TY  - JOUR
AU  - Janjic, Goran V.
AU  - Jelić, Stefan
AU  - Trisović, Nemanja
AU  - Popović, Dragan M.
AU  - Đorđević, Ivana S.
AU  - Milcic, Milos. K.
PY  - 2020
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1357
AB  - Fluorination of compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of groups in their vicinity. The formation of F center dot center dot center dot F interactions is followed by the shift of the electron density in the area of F center dot center dot center dot F contact, which creates a new region with a larger surface area, a higher negative potential, and, hence, a more pronounced accepting ability. The new region also has a greater ability to form multiple (simultaneous) interactions with species from the environment, thus compensating for the reduction of the accepting capacity of the groups in the vicinity. This phenomenon explains not only the abundance of F center dot center dot center dot F interactions in crystal structures, but also a large number of structures with F center dot center dot center dot O interactions. Only C-H center dot center dot center dot F interactions are more numerous than F center dot center dot center dot F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups.
PB  - Amer Chemical Soc, Washington
T2  - Crystal Growth & Design
T1  - New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures
EP  - 2951
IS  - 5
SP  - 2943
VL  - 20
DO  - 10.1021/acs.cgd.9b01565
ER  - 

@article{
author = "Janjic, Goran V. and Jelić, Stefan and Trisović, Nemanja and Popović, Dragan M. and Đorđević, Ivana S. and Milcic, Milos. K.",
year = "2020",
abstract = "Fluorination of compounds causes an increase in the proton-donating ability and a decrease in the proton-accepting capacity of groups in their vicinity. The formation of F center dot center dot center dot F interactions is followed by the shift of the electron density in the area of F center dot center dot center dot F contact, which creates a new region with a larger surface area, a higher negative potential, and, hence, a more pronounced accepting ability. The new region also has a greater ability to form multiple (simultaneous) interactions with species from the environment, thus compensating for the reduction of the accepting capacity of the groups in the vicinity. This phenomenon explains not only the abundance of F center dot center dot center dot F interactions in crystal structures, but also a large number of structures with F center dot center dot center dot O interactions. Only C-H center dot center dot center dot F interactions are more numerous than F center dot center dot center dot F interactions in crystal structures, which indicates a high affinity of fluorinated compounds for nonpolar groups.",
publisher = "Amer Chemical Soc, Washington",
journal = "Crystal Growth & Design",
title = "New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures",
pages = "2951-2943",
number = "5",
volume = "20",
doi = "10.1021/acs.cgd.9b01565"
}

Janjic, G. V., Jelić, S., Trisović, N., Popović, D. M., Đorđević, I. S.,& Milcic, Milos. K.. (2020). New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures. in Crystal Growth & Design
Amer Chemical Soc, Washington., 20(5), 2943-2951.
https://doi.org/10.1021/acs.cgd.9b01565

Janjic GV, Jelić S, Trisović N, Popović DM, Đorđević IS, Milcic MK. New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures. in Crystal Growth & Design. 2020;20(5):2943-2951.
doi:10.1021/acs.cgd.9b01565 .

Janjic, Goran V., Jelić, Stefan, Trisović, Nemanja, Popović, Dragan M., Đorđević, Ivana S., Milcic, Milos. K., "New Theoretical Insight into Fluorination and Fluorine-Fluorine Interactions as a Driving Force in Crystal Structures" in Crystal Growth & Design, 20, no. 5 (2020):2943-2951,
https://doi.org/10.1021/acs.cgd.9b01565 . .

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 . .

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 . .

TY  - JOUR
AU  - Marković, Jelena M.
AU  - Trisović, Nemanja
AU  - Mutavdžić, Dragosav
AU  - Radotić, Ksenija
AU  - Juranic, Ivan O.
AU  - Drakulic, Branko J.
AU  - Marinković, Aleksandar
PY  - 2015
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/885
AB  - Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogen-bond acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified using the Kamlet-Taft and Catalan approach. The obtained results were rationalized by comparison of electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HE, DFT, MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silica obtained conformational assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used to estimate population of conformers and to deconvolute the UV-Vis spectrum of representative derivative; inferring that the conformational assembly is more complex than was assumed in so far published literature data for this class of compounds. Along with this, the emission spectra of the representative compounds were decomposed by the Multivariate Curve Resolution analysis.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study
EP  - 446
SP  - 435
VL  - 135
DO  - 10.1016/j.saa.2014.07.023
ER  - 

@article{
author = "Marković, Jelena M. and Trisović, Nemanja and Mutavdžić, Dragosav and Radotić, Ksenija and Juranic, Ivan O. and Drakulic, Branko J. and Marinković, Aleksandar",
year = "2015",
abstract = "Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogen-bond acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified using the Kamlet-Taft and Catalan approach. The obtained results were rationalized by comparison of electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HE, DFT, MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silica obtained conformational assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used to estimate population of conformers and to deconvolute the UV-Vis spectrum of representative derivative; inferring that the conformational assembly is more complex than was assumed in so far published literature data for this class of compounds. Along with this, the emission spectra of the representative compounds were decomposed by the Multivariate Curve Resolution analysis.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study",
pages = "446-435",
volume = "135",
doi = "10.1016/j.saa.2014.07.023"
}

Marković, J. M., Trisović, N., Mutavdžić, D., Radotić, K., Juranic, I. O., Drakulic, B. J.,& Marinković, A.. (2015). Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
Pergamon-Elsevier Science Ltd, Oxford., 135, 435-446.
https://doi.org/10.1016/j.saa.2014.07.023

Marković JM, Trisović N, Mutavdžić D, Radotić K, Juranic IO, Drakulic BJ, Marinković A. Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2015;135:435-446.
doi:10.1016/j.saa.2014.07.023 .

Marković, Jelena M., Trisović, Nemanja, Mutavdžić, Dragosav, Radotić, Ksenija, Juranic, Ivan O., Drakulic, Branko J., Marinković, Aleksandar, "Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 135 (2015):435-446,
https://doi.org/10.1016/j.saa.2014.07.023 . .