Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds

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Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (en)
Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (sr)
Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (sr_RS)
Authors

Publications

Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study

Trisović, Nemanja; Radovanović, Lidija; Janjic, Goran V.; Jelić, Stefan; Rogan, Jelena

(Amer Chemical Soc, Washington, 2019)

TY  - JOUR
AU  - Trisović, Nemanja
AU  - Radovanović, Lidija
AU  - Janjic, Goran V.
AU  - Jelić, Stefan
AU  - Rogan, Jelena
PY  - 2019
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1205
AB  - A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N-H center dot center dot center dot O hydrogen bonds, which further self-organize through pairs of C-H center dot center dot center dot O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.
PB  - Amer Chemical Soc, Washington
T2  - Crystal Growth & Design
T1  - Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study
EP  - 2174
IS  - 4
SP  - 2163
VL  - 19
DO  - 10.1021/acs.cgd.8b01776
ER  - 
@article{
author = "Trisović, Nemanja and Radovanović, Lidija and Janjic, Goran V. and Jelić, Stefan and Rogan, Jelena",
year = "2019",
abstract = "A series of five derivatives of the anticonvulsant drug phenytoin was synthesized, and their crystal structures were determined. The relationship between the molecular and crystal structure of the investigated compounds was rationalized in the context of contribution of intermolecular interactions and supramolecular structural motifs. The conformational preferences were analyzed by comparing the rotational freedom of the phenyl groups in the investigated compounds with 5,5-diphenylhydantoins from the Cambridge Structural Database. With the exception of compound 3 bearing the cyclopropyl group, the crystal packing of the investigated compounds contains centrosymmetric dimers linked by paired N-H center dot center dot center dot O hydrogen bonds, which further self-organize through pairs of C-H center dot center dot center dot O interactions and a parallel interaction of two phenyl rings at a large offset into chains running along the c-axis. The principal feature of the crystal structure of compound 3 is formation of the chains by N-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions. The coordination of phenytoin enables more rotational freedom for the phenyl groups. An emphasis was placed on docking of the investigated compounds into the voltage-gated ion channel in the open and closed state. The obtained results indicate that hydrogen bonding and hydrophobic interactions are dominant in stabilizing energetically favored orientations of the investigated compounds bound to the protein.",
publisher = "Amer Chemical Soc, Washington",
journal = "Crystal Growth & Design",
title = "Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study",
pages = "2174-2163",
number = "4",
volume = "19",
doi = "10.1021/acs.cgd.8b01776"
}
Trisović, N., Radovanović, L., Janjic, G. V., Jelić, S.,& Rogan, J.. (2019). Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study. in Crystal Growth & Design
Amer Chemical Soc, Washington., 19(4), 2163-2174.
https://doi.org/10.1021/acs.cgd.8b01776
Trisović N, Radovanović L, Janjic GV, Jelić S, Rogan J. Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study. in Crystal Growth & Design. 2019;19(4):2163-2174.
doi:10.1021/acs.cgd.8b01776 .
Trisović, Nemanja, Radovanović, Lidija, Janjic, Goran V., Jelić, Stefan, Rogan, Jelena, "Substituent Effects on the Patterns of Intermolecular Interactions of 3-Alkyl and 3-Cycloalkyl Derivatives of Phenytoin: A Crystallographic and Quantum-Chemical Study" in Crystal Growth & Design, 19, no. 4 (2019):2163-2174,
https://doi.org/10.1021/acs.cgd.8b01776 . .
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3

On the azo dyes derived from benzoic and cinnamic acids used as photosensitizers in dye-sensitized solar cells

Matović, Luka; Tasić, Nikola; Trisović, Nemanja; Ladarević, Jelena; Vitnik, Vesna; Vitnik, Zeljko; Grgur, Branimir; Mijin, Dušan

(Scientific Technical Research Council Turkey-Tubitak, Ankara, 2019)

TY  - JOUR
AU  - Matović, Luka
AU  - Tasić, Nikola
AU  - Trisović, Nemanja
AU  - Ladarević, Jelena
AU  - Vitnik, Vesna
AU  - Vitnik, Zeljko
AU  - Grgur, Branimir
AU  - Mijin, Dušan
PY  - 2019
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1250
AB  - In order to get a better insight into the relationship between molecular structure and photovoltaic performance, six monoazo dye molecules containing benzoic and cinnamic acid moieties were synthesized and their photovoltaic properties were studied. Three of them have not been previously used in solar cells. Spectroscopic measurements of the investigated compounds coupled with theoretical calculations were performed. Short-circuit current density, open-circuit voltage, and fill-factor were determined. It was found that a larger amount of short-circuit current density will be generated if the HOMO-LUMO energy gap is lower, determined by the stability of the molecule and the electronic effect of the donor moiety. Among both series of synthesized dye molecules, the highest obtained values of short-circuit current density were achieved with (2-hydroxynaphthalene-1-ylazo)benzoic acid and (2-hydroxynaphthalene-1-ylazo)cinnamic acid, and thus they were regarded as promising candidates for application in dye-sensitized solar cells.
PB  - Scientific Technical Research Council Turkey-Tubitak, Ankara
T2  - Turkish Journal of Chemistry
T1  - On the azo dyes derived from benzoic and cinnamic acids used as photosensitizers in dye-sensitized solar cells
EP  - 1203
IS  - 4
SP  - 1183
VL  - 43
DO  - 10.3906/kim-1903-76
ER  - 
@article{
author = "Matović, Luka and Tasić, Nikola and Trisović, Nemanja and Ladarević, Jelena and Vitnik, Vesna and Vitnik, Zeljko and Grgur, Branimir and Mijin, Dušan",
year = "2019",
abstract = "In order to get a better insight into the relationship between molecular structure and photovoltaic performance, six monoazo dye molecules containing benzoic and cinnamic acid moieties were synthesized and their photovoltaic properties were studied. Three of them have not been previously used in solar cells. Spectroscopic measurements of the investigated compounds coupled with theoretical calculations were performed. Short-circuit current density, open-circuit voltage, and fill-factor were determined. It was found that a larger amount of short-circuit current density will be generated if the HOMO-LUMO energy gap is lower, determined by the stability of the molecule and the electronic effect of the donor moiety. Among both series of synthesized dye molecules, the highest obtained values of short-circuit current density were achieved with (2-hydroxynaphthalene-1-ylazo)benzoic acid and (2-hydroxynaphthalene-1-ylazo)cinnamic acid, and thus they were regarded as promising candidates for application in dye-sensitized solar cells.",
publisher = "Scientific Technical Research Council Turkey-Tubitak, Ankara",
journal = "Turkish Journal of Chemistry",
title = "On the azo dyes derived from benzoic and cinnamic acids used as photosensitizers in dye-sensitized solar cells",
pages = "1203-1183",
number = "4",
volume = "43",
doi = "10.3906/kim-1903-76"
}
Matović, L., Tasić, N., Trisović, N., Ladarević, J., Vitnik, V., Vitnik, Z., Grgur, B.,& Mijin, D.. (2019). On the azo dyes derived from benzoic and cinnamic acids used as photosensitizers in dye-sensitized solar cells. in Turkish Journal of Chemistry
Scientific Technical Research Council Turkey-Tubitak, Ankara., 43(4), 1183-1203.
https://doi.org/10.3906/kim-1903-76
Matović L, Tasić N, Trisović N, Ladarević J, Vitnik V, Vitnik Z, Grgur B, Mijin D. On the azo dyes derived from benzoic and cinnamic acids used as photosensitizers in dye-sensitized solar cells. in Turkish Journal of Chemistry. 2019;43(4):1183-1203.
doi:10.3906/kim-1903-76 .
Matović, Luka, Tasić, Nikola, Trisović, Nemanja, Ladarević, Jelena, Vitnik, Vesna, Vitnik, Zeljko, Grgur, Branimir, Mijin, Dušan, "On the azo dyes derived from benzoic and cinnamic acids used as photosensitizers in dye-sensitized solar cells" in Turkish Journal of Chemistry, 43, no. 4 (2019):1183-1203,
https://doi.org/10.3906/kim-1903-76 . .
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13

Hydro- and solvothermally-prepared ZnO and its catalytic effect on the photodegradation of Reactive Orange 16 dye

Simović, Bojana; Golubović, Aleksandar; Veljković, Ivana; Poleti, Dejan; Zdravković, Jelena; Mijin, Dušan; Bjelajac, Anđelika

(Srpsko hemijsko društvo, Beograd, 2014)

TY  - JOUR
AU  - Simović, Bojana
AU  - Golubović, Aleksandar
AU  - Veljković, Ivana
AU  - Poleti, Dejan
AU  - Zdravković, Jelena
AU  - Mijin, Dušan
AU  - Bjelajac, Anđelika
PY  - 2014
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/807
AB  - In this work, zinc oxide powders were obtained by two different techniques: hydro- and solvothermal synthesis starting from Zn(NO3)(2) and Zn(CH3COO)(2), respectively. The influence of synthetic procedure on the structural, microstructural, thermal and photocatalytic properties of the prepared ZnO powders was investigated. Both ZnO samples were further annealed under moderate conditions (300 degrees C) to avoid grain growth and to remove traces of impurities. In all four cases, single-phase hexagonal ZnO was confirmed by X-ray powder diffraction. The morphologies of prepared ZnO powders were different and they varied from rounded nanograins to microrods. All prepared samples showed higher photocatalytic efficiency in the degradation of the textile azo dye Reactive Orange 16 (RO16) than commercial ZnO. In addition, the non-annealed samples had better photocatalytic properties than the commercial Degussa P25 TiO2 powder.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Hydro- and solvothermally-prepared ZnO and its catalytic effect on the photodegradation of Reactive Orange 16 dye
EP  - 1443
IS  - 11
SP  - 1433
VL  - 79
DO  - 10.2298/JSC140520077S
ER  - 
@article{
author = "Simović, Bojana and Golubović, Aleksandar and Veljković, Ivana and Poleti, Dejan and Zdravković, Jelena and Mijin, Dušan and Bjelajac, Anđelika",
year = "2014",
abstract = "In this work, zinc oxide powders were obtained by two different techniques: hydro- and solvothermal synthesis starting from Zn(NO3)(2) and Zn(CH3COO)(2), respectively. The influence of synthetic procedure on the structural, microstructural, thermal and photocatalytic properties of the prepared ZnO powders was investigated. Both ZnO samples were further annealed under moderate conditions (300 degrees C) to avoid grain growth and to remove traces of impurities. In all four cases, single-phase hexagonal ZnO was confirmed by X-ray powder diffraction. The morphologies of prepared ZnO powders were different and they varied from rounded nanograins to microrods. All prepared samples showed higher photocatalytic efficiency in the degradation of the textile azo dye Reactive Orange 16 (RO16) than commercial ZnO. In addition, the non-annealed samples had better photocatalytic properties than the commercial Degussa P25 TiO2 powder.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Hydro- and solvothermally-prepared ZnO and its catalytic effect on the photodegradation of Reactive Orange 16 dye",
pages = "1443-1433",
number = "11",
volume = "79",
doi = "10.2298/JSC140520077S"
}
Simović, B., Golubović, A., Veljković, I., Poleti, D., Zdravković, J., Mijin, D.,& Bjelajac, A.. (2014). Hydro- and solvothermally-prepared ZnO and its catalytic effect on the photodegradation of Reactive Orange 16 dye. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 79(11), 1433-1443.
https://doi.org/10.2298/JSC140520077S
Simović B, Golubović A, Veljković I, Poleti D, Zdravković J, Mijin D, Bjelajac A. Hydro- and solvothermally-prepared ZnO and its catalytic effect on the photodegradation of Reactive Orange 16 dye. in Journal of the Serbian Chemical Society. 2014;79(11):1433-1443.
doi:10.2298/JSC140520077S .
Simović, Bojana, Golubović, Aleksandar, Veljković, Ivana, Poleti, Dejan, Zdravković, Jelena, Mijin, Dušan, Bjelajac, Anđelika, "Hydro- and solvothermally-prepared ZnO and its catalytic effect on the photodegradation of Reactive Orange 16 dye" in Journal of the Serbian Chemical Society, 79, no. 11 (2014):1433-1443,
https://doi.org/10.2298/JSC140520077S . .
1
1

Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones

Mirković, Jelena M.; Bozic, Bojan D.; Mutavdžić, Dragosav; Uscumlic, Gordana S.; Mijin, Dušan

(Elsevier Science Bv, Amsterdam, 2014)

TY  - JOUR
AU  - Mirković, Jelena M.
AU  - Bozic, Bojan D.
AU  - Mutavdžić, Dragosav
AU  - Uscumlic, Gordana S.
AU  - Mijin, Dušan
PY  - 2014
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/764
AB  - Spectral properties, solvatochromism and azo-hydrazone tautomerism of ten 5-(substituted phenylazo)3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones in twenty-two solvents are investigated. For quantitative evaluation of the solvent effects on the UV-vis absorption maxima, the principles of the linear solvation energy relationships are used, i.e. models proposed by Kamlet-Taft and Catalan. Linear free energy relationships are applied to the UV-vis absorption spectra and correlation of absorption frequencies with Hammett substituent constants are performed. Furthermore, the influence of the electronic nature of the substituents on H-1 and C-13 NMR shifts is investigated by simple and extended Hammett equations, as well as by Swain-Lupton equation.
PB  - Elsevier Science Bv, Amsterdam
T2  - Chemical Physics Letters
T1  - Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones
EP  - 68
SP  - 62
VL  - 615
DO  - 10.1016/j.cplett.2014.09.063
ER  - 
@article{
author = "Mirković, Jelena M. and Bozic, Bojan D. and Mutavdžić, Dragosav and Uscumlic, Gordana S. and Mijin, Dušan",
year = "2014",
abstract = "Spectral properties, solvatochromism and azo-hydrazone tautomerism of ten 5-(substituted phenylazo)3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones in twenty-two solvents are investigated. For quantitative evaluation of the solvent effects on the UV-vis absorption maxima, the principles of the linear solvation energy relationships are used, i.e. models proposed by Kamlet-Taft and Catalan. Linear free energy relationships are applied to the UV-vis absorption spectra and correlation of absorption frequencies with Hammett substituent constants are performed. Furthermore, the influence of the electronic nature of the substituents on H-1 and C-13 NMR shifts is investigated by simple and extended Hammett equations, as well as by Swain-Lupton equation.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Chemical Physics Letters",
title = "Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones",
pages = "68-62",
volume = "615",
doi = "10.1016/j.cplett.2014.09.063"
}
Mirković, J. M., Bozic, B. D., Mutavdžić, D., Uscumlic, G. S.,& Mijin, D.. (2014). Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones. in Chemical Physics Letters
Elsevier Science Bv, Amsterdam., 615, 62-68.
https://doi.org/10.1016/j.cplett.2014.09.063
Mirković JM, Bozic BD, Mutavdžić D, Uscumlic GS, Mijin D. Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones. in Chemical Physics Letters. 2014;615:62-68.
doi:10.1016/j.cplett.2014.09.063 .
Mirković, Jelena M., Bozic, Bojan D., Mutavdžić, Dragosav, Uscumlic, Gordana S., Mijin, Dušan, "Solvent and structural effects on the spectral shifts of 5-(substituted phenylazo)-3-cyano-6-hydroxy-1-(2-hydroxyethyl)-4-methyl-2-pyridones" in Chemical Physics Letters, 615 (2014):62-68,
https://doi.org/10.1016/j.cplett.2014.09.063 . .
15
11
14

Voltammetric and Square-Wave Anodic Stripping Determination of Amlodipine Besylate on Gold Electrode

Stoiljković, Z.Z.; Avramov-Ivić, Milka L; Petrović, S.D.; Mijin, Dušan; Stevanović, Sanja I.; Lačnjevac, Uroš; Marinković, Aleksandar

(Electrochemical Science Group, Beograd, 2012)

TY  - JOUR
AU  - Stoiljković, Z.Z.
AU  - Avramov-Ivić, Milka L
AU  - Petrović, S.D.
AU  - Mijin, Dušan
AU  - Stevanović, Sanja I.
AU  - Lačnjevac, Uroš
AU  - Marinković, Aleksandar
PY  - 2012
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/610
AB  - The oxidative behaviour of amlodipine besylate was studied. The gold electrode and Au/o-MWCNT (oxidized multi-wall carbon nanotubes) were used for determination of amlodipine besylate standard and as a content of Alopres tablet, in 0.05 M NaHCO3 and in phosphate buffer (pH=11) by cyclic voltammetry and square-wave anodic stripping voltammetry. Electrode surfaces were characterized by AFM in the presence of amlodipine and the concentrations of drugs in electrolytes were simultaneously followed by HPLC. The linear dependency of the anodic currents of amlodipine besylate as standard and in Alopres tablet vs. concentration was observed in both electrolytes, but in phosphate buffer for the higher concentrations. The peak currents obtained in all experiments are more than fifty-fold higher comparing to all previously published results concerning the glassy carbon electrode and the carbon paste electrode. The gold electrode is better catalyst for anodic oxidation of amlodipine besylate than glassy carbone. The results obtained with Au/o-MWCNT show lower anodic activity comparing to previously published GC/o-MWCNT. GC/o-MWCNT is better catalyst than Au/o-MWCNT under similar experimental conditions.
PB  - Electrochemical Science Group, Beograd
T2  - International Journal of Electrochemical Science
T1  - Voltammetric and Square-Wave Anodic Stripping Determination of Amlodipine Besylate on Gold Electrode
EP  - 2303
IS  - 3
SP  - 2288
VL  - 7
UR  - https://hdl.handle.net/21.15107/rcub_cer_1019
ER  - 
@article{
author = "Stoiljković, Z.Z. and Avramov-Ivić, Milka L and Petrović, S.D. and Mijin, Dušan and Stevanović, Sanja I. and Lačnjevac, Uroš and Marinković, Aleksandar",
year = "2012",
abstract = "The oxidative behaviour of amlodipine besylate was studied. The gold electrode and Au/o-MWCNT (oxidized multi-wall carbon nanotubes) were used for determination of amlodipine besylate standard and as a content of Alopres tablet, in 0.05 M NaHCO3 and in phosphate buffer (pH=11) by cyclic voltammetry and square-wave anodic stripping voltammetry. Electrode surfaces were characterized by AFM in the presence of amlodipine and the concentrations of drugs in electrolytes were simultaneously followed by HPLC. The linear dependency of the anodic currents of amlodipine besylate as standard and in Alopres tablet vs. concentration was observed in both electrolytes, but in phosphate buffer for the higher concentrations. The peak currents obtained in all experiments are more than fifty-fold higher comparing to all previously published results concerning the glassy carbon electrode and the carbon paste electrode. The gold electrode is better catalyst for anodic oxidation of amlodipine besylate than glassy carbone. The results obtained with Au/o-MWCNT show lower anodic activity comparing to previously published GC/o-MWCNT. GC/o-MWCNT is better catalyst than Au/o-MWCNT under similar experimental conditions.",
publisher = "Electrochemical Science Group, Beograd",
journal = "International Journal of Electrochemical Science",
title = "Voltammetric and Square-Wave Anodic Stripping Determination of Amlodipine Besylate on Gold Electrode",
pages = "2303-2288",
number = "3",
volume = "7",
url = "https://hdl.handle.net/21.15107/rcub_cer_1019"
}
Stoiljković, Z.Z., Avramov-Ivić, M. L., Petrović, S.D., Mijin, D., Stevanović, S. I., Lačnjevac, U.,& Marinković, A.. (2012). Voltammetric and Square-Wave Anodic Stripping Determination of Amlodipine Besylate on Gold Electrode. in International Journal of Electrochemical Science
Electrochemical Science Group, Beograd., 7(3), 2288-2303.
https://hdl.handle.net/21.15107/rcub_cer_1019
Stoiljković Z, Avramov-Ivić ML, Petrović S, Mijin D, Stevanović SI, Lačnjevac U, Marinković A. Voltammetric and Square-Wave Anodic Stripping Determination of Amlodipine Besylate on Gold Electrode. in International Journal of Electrochemical Science. 2012;7(3):2288-2303.
https://hdl.handle.net/21.15107/rcub_cer_1019 .
Stoiljković, Z.Z., Avramov-Ivić, Milka L, Petrović, S.D., Mijin, Dušan, Stevanović, Sanja I., Lačnjevac, Uroš, Marinković, Aleksandar, "Voltammetric and Square-Wave Anodic Stripping Determination of Amlodipine Besylate on Gold Electrode" in International Journal of Electrochemical Science, 7, no. 3 (2012):2288-2303,
https://hdl.handle.net/21.15107/rcub_cer_1019 .
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