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Szabo, Zoltan, Associate professorORCID iD iconorcid.org/0000-0002-7552-1076
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Publications (10 of 89) Show all publications
Karalius, A., Qi, Y., Ayinla, M., Szabó, Z. & Ramström, O. (2024). Interdependent Dynamic Nitroaldol and Boronic Ester Reactions for Complex Dynamers of Different Topologies. Chemistry - A European Journal, 30(63), Article ID e202402409.
Open this publication in new window or tab >>Interdependent Dynamic Nitroaldol and Boronic Ester Reactions for Complex Dynamers of Different Topologies
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2024 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 30, no 63, article id e202402409Article in journal (Refereed) Published
Abstract [en]

Complex dynamic systems displaying interdependency between nitroaldol and boronic ester reactions have been demonstrated. Nitroalkane-1,3-diols, generated by the nitroaldol reaction, were susceptible to ester formation with different boronic acids in aprotic solvents, whereas hydrolysis of the esters occurred in the presence of water. The boronic ester formation led to significant stabilization of the nitroaldol adducts under basic conditions. The use of bifunctional building blocks was furthermore established, allowing for main chain nitroaldol-boronate dynamers as well as complex network dynamers with distinct topologies. The shape and rigidity of the resulting dynamers showed an apparent dependency on the configuration of the boronic acids.

Place, publisher, year, edition, pages
Wiley, 2024
Keywords
Boronate, Dynamer, Dynamic covalent, Nitroaldol, Topology
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-366501 (URN)10.1002/chem.202402409 (DOI)001339776900001 ()39183180 (PubMedID)2-s2.0-85207152228 (Scopus ID)
Note

QC 20250708

Available from: 2025-07-08 Created: 2025-07-08 Last updated: 2025-07-08Bibliographically approved
Proietti, G., Axelsson, A., Capezza, A. J., Todarwal, Y., Kuzmin, J., Linares, M., . . . Dinér, P. (2024). Ultralight aerogels via supramolecular polymerization of a new chiral perfluoropyridine-based sulfonimidamide organogelator. Nanoscale, 16(15), 7603-7611
Open this publication in new window or tab >>Ultralight aerogels via supramolecular polymerization of a new chiral perfluoropyridine-based sulfonimidamide organogelator
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2024 (English)In: Nanoscale, ISSN 2040-3364, E-ISSN 2040-3372, Vol. 16, no 15, p. 7603-7611Article in journal (Refereed) Published
Abstract [en]

Chiral and enantiopure perfluorinated sulfonimidamides act as low-molecular weight gelators at low critical gelation concentration (<1 mg mL-1) via supramolecular polymerization in nonpolar organic solvents and more heterogenic mixtures, such as biodiesel and oil. Freeze-drying of the organogel leads to ultralight aerogel with extremely low density (1 mg mL-1). The gelation is driven by hydrogen bonding resulting in a helical molecular ordering and unique fibre assemblies as confirmed by scanning electron microscopy, CD spectroscopy, and computational modeling of the supramolecular structure.

Place, publisher, year, edition, pages
Royal Society of Chemistry (RSC), 2024
National Category
Chemical Sciences
Research subject
Chemistry
Identifiers
urn:nbn:se:kth:diva-347069 (URN)10.1039/d3nr06460c (DOI)001188638600001 ()38512219 (PubMedID)2-s2.0-85188741705 (Scopus ID)
Funder
Carl Tryggers foundation , CTS:19-80Swedish Research Council, 2023-04482Swedish Research Council, 2023-5171Bo Rydin Foundation for Scientific Research, F 30/19Carl Tryggers foundation , CTS:19-80Swedish Research Council, 2023-04482Swedish Research Council, 2023-5171Bo Rydin Foundation for Scientific Research, F 30/19
Note

QC 20240603

Available from: 2024-05-31 Created: 2024-05-31 Last updated: 2024-06-03Bibliographically approved
Liu, T., Zhan, S., Shen, N., Wang, L., Szabo, Z., Yang, H., . . . Sun, L. (2023). Bioinspired Active Site with a Coordination-Adaptive Organosulfonate Ligand for Catalytic Water Oxidation at Neutral pH. Journal of the American Chemical Society, 145(21), 11818-11828
Open this publication in new window or tab >>Bioinspired Active Site with a Coordination-Adaptive Organosulfonate Ligand for Catalytic Water Oxidation at Neutral pH
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2023 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 145, no 21, p. 11818-11828Article in journal (Refereed) Published
Abstract [en]

Many enzymes use adaptive frameworks to preorganize substrates, accommodate various structural and electronic demands of intermediates, and accelerate related catalysis. Inspired by biological systems, a Ru-based molecular water oxidation catalyst containing a configurationally labile ligand [2,2′:6′,2″-terpyridine]-6,6″-disulfonate was designed to mimic enzymatic framework, in which the sulfonate coordination is highly flexible and functions as both an electron donor to stabilize high-valent Ru and a proton acceptor to accelerate water dissociation, thus boosting the catalytic water oxidation performance thermodynamically and kinetically. The combination of single-crystal X-ray analysis, various temperature NMR, electrochemical techniques, and DFT calculations was utilized to investigate the fundamental role of the self-adaptive ligand, demonstrating that the on-demand configurational changes give rise to fast catalytic kinetics with a turnover frequency (TOF) over 2000 s–1, which is compared to oxygen-evolving complex (OEC) in natural photosynthesis. 

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2023
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-327110 (URN)10.1021/jacs.3c03415 (DOI)001011072400001 ()37196315 (PubMedID)2-s2.0-85160751257 (Scopus ID)
Funder
Swedish Research Council, 2017-00935
Note

QC 20230523

Available from: 2023-05-19 Created: 2023-05-19 Last updated: 2024-03-15Bibliographically approved
Li, J., Szabo, Z. & Jonsson, M. (2022). Stability of Studtite in Saline Solution: Identification of Uranyl- Peroxo-Halo Complex. Inorganic Chemistry, 61(22), 8455-8466
Open this publication in new window or tab >>Stability of Studtite in Saline Solution: Identification of Uranyl- Peroxo-Halo Complex
2022 (English)In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 61, no 22, p. 8455-8466Article in journal (Refereed) Published
Abstract [en]

Hydrogen peroxide is produced upon radiolysis of water and has been shown to be the main oxidant driving oxidative dissolution of UO2-based nuclear fuel under geological repository conditions. While the overall mechanism and speciation are well known for granitic groundwaters, considerably less is known for saline waters of relevance in rock salt or during emergency cooling of reactors using seawater. In this work, the ternary uranyl-peroxo-chioro and uranyl-peroxo-bromo complexes were identified using IR, Raman, and nuclear magnetic resonance (NMR) spectroscopy. Based on Raman spectra, the estimated stability constants for the identified uranyl-peroxo-chloro ((UO2)(O-2)(Cl)(H2O)(2)(-)) and uranyl-peroxo-bromo ((UO2)(O-2)(Br)(H2O)(2)(-)) complexes are 0.17 and 0.04, respectively, at ionic strength approximate to 45 mol/ L. It was found that the uranyl-peroxo-chloro complex is more stable than the uranyi-peroxo- bromo complex, which transforms into studtite at high uranyl and H2O2 concentrations. Studtitc is also found to be dissolved at a high ionic strength, implying that this may not be a stable solid phase under very saline conditions. The uranyl-peroxo-bromo complex was shown to facilitate H2O2 decomposition via a mechanism involving reactive intermediates.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2022
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-315146 (URN)10.1021/acs.inorgchem.2c00233 (DOI)000809419100008 ()35608075 (PubMedID)2-s2.0-85131701498 (Scopus ID)
Note

QC 20220701

Available from: 2022-07-01 Created: 2022-07-01 Last updated: 2023-09-04Bibliographically approved
Li, J., Szabo, Z. & Jonsson, M. (2021). Meta-studtite stability in aqueous solutions. Impact of HCO3-, H2O2and ionizing radiation on dissolution and speciation. Dalton Transactions, 50(19), 6568-6577
Open this publication in new window or tab >>Meta-studtite stability in aqueous solutions. Impact of HCO3-, H2O2and ionizing radiation on dissolution and speciation
2021 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 50, no 19, p. 6568-6577Article in journal (Refereed) Published
Abstract [en]

Two uranyl peroxides meta-studtite and studtite exist in nature and can form as alteration phases on the surface of spent nuclear fuel upon water intrusion in a geological repository. Meta-studtite and studtite have very low solubility and could therefore reduce the reactivity of spent nuclear fuel toward radiolytic oxidants. This would inhibit the dissolution of the fuel matrix and thereby also the spreading of radionuclides. It is therefore important to investigate the stability of meta-studtite and studtite under conditions that may influence their stability. In the present work, we have studied the dissolution kinetics of meta-studtite in aqueous solution containing 10 mM HCO3-. In addition, the influence of the added H2O2 and the impact of γ-irradiation on the dissolution kinetics of meta-studtite were studied. The results are compared to previously published data for studtite studied under the same conditions. 13C NMR experiments were performed to identify the species present in aqueous solution (i.e., carbonate containing complexes). The speciation studies are compared to calculations based on published equilibrium constants. In addition to the dissolution experiments, experiments focussing on the stability of H2O2 in aqueous solutions containing UO22+ and HCO3- were conducted. The rationale for this is that H2O2 was consumed relatively fast in some of the dissolution experiments.

Place, publisher, year, edition, pages
Royal Society of Chemistry (RSC), 2021
National Category
Inorganic Chemistry
Identifiers
urn:nbn:se:kth:diva-309962 (URN)10.1039/d1dt00436k (DOI)000642606500001 ()33890958 (PubMedID)2-s2.0-85106191809 (Scopus ID)
Note

QC 20220316

Available from: 2022-03-16 Created: 2022-03-16 Last updated: 2024-03-15Bibliographically approved
Marton, J., Sipos, A., Henriksen, G., Cumming, P., Berenyi, S., Schmitt, B. M. & Szabo, Z. (2021). NMR Analysis of a Series of 6,14-Ethenomorphinan Derivatives as PET Precursors and Reference Substances**. ChemistrySelect, 6(24), 5994-6005
Open this publication in new window or tab >>NMR Analysis of a Series of 6,14-Ethenomorphinan Derivatives as PET Precursors and Reference Substances**
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2021 (English)In: ChemistrySelect, E-ISSN 2365-6549, Vol. 6, no 24, p. 5994-6005Article in journal (Refereed) Published
Abstract [en]

The new semisynthetic oripavine derivative 3-O-trityl-6-O-desmethyl-dihydroetorphine was synthesized from the poppy alkaloid thebaine in a six-step procedure. This compound can be applied as precursor for the radiosynthesis of [6-O-methyl-C-11]-dihydroetorphine ([C-11]DHE). We present a detailed description of H-1 and C-13 NMR data of reference standards and precursors for [6-O-methyl-C-11]- and [6-O-(2-[F-18]fluoroethyl]orvinols. This includes the complete assignment for 19 oripavine derivatives examined in 1D and 2D NMR experiments. We also investigated the molecular basis for regioselectivity of fluoroalkylation of 3-O-trityl-6-O-desmethyl-phenethyl-orvinol (TDPEO) using computational methods.

Place, publisher, year, edition, pages
Wiley, 2021
Keywords
dihydroetorphine, 6, 14-ethenomorphinan, Grignard reaction, PET precursor, NMR spectroscopy
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-299697 (URN)10.1002/slct.202101597 (DOI)000674320500020 ()2-s2.0-85110476149 (Scopus ID)
Note

QC 20210816

Available from: 2021-08-16 Created: 2021-08-16 Last updated: 2024-08-30Bibliographically approved
Karalius, A., Zhang, Y., Kravchenko, O., Elofsson, U., Szabo, Z., Yan, M. & Ramström, O. (2020). Formation and Out‐of‐Equilibrium, High/Low State Switching of a Nitroaldol Dynamer in Neutral Aqueous Media. Angewandte Chemie International Edition, 59(9), 3434-3438
Open this publication in new window or tab >>Formation and Out‐of‐Equilibrium, High/Low State Switching of a Nitroaldol Dynamer in Neutral Aqueous Media
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2020 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 59, no 9, p. 3434-3438Article in journal (Refereed) Published
Place, publisher, year, edition, pages
Wiley, 2020
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-267001 (URN)10.1002/anie.201911706 (DOI)000508501500001 ()31863678 (PubMedID)2-s2.0-85078789872 (Scopus ID)
Note

QC 20200203

Available from: 2020-01-29 Created: 2020-01-29 Last updated: 2022-06-26Bibliographically approved
Villo, P., Dalla-Santa, O., Szabo, Z. & Lundberg, H. (2020). Kinetic Analysis as an Optimization Tool for Catalytic Esterification with a Moisture-Tolerant Zirconium Complex. Journal of Organic Chemistry, 85(11), 6959-6969
Open this publication in new window or tab >>Kinetic Analysis as an Optimization Tool for Catalytic Esterification with a Moisture-Tolerant Zirconium Complex
2020 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 85, no 11, p. 6959-6969Article in journal (Refereed) Published
Abstract [en]

This work describes the use of kinetics as a tool for rational optimization of an esterification process with down to equimolar ratios of reagents using a recyclable commercially available zirconocene complex in catalytic amounts. In contrast to previously reported group IV metal-catalyzed esterification protocols, the work presented herein circumvents the use of water scavengers and perfluorooctane sulfonate (PFOS) ligands. Insights into the operating mechanism are presented.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC, 2020
National Category
Environmental Sciences
Identifiers
urn:nbn:se:kth:diva-277650 (URN)10.1021/acs.joc.0c00235 (DOI)000538764000013 ()32352291 (PubMedID)2-s2.0-85086650824 (Scopus ID)
Note

QC 20200804

Available from: 2020-08-04 Created: 2020-08-04 Last updated: 2024-03-18Bibliographically approved
Szucs, E., Marton, J., Szabo, Z., Hosztafi, S., Kekesi, G., Tuboly, G., . . . Otvos, F. (2020). Synthesis, biochemical, pharmacological characterization and in silico profile modelling of highly potent opioid orvinol and thevinol derivatives. European Journal of Medicinal Chemistry, 191, Article ID UNSP 112145.
Open this publication in new window or tab >>Synthesis, biochemical, pharmacological characterization and in silico profile modelling of highly potent opioid orvinol and thevinol derivatives
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2020 (English)In: European Journal of Medicinal Chemistry, ISSN 0223-5234, E-ISSN 1768-3254, Vol. 191, article id UNSP 112145Article in journal (Refereed) Published
Abstract [en]

Morphine and its derivatives play inevitably important role in the m-opioid receptor (MOR) targeted antinociception. A structure-activity relationship study is presented for novel and known orvinol and thevinol derivatives with varying 3-O, 6-O, 17-N and 20-alkyl substitutions starting from agonists, antagonists and partial agonists. In vitro competition binding experiments with [H-3]DAMGO showed low subnanomolar affinity to MOR. Generally, 6-O-demethylation increased the affinity toward MOR and decreased the efficacy changing the pharmacological profile in some cases. In vivo tests in osteoarthritis inflammation model showed significant antiallodynic effects of thevinol derivatives while orvinol derivatives did not. The pharmacological character was modelled by computational docking to both active and inactive state models of MOR. Docking energy difference for the two states separates agonists and antagonists well while partial agonists overlapped with them. An interaction pattern of the ligands, involving the interacting receptor atoms, showed more efficient separation of the pharmacological profiles. In rats, thevinol derivatives showed antiallodynic effect in vivo. The orvinol derivatives, except for 6-O-desmethyl-dihydroetorfin (2c), did not show antiallodynic effect.

Place, publisher, year, edition, pages
ELSEVIER, 2020
Keywords
G-protein, Efficacy, Binding, Mu-opioid, Osteoarthritis inflammation model, Interaction fingerprint, 6, 14-Ethenomorphinan derivatives
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-272810 (URN)10.1016/j.ejmech.2020.112145 (DOI)000523562700022 ()32092588 (PubMedID)2-s2.0-85079647995 (Scopus ID)
Note

QC 20200429

Available from: 2020-04-29 Created: 2020-04-29 Last updated: 2022-06-26Bibliographically approved
Mueller, K., Szabo, Z. & Zhang, X. (2019). Interdisciplinary Round-Robin Test on Molecular Spectroscopy of the U(VI) Acetate System. ACS Omega, 4(5), 8167-8177
Open this publication in new window or tab >>Interdisciplinary Round-Robin Test on Molecular Spectroscopy of the U(VI) Acetate System
2019 (English)In: ACS Omega, E-ISSN 2470-1343, Vol. 4, no 5, p. 8167-8177Article in journal (Refereed) Published
Abstract [en]

A comprehensive molecular analysis of a simple aqueous complexing system. U(VI) acetate. selected to be independently investigated by various spectroscopic (vibrational, luminescence, X-ray absorption, and nuclear magnetic resonance spectroscopy) and quantum chemical methods was achieved by an international round-robin test (RRT). Twenty laboratories from six different countries with a focus on actinide or geochemical research participated and contributed to this scientific endeavor. The outcomes of this RRT were considered on two levels of complexity: first, within each technical discipline, conformities as well as discrepancies of the results and their sources were evaluated. The raw data from the different experimental approaches were found to be generally consistent. In particular, for complex setups such as accelerator-based X-ray absorption spectroscopy, the agreement between the raw data was high. By contrast, luminescence spectroscopic data turned out to be strongly related to the chosen acquisition parameters. Second, the potentials and limitations of coupling various spectroscopic and theoretical approaches for the comprehensive study of actinide molecular complexes were assessed. Previous spectroscopic data from the literature were revised and the benchmark data on the U(VI) acetate system provided an unambiguous molecular interpretation based on the correlation of spectroscopic and theoretical results. The multimethodologic approach and the conclusions drawn address not only important aspects of actinide spectroscopy but particularly general aspects of modern molecular analytical chemistry.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2019
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-254106 (URN)10.1021/acsomega.9b00164 (DOI)000470094000030 ()31459906 (PubMedID)2-s2.0-85065335242 (Scopus ID)
Note

QC 20190624

Available from: 2019-06-24 Created: 2019-06-24 Last updated: 2022-06-26Bibliographically approved
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ORCID iD: ORCID iD iconorcid.org/0000-0002-7552-1076

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