TY  - JOUR
AU  - Skaro Bogojevic, S
AU  - Perminova, D
AU  - Jaksic, J
AU  - Milcic, M
AU  - Medakovic, V
AU  - Milovanovic, J
AU  - Nikodinovic-Runic, J
AU  - Maslak, V
PY  - 2024
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6476
AB  - Poly(ethylene terephthalate) (PET) is widely used material in the healthcare due to its mechanical properties including resistance to chemicals and abrasion. However, it is susceptible to bacterial attachment and contamination. This study addresses some newly designed model compounds of PET with antimicrobial properties that could potentially be incorporated into PET materials. All compounds were synthesized for the first time by labeling an integral part of PET with chromophores in the form of esters of cinnamic and ferulic acids. After complete structural characterization, the effect of new compounds on microbial growth and communication (quorum sensing, QS) was analyzed and further investigated using molecular docking. The obtained results indicate that the introduction of chromophores that have one part of cinnamic acid enriched with a methoxy functional group in them acts as QS modulators. Moreover, compounds exhibited dose-dependent selectivity toward QS signaling pathways and the highest tested concentration of compounds showed Pseudomonas Quinolone Signal (PQS) inhibitory activity suggesting that these compounds have a potential effect on pyocyanin production. Docking studies demonstrated that compounds hold binding power to all four QS protein targets (LuxP, periplasmatic protein that binds AI-2 inducer and forms a complex able to transduce the autoinducer signal, RhIR protein that is a key QS transcriptional regulator that activates the genes involved in the synthesis of rhamnolipids and pyocyanin, AbaI protein that has a role in QS signal transduction, and LasR protein which is a key QS transcriptional regulator that activates transcription of genes coding for some virulence-associated traits) while the highest binding strength is observed with compounds 2 and 6 containing single cinnamic acid fragment, suggesting their further biomedical application.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Novel cinnamic acid-based PET derivatives as quorum sensing modulators
VL  - 1300
SP  - 137291
DO  - 10.1016/j.molstruc.2023.137291
ER  - 

@article{
author = "Skaro Bogojevic, S and Perminova, D and Jaksic, J and Milcic, M and Medakovic, V and Milovanovic, J and Nikodinovic-Runic, J and Maslak, V",
year = "2024",
abstract = "Poly(ethylene terephthalate) (PET) is widely used material in the healthcare due to its mechanical properties including resistance to chemicals and abrasion. However, it is susceptible to bacterial attachment and contamination. This study addresses some newly designed model compounds of PET with antimicrobial properties that could potentially be incorporated into PET materials. All compounds were synthesized for the first time by labeling an integral part of PET with chromophores in the form of esters of cinnamic and ferulic acids. After complete structural characterization, the effect of new compounds on microbial growth and communication (quorum sensing, QS) was analyzed and further investigated using molecular docking. The obtained results indicate that the introduction of chromophores that have one part of cinnamic acid enriched with a methoxy functional group in them acts as QS modulators. Moreover, compounds exhibited dose-dependent selectivity toward QS signaling pathways and the highest tested concentration of compounds showed Pseudomonas Quinolone Signal (PQS) inhibitory activity suggesting that these compounds have a potential effect on pyocyanin production. Docking studies demonstrated that compounds hold binding power to all four QS protein targets (LuxP, periplasmatic protein that binds AI-2 inducer and forms a complex able to transduce the autoinducer signal, RhIR protein that is a key QS transcriptional regulator that activates the genes involved in the synthesis of rhamnolipids and pyocyanin, AbaI protein that has a role in QS signal transduction, and LasR protein which is a key QS transcriptional regulator that activates transcription of genes coding for some virulence-associated traits) while the highest binding strength is observed with compounds 2 and 6 containing single cinnamic acid fragment, suggesting their further biomedical application.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Novel cinnamic acid-based PET derivatives as quorum sensing modulators",
volume = "1300",
pages = "137291",
doi = "10.1016/j.molstruc.2023.137291"
}

Skaro Bogojevic, S., Perminova, D., Jaksic, J., Milcic, M., Medakovic, V., Milovanovic, J., Nikodinovic-Runic, J.,& Maslak, V.. (2024). Novel cinnamic acid-based PET derivatives as quorum sensing modulators. in Journal of Molecular Structure
Elsevier., 1300, 137291.
https://doi.org/10.1016/j.molstruc.2023.137291

Skaro Bogojevic S, Perminova D, Jaksic J, Milcic M, Medakovic V, Milovanovic J, Nikodinovic-Runic J, Maslak V. Novel cinnamic acid-based PET derivatives as quorum sensing modulators. in Journal of Molecular Structure. 2024;1300:137291.
doi:10.1016/j.molstruc.2023.137291 .

Skaro Bogojevic, S, Perminova, D, Jaksic, J, Milcic, M, Medakovic, V, Milovanovic, J, Nikodinovic-Runic, J, Maslak, V, "Novel cinnamic acid-based PET derivatives as quorum sensing modulators" in Journal of Molecular Structure, 1300 (2024):137291,
https://doi.org/10.1016/j.molstruc.2023.137291 . .

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Milinković, Evgenija
AU  - Cvetanović, Katarina
AU  - Tokić Vujošević, Zorana
AU  - Jovanov, Vladislav
AU  - Mitrović, Aleksandra D.
AU  - Maslak, Veselin
PY  - 2024
UR  - https://pubs.rsc.org/en/content/articlelanding/2024/cp/d3cp04322c
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6422
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 we respecifically designed to enhance solubility and interaction with the substrate, fluorine-dopedtinoxide (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 in sights into charge transfer properties at the electrode/electrolyte interface, making the compounds attractive candidates for electron transport layers (ETLs) in PSCs.
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 Tokić Vujošević, Zorana and Jovanov, Vladislav and Mitrović, Aleksandra D. and Maslak, Veselin",
year = "2024",
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 we respecifically designed to enhance solubility and interaction with the substrate, fluorine-dopedtinoxide (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 in sights into charge transfer properties at the electrode/electrolyte interface, making the compounds attractive candidates for electron transport layers (ETLs) in PSCs.",
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., Tokić Vujošević, Z., Jovanov, V., Mitrović, A. D.,& Maslak, V.. (2024). Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study. in Physical Chemistry Chemical Physics, 26(1), 517-523.
https://doi.org/10.1039/D3CP04322C

Jakšić J, Milinković E, Cvetanović K, Tokić Vujošević Z, Jovanov V, Mitrović AD, Maslak V. Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study. in Physical Chemistry Chemical Physics. 2024;26(1):517-523.
doi:10.1039/D3CP04322C .

Jakšić, Jovana, Milinković, Evgenija, Cvetanović, Katarina, Tokić Vujošević, Zorana, Jovanov, Vladislav, Mitrović, Aleksandra D., Maslak, Veselin, "Exploring fullerene derivatives for optoelectronic applications: synthesis and characterization study" in Physical Chemistry Chemical Physics, 26, no. 1 (2024):517-523,
https://doi.org/10.1039/D3CP04322C . .

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Solymosi, Iris
AU  - Hirsch, Andreas
AU  - Pérez-Ojeda, M. Eugenia
AU  - Mitrović, Aleksandra D.
AU  - Maslak, Veselin
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6272
AB  - The synthesis and characterization of four dumbbell-shaped fullerene molecules connected by isosorbide and isomannide moieties is presented. Additionally, their electrochemical behavior and their ability to form complexes with [10]cycloparaphenylene ([10]CPP) were investigated. The cyclic voltammetry (CV) results of the fullerene dumbbells demonstrate a high electron affinity, indicating their strong interaction with electron-donating counterparts such as carbon nanorings, which possess complementary charge and shape properties. To study the thermodynamic and kinetic parameters of complexation, isothermal titration calorimetry (ITC) was employed. NMR titration experiments provided further insights into the binding stoichiometries. Two distinct approaches were utilized to create bridged structures: one based on cyclopropane and the other based on furan. Regardless of the type of linker used, all derivatives formed conventional 2 : 1 complexes denoted as [10]CPP2 ⊃C60derivative . However, the methano-dumbbell molecules exhibited distinct binding behavior, resulting in the formation of mono- and bis-pseudorotaxanes, as well as oligomers (polymers). The formation of linear polymers holds significant potential for applications in solar energy conversion processes.
PB  - John Wiley and Sons Inc
T2  - Chemistry (Weinheim an Der Bergstrasse, Germany)
T1  - Sugar-Bridged Fullerene Dumbbells and Their Interaction with the [10]Cycloparaphenylene Nanoring
VL  - 29
IS  - 44
SP  - e202301061
DO  - 10.1002/chem.202301061
ER  - 

@article{
author = "Jakšić, Jovana and Solymosi, Iris and Hirsch, Andreas and Pérez-Ojeda, M. Eugenia and Mitrović, Aleksandra D. and Maslak, Veselin",
year = "2023",
abstract = "The synthesis and characterization of four dumbbell-shaped fullerene molecules connected by isosorbide and isomannide moieties is presented. Additionally, their electrochemical behavior and their ability to form complexes with [10]cycloparaphenylene ([10]CPP) were investigated. The cyclic voltammetry (CV) results of the fullerene dumbbells demonstrate a high electron affinity, indicating their strong interaction with electron-donating counterparts such as carbon nanorings, which possess complementary charge and shape properties. To study the thermodynamic and kinetic parameters of complexation, isothermal titration calorimetry (ITC) was employed. NMR titration experiments provided further insights into the binding stoichiometries. Two distinct approaches were utilized to create bridged structures: one based on cyclopropane and the other based on furan. Regardless of the type of linker used, all derivatives formed conventional 2 : 1 complexes denoted as [10]CPP2 ⊃C60derivative . However, the methano-dumbbell molecules exhibited distinct binding behavior, resulting in the formation of mono- and bis-pseudorotaxanes, as well as oligomers (polymers). The formation of linear polymers holds significant potential for applications in solar energy conversion processes.",
publisher = "John Wiley and Sons Inc",
journal = "Chemistry (Weinheim an Der Bergstrasse, Germany)",
title = "Sugar-Bridged Fullerene Dumbbells and Their Interaction with the [10]Cycloparaphenylene Nanoring",
volume = "29",
number = "44",
pages = "e202301061",
doi = "10.1002/chem.202301061"
}

Jakšić, J., Solymosi, I., Hirsch, A., Pérez-Ojeda, M. E., Mitrović, A. D.,& Maslak, V.. (2023). Sugar-Bridged Fullerene Dumbbells and Their Interaction with the [10]Cycloparaphenylene Nanoring. in Chemistry (Weinheim an Der Bergstrasse, Germany)
John Wiley and Sons Inc., 29(44), e202301061.
https://doi.org/10.1002/chem.202301061

Jakšić J, Solymosi I, Hirsch A, Pérez-Ojeda ME, Mitrović AD, Maslak V. Sugar-Bridged Fullerene Dumbbells and Their Interaction with the [10]Cycloparaphenylene Nanoring. in Chemistry (Weinheim an Der Bergstrasse, Germany). 2023;29(44):e202301061.
doi:10.1002/chem.202301061 .

Jakšić, Jovana, Solymosi, Iris, Hirsch, Andreas, Pérez-Ojeda, M. Eugenia, Mitrović, Aleksandra D., Maslak, Veselin, "Sugar-Bridged Fullerene Dumbbells and Their Interaction with the [10]Cycloparaphenylene Nanoring" in Chemistry (Weinheim an Der Bergstrasse, Germany), 29, no. 44 (2023):e202301061,
https://doi.org/10.1002/chem.202301061 . .

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Mitrović, Aleksandra D.
AU  - Tokić-Vujošević, Zorana
AU  - Milčić, Miloš K.
AU  - Maslak, Veselin
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4714
AB  - In this study, β-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and π-electron delocalization between methano and furano fullerenes.
PB  - Royal Society of Chemistry
T2  - RSC Advances
T1  - Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60
VL  - 11
IS  - 47
SP  - 29426
EP  - 29432
DO  - 10.1039/D1RA03944J
ER  - 

@article{
author = "Jakšić, Jovana and Mitrović, Aleksandra D. and Tokić-Vujošević, Zorana and Milčić, Miloš K. and Maslak, Veselin",
year = "2021",
abstract = "In this study, β-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and π-electron delocalization between methano and furano fullerenes.",
publisher = "Royal Society of Chemistry",
journal = "RSC Advances",
title = "Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60",
volume = "11",
number = "47",
pages = "29426-29432",
doi = "10.1039/D1RA03944J"
}

Jakšić, J., Mitrović, A. D., Tokić-Vujošević, Z., Milčić, M. K.,& Maslak, V.. (2021). Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60. in RSC Advances
Royal Society of Chemistry., 11(47), 29426-29432.
https://doi.org/10.1039/D1RA03944J

Jakšić J, Mitrović AD, Tokić-Vujošević Z, Milčić MK, Maslak V. Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60. in RSC Advances. 2021;11(47):29426-29432.
doi:10.1039/D1RA03944J .

Jakšić, Jovana, Mitrović, Aleksandra D., Tokić-Vujošević, Zorana, Milčić, Miloš K., Maslak, Veselin, "Selective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60" in RSC Advances, 11, no. 47 (2021):29426-29432,
https://doi.org/10.1039/D1RA03944J . .

TY  - DATA
AU  - Jakšić, Jovana
AU  - Mitrović, Aleksandra D.
AU  - Tokić-Vujošević, Zorana
AU  - Milčić, Miloš K.
AU  - Maslak, Veselin
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4717
PB  - Royal Society of Chemistry
T2  - RSC Advances
T1  - Supplementary data for the article: Jakšić, J.; Mitrović, A.; Vujošević, Z. T.; Milčić, M.; Maslak, V. Selective Formation of Dihydrofuran Fused [60] Fullerene Derivatives by TEMPO Mediated [3 + 2] Cycloaddition of Medium Chain β-Keto Esters to C60. RSC Adv. 2021, 11 (47), 29426–29432. https://doi.org/10.1039/D1RA03944J.
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4717
ER  - 

@misc{
author = "Jakšić, Jovana and Mitrović, Aleksandra D. and Tokić-Vujošević, Zorana and Milčić, Miloš K. and Maslak, Veselin",
year = "2021",
publisher = "Royal Society of Chemistry",
journal = "RSC Advances",
title = "Supplementary data for the article: Jakšić, J.; Mitrović, A.; Vujošević, Z. T.; Milčić, M.; Maslak, V. Selective Formation of Dihydrofuran Fused [60] Fullerene Derivatives by TEMPO Mediated [3 + 2] Cycloaddition of Medium Chain β-Keto Esters to C60. RSC Adv. 2021, 11 (47), 29426–29432. https://doi.org/10.1039/D1RA03944J.",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4717"
}

Jakšić, J., Mitrović, A. D., Tokić-Vujošević, Z., Milčić, M. K.,& Maslak, V.. (2021). Supplementary data for the article: Jakšić, J.; Mitrović, A.; Vujošević, Z. T.; Milčić, M.; Maslak, V. Selective Formation of Dihydrofuran Fused [60] Fullerene Derivatives by TEMPO Mediated [3 + 2] Cycloaddition of Medium Chain β-Keto Esters to C60. RSC Adv. 2021, 11 (47), 29426–29432. https://doi.org/10.1039/D1RA03944J.. in RSC Advances
Royal Society of Chemistry..
https://hdl.handle.net/21.15107/rcub_cherry_4717

Jakšić J, Mitrović AD, Tokić-Vujošević Z, Milčić MK, Maslak V. Supplementary data for the article: Jakšić, J.; Mitrović, A.; Vujošević, Z. T.; Milčić, M.; Maslak, V. Selective Formation of Dihydrofuran Fused [60] Fullerene Derivatives by TEMPO Mediated [3 + 2] Cycloaddition of Medium Chain β-Keto Esters to C60. RSC Adv. 2021, 11 (47), 29426–29432. https://doi.org/10.1039/D1RA03944J.. in RSC Advances. 2021;.
https://hdl.handle.net/21.15107/rcub_cherry_4717 .

Jakšić, Jovana, Mitrović, Aleksandra D., Tokić-Vujošević, Zorana, Milčić, Miloš K., Maslak, Veselin, "Supplementary data for the article: Jakšić, J.; Mitrović, A.; Vujošević, Z. T.; Milčić, M.; Maslak, V. Selective Formation of Dihydrofuran Fused [60] Fullerene Derivatives by TEMPO Mediated [3 + 2] Cycloaddition of Medium Chain β-Keto Esters to C60. RSC Adv. 2021, 11 (47), 29426–29432. https://doi.org/10.1039/D1RA03944J." in RSC Advances (2021),
https://hdl.handle.net/21.15107/rcub_cherry_4717 .