystals reported herein maintained to a large degree the API solubility and do not undergo the hydration process or phase transition under extreme storage conditions, being more stable than the parent 5-FC.
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, Javier
In 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.
Exploring physical and chemical properties in new multifunctional indium-, bismuth-, and zinc-based 1D and 2D coordination polymers
(Dalton Transactions, 2017) Gomez, German E.; D'vries, Richard Fernando; Lionello, Diego Fernando; Aguirre Díaz, Lina María; Costa, Cristina; Mariana, Spinosa; Fuertes, Maria Cecilia; Pizarro, Ramon A.; Kaczmarek, Anna M.; Ellena, Javier; Rozes, Laurence; Iglesias, Marta; Deun, Rik Van; Sanchez, Clement; Monge, Angeles; Soler Illia, Galo
Main group elements coordination polymers (MGE-CPs) are important compounds for the development of multifunctional materials. However, studies regarding to structural, optical, catalitic, mechanical or antibacterial properties have strikingly less reported. In this work, an exhaustive study of a set of crystalline MGE-CPs obtained from bismuth and indium metals, iminodiacetate, 1,2,4,5-benzenetetracarboxylate, and 2,2’-bipyridine as building blocks is presented. An in-deep topological analysis of the networks was carried out. Besides, nanoindentation studies were performed on two representative low dimensional compounds in order to find the relationships between their structural features and the intrinsic mechanical properties (hardness and elasticity). The solid state photoluminescence (SSPL) properties were also studied in terms of excitation, emission, lifetimes values and CIE chromaticites. Moreover, the heterogeneous catalytic activities of the compounds were evaluated in the cyanosilylation reaction using a set of carbonylic substrates under solvent-free conditions. Finally, the inhibitory effect of the Bi-CPs on the growth of microorganisms such as Escherichia coli, Salmonella enterica serovar Typhimurium and Pseudomonas aeruginosa, which are associated with relevant infectious diseases, is reported.
Luminescence, chemical sensing and mechanical properties of crystalline materials based on lanthanide-sulfonate coordination polymers
(RSC Advances, 2016) D’Vries, Richard F.; Gomez, German E.; Lionello, Diego F.; Fuertes, M. Cecilia; Soler Illia, Galo; Ellena, Javier
Lanthanide-coordination polymers (Ln-CPs) constitute relevant compounds for the design of multifunctional materials. Nevertheless, studies devoted to understand relationships of combined structural-optical-mechanical properties are scarcely reported. In this work, an exhaustive study of a series of CPs obtained from lanthanide metals, 3-hydroxinaphthalene-2,7-disulfonate(3-OHNDS) and 1,10-phenanthroline (phen) as ligands is presented. Two crystalline phases were identified with general formula [Eu(3-OHNDS)(Phen)(H2O)2]•3H2O (Phase 1-Eu), and [Ln2(3-OHNDS)2(Phen)2(H2O)]•3H2O (Phase 2-Ln), where Ln3+ = Tb, Dy, Ho, Er and Yb. Both phases were characterized by powder and single crystal X-ray diffraction, vibrational and thermal analysis and scanning electron microscopy. Moreover, nanoindentation analysis was performed in order to find relationships between structural features and the mechanical properties of the crystalline materials. The photoluminescence (PL) properties of the reported phases were also explored, involving excitation-emission experiments and quantification of color emission. Finally, one compound was selected as chemical sensor model, exhibiting different optical behaviour in the prescence of aromatic molecules, principally towards naphtalene molecules. These results make these compounds promising materials for the elaboration of selective chemical sensors.
Mechanochemical Synthesis of a Multicomponent Solid Form: The Case of 5-Fluorocytosine Isoniazid Codrug
(American Chemical Society, 2018-07-12) Souza, Matheus S.; Diniz, Luan F.; Vogt, Lautaro; Carvalho Jr., Paulo S.; D’vries, Richard F.; Ellena, Javier
Mechanochemistry synthesis was applied to the supramolecular synthesis and green scale-up production of a 1:1 drug–drug cocrystal involving the antimetabolite prodrug 5-Fluorocytosine (5-FC) and the tuberculostatic drug Isoniazid (INH), namely, 5FC-INH. Crystalline material, also obtained by traditional slow evaporation methods, was analyzed by single-crystal X-ray diffraction (XRD). The crystal packing is stabilized by a classical N–H···N hydrogen-bond interaction between the amine moiety of 5-FC and the INH pyridine nitrogen. IR and Raman data provided spectroscopic evidence about the hydrogen atom positions, thereby confirming the neutral nature of the cocrystal. Furthermore, 5FC-INH codrug was also evaluated by a range of analytical techniques such as powder XRD and thermal (thermogravimetric analysis, differential scanning calorimetry, hot stage microscopy) analyses. A physical stability study was performed in high relative humidity conditions to verify possible 5-FC solid-state hydration and/or INH degradation. The equilibrium solubility of this codrug was compared to the anhydrous 5-FC and INH raw materials, in pH 1.2 buffer media, and it was found to be similar to that of 5-FC, a biopharmaceutics classification system class I drug. The results show that the cocrystal has superior phase stability properties against moisture when compared to the starting pharmaceutical ingredients, so it could be considered as a potential candidate for the treatment of concomitant fungal infections, tuberculosis, and cancer.
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, Javier
Four 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.
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, Javier
Four 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.
Order-disorder phase transition induced by proton transfer in a co-crystal of 2,4-dichlorobenzoic acid and trimethylamine: N -oxide
(Royal Society of Chemistry, 2017-06-05) D'vries, Richard F.; Moreno Fuquen, Rodolfo; Camps, Ihosvany; Ayala, Alejandro Pedro; Kennedy, Alan R.; Reinheimer, Eric W.; Ellena, Javier
A crystalline binary adduct between trimethylamine N-oxide (TMANO) and 2,4-dichlorobenzoic acid (2,4-DCBA) molecules was obtained by slow evaporation from acetonitrile. The obtained molecular complex is formed by a racemic mixture of molecular complexes crystallizing in the orthorhombic space group Pbca. An exhaustive analysis of the temperature dependence of the cell parameters and the behavior of the acidic hydrogen position and carboxylate group was performed by single crystal and powder X-ray diffraction, FT-IR spectroscopy and theoretical calculations. The molecular system was thermally characterized, subsequently demonstrating an order–disorder transition. Finally, the intermolecular interactions were analyzed via Hirshfeld surface analysis.
Spergulagenic Acid A: Isolation and single crystal structure elucidation
(Elsevier B.V., 2019-07-19) Montoya, Guillermo; Gutierrez, Gustavo; D'Vries, Richard; Ellena, Javier; Panay, Aram J.
In the present work, the crystal structure of (3b)-3-acetoxy-30-methoxy-30-oxo-olean-12-en-28-oic acid, (Spergulagenic Acid A) is presented. The compound was isolated from Cecropia telenitida roots, employing semi-pilot scale extraction system and automated flash chromatography device. Vapor diffusion of methanol in chloroform yield suitable crystals for X-ray diffraction. The crystal packing of the Spergulagenic Acid A as methanol solvate is formed by strong hydrogen bonds between the SA-A molecule and the methanol. SA-A as well other pentacyclic triterpenes, present interesting potential biological activities. Inasmuch as biological activity is clearly related to molecular structure, the main goal of the present work was the structural elucidation of this molecule by single crystal X-ray diffraction. To the best of our knowledge, there is no previous crystal structure report in the literature for the titled compound or any other with simultaneous substitution at C2 and C7.
When serendipity knocks on the door: Synthesis and Physicochemical Characterization of 7-Chloro-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-5-one
(Sociedade Brasileira de Quimica, 2019-03-19) Carmona-Vargas, Christian C.; Ellena, Javier; D’Vries, Richard F.; Chaur, Manuel N.
Herein, we present the serendipitous obtaining of 7-chloro-2,3-dihydro-5H-thiazolo [3,2-a]pyrimidin-5-one in 40% yield by using POCl3 and a thiobarbituric acid derivative. The thiazolopyrimidine derivative was characterized by 1H nuclear magnetic resonance (NMR), UV-Vis, and Fourier transform infrared (FTIR) spectroscopy. Additionally, the structure was confirmed by single crystal X-ray diffraction, where it was found that the compound crystallizes in the P-1 triclinic space group with two conformeric molecules of 7-chloro-2,3-dihydro-5H-thiazolo [3,2-a]pyrimidin-5-one by asymmetric unit. Also, from the structural data was studied the supramolecular interactions using Hirshfeld surface analysis and 2D fingerprint plots. © 2019 Sociedade Brasileira de Química
When Serendipity Knocks on the Door: Synthesis and Physicochemical Characterization of 7-Chloro-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-5-one
(Journal of the Brazilian Chemical Society, 2019) Carmona-Vargas, Christian C.; Ellena, Javier; D’Vries, Richard F.; Chaur, Manuel N.
Herein, we present the serendipitous obtaining of 7-chloro-2,3-dihydro-5H-thiazolo [3,2-a]pyrimidin-5-one in 40% yield by using POCl3 and a thiobarbituric acid derivative. The thiazolopyrimidine derivative was characterized by 1H nuclear magnetic resonance (NMR), UV-Vis, and Fourier transform infrared (FTIR) spectroscopy. Additionally, the structure was conﬁrmed by single crystal X-ray diffraction, where it was found that the compound crystallizes in the P-1 triclinic space group with two conformeric molecules of 7-chloro-2,3-dihydro-5H-thiazolo [3,2-a]pyrimidin-5-one by asymmetric unit. Also, from the structural data was studied the supramolecular interactions using Hirshfeld surface analysis and 2D ﬁngerprint plots.

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