TY  - JOUR
AU  - Jakšić, Jovana
AU  - Milinković, Evgenija
AU  - Cvetanović, Katarina
AU  - Vujošević, Zorana Tokić
AU  - Jovanov, Vladislav
AU  - Mitrović, Aleksandra
AU  - Maslak, Veselin
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7231
AB  - In this study, we conducted a comprehensive investigation of newly synthesized fullerene derivatives developed for potential application in perovskite solar cells (PSCs). We explored three novel dihydrofuran-fused C60 fullerene derivatives (13, 14, and 15) that were specifically designed to enhance solubility and interaction with the substrate, fluorine-doped tin oxide (FTO). A comparative analysis was performed, with reference to the widely used phenyl-C61-butyric acid methyl ester (PCBM) and compound 12, from which 13, 14, and 15 are derived, to assess the impact of sugar units on materials properties. The synthesized compounds demonstrated significant solubility in common organic solvents, a critical factor in their potential application in wet-processed PSCs. Our investigation included electrochemical property analysis, thin film deposition, surface characterization, and electrochemical impedance spectroscopy (EIS). EIS measurements unveiled key insights into charge transfer properties at the electrode/electrolyte interface, making the compounds attractive candidates for electron transport layers (ETLs) in PSCs.
PB  - Royal Society of Chemistry (RSC)
T2  - Physical Chemistry Chemical Physics
T1  - Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study
VL  - 26
IS  - 1
SP  - 517
EP  - 523
DO  - 10.1039/D3CP04322C
ER  - 

@article{
author = "Jakšić, Jovana and Milinković, Evgenija and Cvetanović, Katarina and Vujošević, Zorana Tokić and Jovanov, Vladislav and Mitrović, Aleksandra and Maslak, Veselin",
year = "2023",
abstract = "In this study, we conducted a comprehensive investigation of newly synthesized fullerene derivatives developed for potential application in perovskite solar cells (PSCs). We explored three novel dihydrofuran-fused C60 fullerene derivatives (13, 14, and 15) that were specifically designed to enhance solubility and interaction with the substrate, fluorine-doped tin oxide (FTO). A comparative analysis was performed, with reference to the widely used phenyl-C61-butyric acid methyl ester (PCBM) and compound 12, from which 13, 14, and 15 are derived, to assess the impact of sugar units on materials properties. The synthesized compounds demonstrated significant solubility in common organic solvents, a critical factor in their potential application in wet-processed PSCs. Our investigation included electrochemical property analysis, thin film deposition, surface characterization, and electrochemical impedance spectroscopy (EIS). EIS measurements unveiled key insights into charge transfer properties at the electrode/electrolyte interface, making the compounds attractive candidates for electron transport layers (ETLs) in PSCs.",
publisher = "Royal Society of Chemistry (RSC)",
journal = "Physical Chemistry Chemical Physics",
title = "Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study",
volume = "26",
number = "1",
pages = "517-523",
doi = "10.1039/D3CP04322C"
}

Jakšić, J., Milinković, E., Cvetanović, K., Vujošević, Z. T., Jovanov, V., Mitrović, A.,& Maslak, V.. (2023). Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study. in Physical Chemistry Chemical Physics
Royal Society of Chemistry (RSC)., 26(1), 517-523.
https://doi.org/10.1039/D3CP04322C

Jakšić J, Milinković E, Cvetanović K, Vujošević ZT, Jovanov V, Mitrović A, Maslak V. Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study. in Physical Chemistry Chemical Physics. 2023;26(1):517-523.
doi:10.1039/D3CP04322C .

Jakšić, Jovana, Milinković, Evgenija, Cvetanović, Katarina, Vujošević, Zorana Tokić, Jovanov, Vladislav, Mitrović, Aleksandra, Maslak, Veselin, "Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study" in Physical Chemistry Chemical Physics, 26, no. 1 (2023):517-523,
https://doi.org/10.1039/D3CP04322C . .

TY  - JOUR
AU  - Nešić, Maja D.
AU  - Dučić, Tanja
AU  - Liang, Xinyue
AU  - Algarra, Manuel
AU  - Mi, Lan
AU  - Korićanac, Lela
AU  - Žakula, Jelena
AU  - Kop, Tatjana
AU  - Bjelaković, Mira
AU  - Mitrović, Aleksandra
AU  - Gojgić-Cvijović, Gordana
AU  - Stepić, Milutin
AU  - Petković, Marijana
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3891
AB  - Abstract
Objects of the present study are improved fullerene C60 drug carrier properties trough encapsulation by microbial polysaccharides, levan (LEV), pullulan (PUL), and their hydrophobized cholesterol-derivatives (CHL and CHP), that show better interaction with cancer cells. The zeta potential, polydispersity index, and the diameter of particles were determined, and their cytotoxicity against three cancer cell lines were tested. Biochemical changes in HeLa cells are analyzed by synchrotron radiation (SR) FTIR spectro-microscopy combined with the principal component analysis (PCA). The most significant changes occur in HeLa cells treated with LEV-C60 and correspond to the changes in the protein region, i.e. Amide Iband, and the changes in the structure of lipid bodies and membrane fluidity are evident. The highest cytotoxicity was also induced by LEV-C60. In HeLa cells, cytotoxicity could not be strictly associated with biochemical changes in lipids, proteins and nucleic acids, but these findings are significant contribution to the study of the mechanism of interaction of C60-based nanoparticles with cellular biomolecules. In conclusion, LEV, PUL, CHL, and CHP enhanced fullerene C60potential to be used as target drug delivery system with the ability to induce specific intracellular changes in HeLa cancer cells.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - SR-FTIR spectro-microscopic interaction study of biochemical changes in HeLa cells induced by Levan-C60, Pullulan-C60, and their cholesterol-derivatives
VL  - 165
IS  - B
SP  - 2541
EP  - 2549
DO  - 10.1016/j.ijbiomac.2020.10.141
ER  - 

@article{
author = "Nešić, Maja D. and Dučić, Tanja and Liang, Xinyue and Algarra, Manuel and Mi, Lan and Korićanac, Lela and Žakula, Jelena and Kop, Tatjana and Bjelaković, Mira and Mitrović, Aleksandra and Gojgić-Cvijović, Gordana and Stepić, Milutin and Petković, Marijana",
year = "2020",
abstract = "Abstract
Objects of the present study are improved fullerene C60 drug carrier properties trough encapsulation by microbial polysaccharides, levan (LEV), pullulan (PUL), and their hydrophobized cholesterol-derivatives (CHL and CHP), that show better interaction with cancer cells. The zeta potential, polydispersity index, and the diameter of particles were determined, and their cytotoxicity against three cancer cell lines were tested. Biochemical changes in HeLa cells are analyzed by synchrotron radiation (SR) FTIR spectro-microscopy combined with the principal component analysis (PCA). The most significant changes occur in HeLa cells treated with LEV-C60 and correspond to the changes in the protein region, i.e. Amide Iband, and the changes in the structure of lipid bodies and membrane fluidity are evident. The highest cytotoxicity was also induced by LEV-C60. In HeLa cells, cytotoxicity could not be strictly associated with biochemical changes in lipids, proteins and nucleic acids, but these findings are significant contribution to the study of the mechanism of interaction of C60-based nanoparticles with cellular biomolecules. In conclusion, LEV, PUL, CHL, and CHP enhanced fullerene C60potential to be used as target drug delivery system with the ability to induce specific intracellular changes in HeLa cancer cells.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "SR-FTIR spectro-microscopic interaction study of biochemical changes in HeLa cells induced by Levan-C60, Pullulan-C60, and their cholesterol-derivatives",
volume = "165",
number = "B",
pages = "2541-2549",
doi = "10.1016/j.ijbiomac.2020.10.141"
}

Nešić, M. D., Dučić, T., Liang, X., Algarra, M., Mi, L., Korićanac, L., Žakula, J., Kop, T., Bjelaković, M., Mitrović, A., Gojgić-Cvijović, G., Stepić, M.,& Petković, M.. (2020). SR-FTIR spectro-microscopic interaction study of biochemical changes in HeLa cells induced by Levan-C60, Pullulan-C60, and their cholesterol-derivatives. in International Journal of Biological Macromolecules
Elsevier., 165(B), 2541-2549.
https://doi.org/10.1016/j.ijbiomac.2020.10.141

Nešić MD, Dučić T, Liang X, Algarra M, Mi L, Korićanac L, Žakula J, Kop T, Bjelaković M, Mitrović A, Gojgić-Cvijović G, Stepić M, Petković M. SR-FTIR spectro-microscopic interaction study of biochemical changes in HeLa cells induced by Levan-C60, Pullulan-C60, and their cholesterol-derivatives. in International Journal of Biological Macromolecules. 2020;165(B):2541-2549.
doi:10.1016/j.ijbiomac.2020.10.141 .

Nešić, Maja D., Dučić, Tanja, Liang, Xinyue, Algarra, Manuel, Mi, Lan, Korićanac, Lela, Žakula, Jelena, Kop, Tatjana, Bjelaković, Mira, Mitrović, Aleksandra, Gojgić-Cvijović, Gordana, Stepić, Milutin, Petković, Marijana, "SR-FTIR spectro-microscopic interaction study of biochemical changes in HeLa cells induced by Levan-C60, Pullulan-C60, and their cholesterol-derivatives" in International Journal of Biological Macromolecules, 165, no. B (2020):2541-2549,
https://doi.org/10.1016/j.ijbiomac.2020.10.141 . .

TY  - JOUR
AU  - Pavlovic, Radoslav Z.
AU  - Mitrović, Aleksandra
AU  - Coldren, William H.
AU  - Bjelaković, Mira
AU  - Hadad, Christopher M.
AU  - Maslak, Veselin R.
AU  - Milić, Dragana
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2323
AB  - The reactivity of the C-2v-symmetric pentakisadduct of C-60 with azomethine ylides and conjugated dienes was studied experimentally and computationally. This derivative possesses four [6,6] double bonds, each with unique electrophilicity. The Diels-Alder reaction studied is a regiospecific, kinetically and thermodynamically guided [4 + 2] process producing [5:1]-hexaadducts with an octahedral addition pattern. The kinetically controlled Prato reaction gives a mixture of regioisomeric [5:1]-hexaadducts. The synthesis of geometrically well-defined supramolecular architectures may benefit from these new types of highly functionalized [5:1]-hexaadducts.
PB  - American Chemical Society (ACS)
T2  - Journal of Organic Chemistry
T1  - Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60
VL  - 83
IS  - 4
SP  - 2166
EP  - 2172
DO  - 10.1021/acs.joc.7b03083
ER  - 

@article{
author = "Pavlovic, Radoslav Z. and Mitrović, Aleksandra and Coldren, William H. and Bjelaković, Mira and Hadad, Christopher M. and Maslak, Veselin R. and Milić, Dragana",
year = "2018",
abstract = "The reactivity of the C-2v-symmetric pentakisadduct of C-60 with azomethine ylides and conjugated dienes was studied experimentally and computationally. This derivative possesses four [6,6] double bonds, each with unique electrophilicity. The Diels-Alder reaction studied is a regiospecific, kinetically and thermodynamically guided [4 + 2] process producing [5:1]-hexaadducts with an octahedral addition pattern. The kinetically controlled Prato reaction gives a mixture of regioisomeric [5:1]-hexaadducts. The synthesis of geometrically well-defined supramolecular architectures may benefit from these new types of highly functionalized [5:1]-hexaadducts.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Organic Chemistry",
title = "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60",
volume = "83",
number = "4",
pages = "2166-2172",
doi = "10.1021/acs.joc.7b03083"
}

Pavlovic, R. Z., Mitrović, A., Coldren, W. H., Bjelaković, M., Hadad, C. M., Maslak, V. R.,& Milić, D.. (2018). Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60. in Journal of Organic Chemistry
American Chemical Society (ACS)., 83(4), 2166-2172.
https://doi.org/10.1021/acs.joc.7b03083

Pavlovic RZ, Mitrović A, Coldren WH, Bjelaković M, Hadad CM, Maslak VR, Milić D. Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60. in Journal of Organic Chemistry. 2018;83(4):2166-2172.
doi:10.1021/acs.joc.7b03083 .

Pavlovic, Radoslav Z., Mitrović, Aleksandra, Coldren, William H., Bjelaković, Mira, Hadad, Christopher M., Maslak, Veselin R., Milić, Dragana, "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60" in Journal of Organic Chemistry, 83, no. 4 (2018):2166-2172,
https://doi.org/10.1021/acs.joc.7b03083 . .

TY  - DATA
AU  - Pavlovic, Radoslav Z.
AU  - Mitrović, Aleksandra
AU  - Coldren, William H.
AU  - Bjelaković, Mira
AU  - Hadad, Christopher M.
AU  - Maslak, Veselin R.
AU  - Milić, Dragana
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4504
AB  - General information and optimization of reaction conditions, detailed characterization of products 8–15, including their NMR and mass spectra, and computational results (Figures S1–S20 and Table S1)
PB  - American Chemical Society (ACS)
T2  - Journal of Organic Chemistry
T1  - Supporting information for: "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60"
DO  - 10.1021/acs.joc.7b03083.s001
ER  - 

@misc{
author = "Pavlovic, Radoslav Z. and Mitrović, Aleksandra and Coldren, William H. and Bjelaković, Mira and Hadad, Christopher M. and Maslak, Veselin R. and Milić, Dragana",
year = "2018",
abstract = "General information and optimization of reaction conditions, detailed characterization of products 8–15, including their NMR and mass spectra, and computational results (Figures S1–S20 and Table S1)",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Organic Chemistry",
title = "Supporting information for: "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60"",
doi = "10.1021/acs.joc.7b03083.s001"
}

Pavlovic, R. Z., Mitrović, A., Coldren, W. H., Bjelaković, M., Hadad, C. M., Maslak, V. R.,& Milić, D.. (2018). Supporting information for: "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60". in Journal of Organic Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.joc.7b03083.s001

Pavlovic RZ, Mitrović A, Coldren WH, Bjelaković M, Hadad CM, Maslak VR, Milić D. Supporting information for: "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60". in Journal of Organic Chemistry. 2018;.
doi:10.1021/acs.joc.7b03083.s001 .

Pavlovic, Radoslav Z., Mitrović, Aleksandra, Coldren, William H., Bjelaković, Mira, Hadad, Christopher M., Maslak, Veselin R., Milić, Dragana, "Supporting information for: "Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60"" in Journal of Organic Chemistry (2018),
https://doi.org/10.1021/acs.joc.7b03083.s001 . .

TY  - JOUR
AU  - Mitrović, Aleksandra
AU  - Todorović, Nina
AU  - Zekic, Andrijana
AU  - Stanković, Dalibor
AU  - Milić, Dragana
AU  - Maslak, Veselin
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1345
AB  - A series of novel fulleropyrrolidine-phthalimide dyads was synthesized and their electrochemical and self-assembly properties were investigated. Efficient synthesis of acceptor-acceptor dyads was performed under microwave irradiation. Fine-tuning of the second redox potentials in the dyads was achieved by varying the length of the aliphatic spacer (C-2 to C-12) between the fulleropyrrolidine and phthalimide moieties. Shape-shifting and supramolecular polymorphism were observed for these compounds during self-assembly.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Synthesis, Electrochemistry, and Hierarchical Self-Organization of Fulleropyrrolidine-Phthalimide Dyads
IS  - 11
SP  - 2188
EP  - 2193
DO  - 10.1002/ejoc.201201631
ER  - 

@article{
author = "Mitrović, Aleksandra and Todorović, Nina and Zekic, Andrijana and Stanković, Dalibor and Milić, Dragana and Maslak, Veselin",
year = "2013",
abstract = "A series of novel fulleropyrrolidine-phthalimide dyads was synthesized and their electrochemical and self-assembly properties were investigated. Efficient synthesis of acceptor-acceptor dyads was performed under microwave irradiation. Fine-tuning of the second redox potentials in the dyads was achieved by varying the length of the aliphatic spacer (C-2 to C-12) between the fulleropyrrolidine and phthalimide moieties. Shape-shifting and supramolecular polymorphism were observed for these compounds during self-assembly.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Synthesis, Electrochemistry, and Hierarchical Self-Organization of Fulleropyrrolidine-Phthalimide Dyads",
number = "11",
pages = "2188-2193",
doi = "10.1002/ejoc.201201631"
}

Mitrović, A., Todorović, N., Zekic, A., Stanković, D., Milić, D.,& Maslak, V.. (2013). Synthesis, Electrochemistry, and Hierarchical Self-Organization of Fulleropyrrolidine-Phthalimide Dyads. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(11), 2188-2193.
https://doi.org/10.1002/ejoc.201201631

Mitrović A, Todorović N, Zekic A, Stanković D, Milić D, Maslak V. Synthesis, Electrochemistry, and Hierarchical Self-Organization of Fulleropyrrolidine-Phthalimide Dyads. in European Journal of Organic Chemistry. 2013;(11):2188-2193.
doi:10.1002/ejoc.201201631 .

Mitrović, Aleksandra, Todorović, Nina, Zekic, Andrijana, Stanković, Dalibor, Milić, Dragana, Maslak, Veselin, "Synthesis, Electrochemistry, and Hierarchical Self-Organization of Fulleropyrrolidine-Phthalimide Dyads" in European Journal of Organic Chemistry, no. 11 (2013):2188-2193,
https://doi.org/10.1002/ejoc.201201631 . .