Dr. Krunoslav Užarević
HR-10000 Zagreb
Croatia
Projects
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2019-2021 European Social Fund and Croatian Science Foundation – 300 000 E “Mechanochemical and solvent-free strategies towards functional porous materials with advanced physicochemical and catalytic properties”.
2016-2019 Croatian Science Foundation Starting Grant (duration 3 years). 150000 E (PI)
2019 Grant of Croatian Academy of Sciences and Arts for the organization of an international scientific meeting (Solid-State Science and Research 2019). (PI)
2019- DESY synchrotron grant: Real-time and in situ monitoring of the mechanical stress and amorphization processes in relevant metal-organic frameworks (PI)
2016- DESY synchrotron grant: Real-time and in situ monitoring of mechanochemical reaction mechanisms, (PI Tomislav Friščić)
2015-2017 Bilateral Project “Simultaneous synchrotron X-ray powder diffraction and Raman spectroscopy monitoring of mechanochemical reactions in situ and in real-time”; German partner dr. Franziska Emmerling, BAM institute, Berlin (duration 2 years). (PI)
2014 Grant of Croatian Academy of Sciences and Arts for the project “Development of Raman spectroscopic methodology for direct and in situ monitoring of mechanochemical reactions “.(PI)
Awards and Achievements
2017 - Regional Editor for Molecular Crystals and Liquid Crystals journal, Taylor&Francis
2014-2015 NewFelPro Scholarship - Postdoctoral Researcher at McGill University, Montreal
2013 - Award for distinguished scientific contribution from RB Institute
2013-2015 - Awards from Division of Physical Chemistry, RB Institute, for distinguished scientific publications.
2009 - "National award for excellence" obtained from Croatian Ministry of Science, Sports and Education.
Classes
More than 3000 working hours teaching laboratory and seminal courses in General and Inorganic Chemistry for students in chemistry, biology, geology and physics.
2019 Supervision of a postdoc student – Dr. Dijana Saftić – mechanochemical organic synthesis
2017-present Supervision of a postdoc student – Dr. Bahar Karadeniz – mechanochemical synthesis of MOF materials
2018-present Mentor to a Ph. D. student in the field of mechanochemical prebiotic synthesis
2014-2018 Mentor of a Ph. D. student in the field of organic mechanochemical synthesis. Ruđer Bošković Institute, Zagreb, Croatia. Thesis defended in 2018, June 27th. Thesis title: DEVELOPMENT OF MECHANOCHEMICAL SYNTHESIS OF AMIDES, UREAS AND TRIAZOLES
2002 – 2012: Mentoring the experimental work and writing of the Thesis for 10 graduate students in their obtaining of a Master's degree. Faculty of Science, University of Zagreb, Croatia
2009-2012 Work from five undergrad students published in four scientific papers: Cryst. Growth Des. 9 (2009), 5327–5333; Croat. Chem. Acta. 84 (2011) 232-239; Crystengcomm. 13 (2011), 4314-4323; Chem. Eur. J. 18 (2012) 5620-5631.
2009 – Mentoring the student work (Zoran Kokan) awarded by the University of Zagreb Chancellor’s Award – later published as a Cryst. Growth Des. 9 (2009), 5327.
Featured Publications
51 publications in international peer-reviewed journals. 1276 citations, h index:20 (Google Scholar, 20/11/2019). An asterisk denotes the corresponding authorship. 1 preprint in ChemRxiv, also submitted for publication.
SELECTED PUBLICATIONS
● Bahar Karadeniz, Dijana Žilić, Igor Huskić, Luzia Germann, Athena M. Fidelli, Senada Mura-tović, Ivor Lončarić, Martin Etter, Robert. E. Dinnebier, Dajana Barišić, Nikola Cindro, Timur Islamoglu, Omar K. Farha, Tomislav Friščić, Krunoslav Užarević*, Controlling the polymorphism and topology transformation in porphyrinic zirconium metal-organic frameworks via mechanochemistry, J. Am. Chem. Soc. (2019), minor revision, (22.10.2019.)
● Ghada Ayoub, Bahar Karadeniz, Ashlee J. Howarth, Omar K. Farha, Ivica Đilović ,Luzia S. Germann, Robert E. Dinnebier, Krunoslav Užarević,* Tomislav Friščić*, Rational Synthesis of Mixed-Metal Microporous Metal-Organic Frameworks with Controlled Composition Using Mechanochemistry, Chemistry of Materials (2019), 31, 15, 5494-5501. DOI: 10.1021/acs.chemmater.9b01068.
● Nikola Cindro, Martina Tireli, Bahar Karadeniz, Tomislav Mrla, Krunoslav Užarević,* Investigations of Thermally Controlled Mechanochemical Milling Reactions, ACS Sustainable Chemistry & Engineering (2019) doi:10.1021/acssuschemeng.9b03319
● Krunoslav Užarević,* Nenad Ferdelji, Tomislav Mrla, Patrick A. Julien, Boris Halasz, Tomislav Friščić and Ivan Halasz, Enthalpy vs. friction: heat flow modeling of unexpected temperature profiles in mechanochemistry of metal-organic frameworks, Chemical Science, (2018), 9, 2525-2532; doi: 10.1039/C7SC05312F
● Stipe Lukin, Tomislav Stolar, Martina Tireli, Maria Blanco, Darko Babić, Tomislav Friščić, Krunoslav Užarević, Ivan Halasz, Tandem in situ monitoring for quantitative assessment of mechanochemical reactions involving structurally unknown phases, Chem. Eur. J. (2017), 23, 13941–13949; DOI: 10.1002/chem.201702489 (cover page)
● Patrick A. Julien, Krunoslav Užarević, Athanassios D Katsenis, Simon A. J. Kimber, Timothy C. Wang, Omar K. Farha, Yuancheng Zhang, Jose Casaban, Luzia Germann, Martin Etter, Robert E. Dinnebier, Stuart L. James, Ivan Halasz, Tomislav Friščić,In situ monitoring and mechanism of the mechanochemical formation of a microporous MOF-74 framework, J. Am. Chem. Soc.(2016), DOI: 10.1021/jacs.5b13038.
● Krunoslav Užarević, Timothy C. Wang, Su-Young Moon, Athena M. Fidelli, Joseph T. Hupp, Omar K. Farha, Tomislav Friščić, Mechanochemical and Solvent-free Assembly of Zirconium-Based Metal-organic Frameworks, Chem. Commun. (2016), 52, 2133-2136.
● K. Užarević, Ivan Halasz, Tomislav Friščić, Real-Time and In Situ Monitoring of Mechanochemical Reactions: A New Playground for All Chemists, J. Phys. Chem. Lett. (2015), 6, 4129–4140.
● A. D. Katsenis, V. Štrukil, C. Mottillo, P. A. Julien K. Užarević, M-H. Pham, T-O. Do, S. A. J. Kimber, P. Lazić, O. Magdyshyuk, R. E. Dinnebier, I. Halasz, T. Friščić, In situ X-ray diffraction monitoring of a mechanochemical reaction reveals a unique topology metal-organic framework, Nature Communications, (2015), 6, doi:10.1038/ncomms7662.
● D. Gracin, V. Štrukil, T. Friščić, I. Halasz, K. Užarević, Laboratory real-time and in situ monitoring of mechanochemical milling reactions using Raman spectroscopy, Angew. Chem. Int. Ed. (2014), 53, 6193-6197 (corresponding author).
● K. Užarević, I. Halasz, I. Đilović, N. Bregović, M. Rubčić, D. Matković-Čalogović and V. Tomišić, Dynamic molecular recognition in the solid state for separating mixtures of isomeric dicarboxylic acids, Angewandte Chemie International Edition (2013) 52, 5504-5508. (corresponding author)
● K. Užarević, M. Rubčić, M. Radić, A. Puškarić, and M. Cindrić, Mechanosensitive metal–ligand bonds in the design of new coordination compounds. CrystEngComm (2011), 13, 4314-4323. (corresponding author)
● K. Užarević, M. Rubčić, I. Ðilović, Z. Kokan, D. Matković-Čalogović, and M. Cindrić, Concomitant Conformational Polymorphism: Mechanochemical Reactivity and Phase Relationships in the (Methanol)cis-dioxo-(N-salicylidene-2-amino-3-hydroxypyridine) molybdenum(VI) Trimorph, Crystal Growth and Design (2009), 9, 5327–5333. (corresponding author)
● K. Užarević, I. Ðilović, D. Matković-Čalogović, D. Šišak, and M. Cindrić, Anion-Directed Self-Assembly of Flexible Ligands into Anion-Specific and Highly Symmetrical Organic Solids, Angewandte Chemie International Edition (2008) 47, 7022–7025.
Publications
Books and book chapters
Book chapters
Užarević, K., Stilinović, V. & Rubčić, M. (2016) Supramolecular Control over Tautomerism in Organic Solids. U: Antonov, L. (ur.) Tautomerism: Concepts and Applications in Science and Technology. Weinheim, Wiley-VCH Verlag GmbH & Co, str. 295-328.
Journal articles
Scientific and review papers
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Martinez, V., Stolar, T., Karadeniz, B., Brekalo, I. & Užarević, K. (2023) Advancing mechanochemical synthesis by combining milling with different energy sources. Nature Reviews Chemistry, 7, 51-65 doi:10.1038/s41570-022-00442-1.
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Alić, J., Stolar, T., Štefanić, Z., Užarević, K. & Šekutor, M. (2023) Sustainable synthesis of diamondoid ethers by high-temperature ball milling. ACS Sustainable Chemistry & Engineering, 11 (2), 617-624 doi:10.1021/acssuschemeng.2c05283.
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Thorne, M., Castillo-Blas, C., McHugh, L., Bumstead, A., Robertson, G., Sapnik, A., Coates, C., Sayed, F., Grey, C., Keen, D., Etter, M., da Silva, I., Užarević, K. & Bennett, T. (2022) Formation of new crystalline qtz-[Zn(mIm)2] polymorph from amorphous ZIF-8. Chemical communications, 58 (85), 11949-11952 doi:10.1039/d2cc04241j.
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Muratović, S., Martinez, V., Karadeniz, B., Pajić, D., Brekalo, I., Arhangelskis, M., Mazaj, M., Mali, G., Etter, M., Friščić, T., Krupskaya, Y., Kataev, V., Žilić, D. & Užarević, K. (2022) Low-Dimensional Magnetism in Multivariate Copper/Zinc MOF-74 Materials Formed via Different Mechanochemical Methods. Inorganic chemistry, 61 (45), 18181-18192 doi:10.1021/acs.inorgchem.2c02898.
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McHugh, L., Thorne, M., Chester, A., Etter, M., Užarević, K. & Bennett, T. (2022) Mechanochemically synthesised dicyanamide hybrid organic–inorganic perovskites, and their melt-quenched glasses. Chemical communications, 58 (24), 3949-3952 doi:10.1039/d2cc00278g.
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Stolar, T., Alić, J., Lončarić, I., Etter, M., Jung, D., Farha, K., Đilović, I., Meštrović, E. & Užarević, K. (2022) Sustainable solid form screening: mechanochemical control over nucleobase hydrogen-bonded organic framework polymorphism. Crystengcomm, 24, 6505-6511 doi:10.1039/D2CE00668E.
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Brekalo, I., Martinez, V., Karadeniz, B., Orešković, P., Drapanauskaite, D., Vriesema, H., Stenekes, R., Etter, M., Dejanović, I., Baltrusaitis, J. & Užarević, K. (2022) Scale-up of agrochemical urea-gypsum cocrystal synthesis using thermally controlled mechanochemistry. ACS Sustainable Chemistry & Engineering, 10 (20), 6743-6754 doi:10.1021/acssuschemeng.2c00914.
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Barišić, D., Lešić, F., Tireli Vlašić, M., Užarević, K., Bregović, N. & Tomišić, V. (2022) Anion binding by receptors containing NH donating groups - What do anions prefer?. Tetrahedron, 120, 132875, 8 doi:10.1016/j.tet.2022.132875.
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Puccetti, F., Lukin, S., Užarević, K., Colacino, E., Halasz, I., Bolm, C. & Hernández, J. (2022) Mechanistic Insights on the Mechanosynthesis of Phenytoin, a WHO Essential Medicine. Chemistry : a European journal, 28 (13), e202104409, 5 doi:10.1002/chem.202104409.
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Stolar, T., Grubešić, S., Cindro, N., Meštrović, E., Užarević, K. & Hernández, J. (2021) Mechanochemical Prebiotic Peptide Bond Formation. Angewandte Chemie. International edition, 60 (23), 12727-12731 doi:10.1002/anie.202100806.
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Lukin, S., Užarević, K. & Halasz, I. (2021) Raman spectroscopy for real-time and in situ monitoring of mechanochemical milling reactions. Nature Protocols, 16, 3492-3521 doi:10.1038/s41596-021-00545-x.
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Catalano, L., Germann, L., Julien, P., Arhangelskis, M., Halasz, I., Užarević, K., Etter, M., Dinnebier, R., Ursini, M., Cametti, M., Martí-Rujas, J., Friščić, T., Metrangolo, P., Resnati, G. & Terraneo, G. (2021) Open versus Interpenetrated: Switchable Supramolecular Trajectories in Mechanosynthesis of a Halogen-Bonded Borromean Network. Chem, 7 (1), 146-154 doi:10.1016/j.chempr.2020.10.022.
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Stolar, T., Prašnikar, A., Martinez, V., Karadeniz, B., Bjelić, A., Mali, G., Friščić, T., Likozar, B. & Užarević, K. (2021) Scalable Mechanochemical Amorphization of Bimetallic Cu−Zn MOF-74 Catalyst for Selective CO2 Reduction Reaction to Methanol. ACS applied materials & interfaces, 13 (2), 3070-3077 doi:10.1021/acsami.0c21265.
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Milanović, I., Biliškov, N., Užarević, K., Lukin, S., Etter, M. & Halasz, I. (2021) Mechanochemical Synthesis and Thermal Dehydrogenation of Novel Calcium-Containing Bimetallic Amidoboranes. ACS Sustainable Chemistry & Engineering, 9 (5), 2089-2099 doi:10.1021/acssuschemeng.0c06839.
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Germann, L., Katsenis, A., Huskić, I., Julien, P., Užarević, K., Etter, M., Farha, O., Friščić, T. & Dinnebier, R. (2020) Real-Time in Situ Monitoring of Particle and Structure Evolution in the Mechanochemical Synthesis of UiO-66 Metal–Organic Frameworks. Crystal growth & design, 20 (1), 49-54 doi:10.1021/acs.cgd.9b01477.
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Martinez, V., Karadeniz, B., Biliškov, N., Lončarić, I., Muratović, S., Žilić, D., Avdoshenko, S., Roslova, M., Popov, A. & Užarević, K. (2020) Tunable Fulleretic Sodalite MOFs: Highly Efficient and Controllable Entrapment of C60 Fullerene via Mechanochemistry. Chemistry of Materials, 32 (24), 10628-10640 doi:10.1021/acs.chemmater.0c03796.
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Stolar, T., Lukin, S., Etter, M., Rajić Linarić, M., Užarević, K., Meštrović, E. & Halasz, I. (2020) DNA-specific selectivity in pairing of model nucleobases in the solid state. Chemical communications, 56, 13524-13527 doi:10.1039/d0cc03491f.
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Muratović, S., Karadeniz, B., Stolar, T., Lukin, S., Halasz, I., Herak, M., Mali, G., Krupskaya, Y., Kataev, V., Žilić, D. & Užarević, K. (2020) Impact of dehydration and mechanical amorphization on the magnetic properties of Ni(ii)-MOF-74. Journal of Materials Chemistry C, 8, 7132-7142 doi:10.1039/D0TC00844C.
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Smokrović, K., Muratović, S., Karadeniz, B., Užarević, K., Žilić, D. & Đilović, I. (2020) Synthon Robustness and Structural Modularity of Copper(II) Two-Dimensional Coordination Polymers with Isomeric Amino Acids and 4,4′-Bipyridine. Crystal growth & design, 20 (4), 2415-2423 doi:10.1021/acs.cgd.9b01601.
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Stolar, T. & Užarević, K. (2020) Mechanochemistry: an efficient and versatile toolbox for synthesis, transformation, and functionalization of porous metal–organic frameworks. Crystengcomm, 22 (27), 4511-4525 doi:10.1039/d0ce00091d.
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Ardila-Fierro, K., Lukin, S., Etter, M., Užarević, K., Halasz, I., Bolm, C. & Hernández, J. (2020) Direct visualization of a mechanochemically induced molecular rearrangement. Angewandte Chemie. International edition, 59 (32), 13458-13462 doi:10.1002/anie.201914921.
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Karadeniz, B., Žilić, D., Huskić, I., Germann, L., Fidelli, A., Muratović, S., Lončarić, I., Etter, M., Dinnebier, R., Barišić, D., Cindro, N., Islamoglu, T., Farha, O., Friščić, T. & Užarević, K. (2019) Controlling the Polymorphism and Topology Transformation in Porphyrinic Zirconium Metal– Organic Frameworks via Mechanochemistry. Journal of the American Chemical Society, 141 (49), 19214-19120 doi:10.1021/jacs.9b10251.
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Cindro, N., Tireli, M., Karadeniz, B., Mrla, T. & Užarević, K. (2019) Investigations of Thermally Controlled Mechanochemical Milling Reactions. ACS Sustainable Chemistry & Engineering, 7 (19), 16301-16309 doi:10.1021/acssuschemeng.9b03319.
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Ayoub, G., Karadeniz, B., Howarth, A., Farha, O., Đilović, I., Germann, L., Dinnebier, R., Užarević, K. & Friščić, T. (2019) Rational Synthesis of Mixed-Metal Microporous Metal–Organic Frameworks with Controlled Composition Using Mechanochemistry. Chemistry of materials, 31 (15), 5494-5501 doi:10.1021/acs.chemmater.9b01068.
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Stolar, T., Lukin, S., Tireli, M., Sović, I., Karadeniz, B., Kereković, I., Matijašić, G., Gretić, M., Katančić, Z., Dejanović, I., Michiel, M., Halasz, I. & Užarević, K. (2019) Control of pharmaceutical cocrystal polymorphism on various scales by mechanochemistry: transfer from the laboratory batch to the large-scale extrusion processing. ACS Sustainable Chemistry & Engineering, 7 (7), 7102-7110 doi:10.1021/acssuschemeng.9b00043.
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You, J., Carić, D., Rakvin, B., Štefanić, Z., Užarević, K. & Kveder, M. (2019) Matrix material structure dependence of the embedded electron spin decoherence. The Journal of chemical physics, 150 (16), 164124, 9 doi:10.1063/1.5090215.
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Lukin, S., Tireli, M., Stolar, T., Barišić, D., Blanco, M., di Michiel, M., Užarević, K. & Halasz, I. (2019) Isotope Labeling Reveals Fast Atomic and Molecular Exchange in Mechanochemical Milling Reactions. Journal of the American Chemical Society, 141 (3), 1212-1216 doi:10.1021/jacs.8b12149.
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Barišić, D., Cindro, N., Juribašić Kulcsár, M., Tireli, M., Užarević, K., Bregović, N. & Tomišić, V. (2019) Protonation and anion binding properties of aromatic bis‐urea derivatives – apprehending the proton transfer. Chemistry : a European journal, 25 (18), 4695-4706 doi:10.1002/chem.201805633.
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Lukin, S., Tireli, M., Lončarić, I., Barišić, D., Šket, P., Vrsaljko, D., di Michiel, M., Plavec, J., Užarević, K. & Halasz, I. (2018) Mechanochemical carbon-carbon bond formation that proceeds via a cocrystal intermediate. Chemical communications, 54, 13216-13219 doi:10.1039/C8CC07853J.
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Karadeniz, B., Howarth, A., Stolar, T., Islamoglu, T., Dejanović, I., Tireli, M., Wasson, M., Moon, S., Farha, O., Friščić, T. & Užarević, K. (2018) Benign by design: Green and scalable synthesis of zirconium UiO-metal−organic frameworks by water-assisted mechanochemistry. ACS Sustainable Chemistry & Engineering, 6 (11), 15841-15849 doi:10.1021/acssuschemeng.8b04458.
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Bjelopetrović, A., Lukin, S., Halasz, I., Užarević, K., Đilović, I., Barišić, D., Budimir, A., Juribašić Kulcsar, M. & Ćurić, M. (2018) Mechanism of Mechanochemical C–H Bond Activation in an Azobenzene Substrate by Pd(II) Catalysts. Chemistry : a European journal, 24 (42), 10672-10682 doi:10.1002/chem.201802403.
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Fidelli, A., Karadeniz, B., Howarth, A., Huskić, I., Germann, L., Halasz, I., Etter, M., Moon, S., Dinnebier, R., Stilinović, V., Farha, O., Friščić, T. & Užarević, K. (2018) Green and rapid mechanosynthesis of high-porosity NU- and UiO-type metal–organic frameworks. Chemical communications, 54 (51), 6999-7002 doi:10.1039/c8cc03189d.
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Lukin, S., Lončarić, I., Tireli, M., Stolar, T., Blanco, M., Lazić, P., Užarević, K. & Halasz, I. (2018) Experimental and Theoretical Study of Selectivity in Mechanochemical Cocrystallization of Nicotinamide with Anthranilic and Salicylic Acid. Crystal growth & design, 18 (3), 1539-1547 doi:10.1021/acs.cgd.7b01512.
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Užarević, K., Ferdelji, N., Mrla, T., Julien, P., Halasz, B., Friščić, T. & Halasz, I. (2018) Enthalpy vs. friction: heat flow modelling of unexpected temperature profiles in mechanochemistry of metal–organic frameworks. Chemical Science, 9, 2525-2532 doi:10.1039/c7sc05312f.
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Lukin, S., Stolar Tomislav, Tireli, M., Barišić, D., Di Michiel, M., Užarević, K. & Halasz, I. (2017) Solid-State Supramolecular Assembly of Salicylic Acid and 2-Pyridone, 3-Hydroxypyridine or 4-Pyridone. Croatica chemica acta, 90 (4), 707-710 doi:10.5562/cca3339.
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Biliškov, N., Borgschulte, A., Užarević, K., Halasz, I., Lukin, S., Milošević, S., Milanović, I. & Grbović Novaković, J. (2017) In-situ and Real-time Monitoring of Mechanochemical Preparation of Li2Mg(NH2BH3)4 and Na2Mg(NH2BH3)4 and their Thermal Dehydrogenation. Chemistry : a European journal, 23, 16274-16282 doi:10.1002/chem.201702665.
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Tireli, M., Maračić, S., Lukin, S., Juribašić Kulcsar, M., Žilić, D., Cetina, M., Halasz, I., Raić-Malić, S. & Užarević, K. (2017) Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole. Beilstein journal of organic chemistry, 13, 2352-2363 doi:10.3762/bjoc.13.232.
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Stolar, T., Batzdorf, L., Lukin, S., Žilić, D., Motillo, C., Friščić, T., Emmerling, F., Halasz, I. & Užarević, K. (2017) In Situ Monitoring of the Mechanosynthesis of the Archetypal Metal–Organic Framework HKUST-1 : Effect of Liquid Additives on the Milling Reactivity. Inorganic chemistry, 56 (11), 6599-6608 doi:10.1021/acs.inorgchem.7b00707.
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Lukin, S., Stolar, T., Tireli, M., Blanco, M., Babić, D., Friščić, T., Užarević, K. & Halasz, I. (2017) Tandem in situ monitoring for quantitative assessment of mechanochemical reactions involving structurally unknown phases. Chemistry : a European journal, 23, 13941-13949 doi:10.1002/chem.201702489.
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Bregović, N., Cindro, N., Bertoša, B., Barišić, D., Frkanec, L., Užarević, K. & Tomišić, V. (2017) Dehydroacetic acid derivatives bearing amide and urea moieties as effective anion receptors. Chemistry : a European journal, 23 (43), 10396-10406 doi:10.1002/chem.201701677.
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Juribašić Kulcsar, M., Halasz, I., Budimir, A., Užarević, K., Lukin, S., Monas, A., Emmerling, F., Plavec, J. & Ćurić, M. (2017) Reversible Gas−Solid Ammonia N−H Bond Activation Mediated by an Organopalladium Complex. Inorganic chemistry, 56 (9), 5342-5351 doi:10.1021/acs.inorgchem.7b00422.
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Monas, A., Užarević, K., Halasz, I., Juribašić Kulcsar, M. & Ćurić, M. (2016) Vapour-induced solid-state C–H bond activation for the clean synthesis of an organopalladium biothiol sensor. Chemical communications, 52 (88), 12960-12963 doi:10.1039/c6cc06062e.
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Stolar, T., Lukin, S., Požar, J., Rubčić, M., Day, G., Biljan, I., Šišak Jung, D., Horvat, G., Užarević, K., Meštrović, E. & Halasz, I. (2016) Solid-State Chemistry and Polymorphism of the Nucleobase Adenine. Crystal growth & design, 16 (6), 3262-3270 doi:10.1021/acs.cgd.6b00243.
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Huskić, I., Christopherson, J., Užarević, K. & Friščić, T. (2016) In situ monitoring of vapour-induced assembly of pharmaceutical cocrystals using a benchtop powder X-ray diffractometer. Chemical communications, 52, 5120-5123 doi:10.1039/C6CC01583B.
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Užarević, K., Štrukil, V., Mottillo, C., Julien, P., Puškarić, A., Friščić, T. & Halasz, I. (2016) Exploring the effect of temperature on a mechanochemical reaction by in situ synchrotron powder X-ray diffraction. Crystal growth & design, 16 (4), 2342-2347 doi:10.1021/acs.cgd.6b00137.
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Julien, P., Užarević, K., Katsenis, A., Kimber, S., Wang, T., Farha, O., Zhang, Y., Casaban, J., Germann, L., Etter, M., Dinnebier, R., James, S., Halasz, I. & Friščić, T. (2016) In situ monitoring and mechanism of the mechanochemical formation of a microporous MOF-74 framework. Journal of the American Chemical Society, 138 (9), 2929-2932 doi:10.1021/jacs.5b13038.
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Užarević, K., Wang, T., Moon, S., Fidelli, A., Hupp, J., Farha, O. & Friščić, T. (2016) Mechanochemical and Solvent-free Assembly of Zirconium-Based Metal-organic Frameworks. Chemical communications, 52, 2133-2136 doi:10.1039/c5cc08972g.
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Užarević, K., Halasz, I. & Friščić, T. (2015) Real-Time and In Situ Monitoring of Mechanochemical Reactions : A New Playground for All Chemists. Journal of physical chemistry letters, 6 (20), 4129-4140 doi:10.1021/acs.jpclett.5b01837.
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Katsenis, A., Puškarić, A., Štrukil, V., Mottillo, C., Julien, P., Užarević, K., Pham, M., Do, T., Kimber, S., Lazić, P., Magdysyuk, O., Dinnebier, R., Halasz, I. & Friščić, T. (2015) In situ X-ray diffraction monitoring of a mechanochemical reaction reveals a unique topology metal-organic framework. Nature Communications, 6, 6662-1 doi:10.1038/ncomms7662.
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Tireli, M., Juribašić Kulcsar, M., Cindro, N., Gracin, D., Biliškov, N., Borovina, M., Ćurić, M., Halasz, I. & Užarević, K. (2015) Mechanochemical reactions studied by in situ Raman spectroscopy : base catalysis in liquid-assisted grinding. Chemical communications, 51 (38), 8058-8061 doi:10.1039/c5cc01915j.
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Đilović, I. & Užarević Krunoslav (2015) Conformational adaptations of acyclic receptor templated by weakly coordinating anions. Crystengcomm, 17, 3153-3161 doi:10.1039/C4CE02413C.
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Bregović, N., Cindro, N., Frkanec, L., Užarević, K. & Tomišić, V. (2014) Thermodynamic study of dihydrogen phosphate dimerisation and complexation with novel urea- and thiourea-based receptors. Chemistry : a European journal, 20 (48), 15863-15871 doi:10.1002/chem.201404091.
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Juribašić, M., Užarević, K., Gracin, D. & Ćurić, M. (2014) Mechanochemical C–H bond activation : rapid and regioselective double cyclopalladation monitored by in situ Raman Spectroscopy. Chemical communications, 50 (71), 10287-10290 doi:0.1039/C4CC04423A.
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Juribašić, M., Bregović, N., Stilinović, V., Tomišić, V., Cindrić, M., Šket, P., Plavec, J., Rubčić, M. & Užarević, K. (2014) Supramolecular stabilization of metastable tautomers in solution and solid state. Chemistry : a European journal, 20 (52), 17333-17345 doi:10.1002/chem.201403543.
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Gracin, D., Štrukil, V., Friščić, T., Halasz, I. & Užarević, K. (2014) Laboratory real-time and in situ monitoring of mechanochemical milling reactions using Raman spectroscopy. Angewandte Chemie. International edition, 53 (24), 6193-6197 doi:10.1002/anie.201402334.
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Halasz, I., Friščić, T., Kimber, S., Užarević, K., Puškarić, A., Mottillo, C., Julien, P., Štrukil, V., Honkimäki, V. & Dinnebier, R. (2014) Quantitative in situ and real-time monitoring of mechanochemical reactions. Faraday discussions, 170, 203-221 doi:10.1039/C4FD00013G.
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Užarević, K., Halasz, I., Đilović, I., Bregović, N., Rubčić, M., Matković-Čalogović, D. & Tomišić, V. (2013) Dynamic Molecular Recognition in Solid State for Separating Mixtures of Isomeric Dicarboxylic Acids. Angewandte Chemie. International edition, 52 (21), 5504-5508 doi:10.1002/anie.201301032.
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Užarević, K., Kokan, Z., Perić, B., Bregović, N. & Kirin, S. (2013) Concomitant polymorphism in the pseudo-peptide Me2N-pC6H4C(O)-Phe-OEt. Journal of molecular structure, 1031, 160-167 doi:10.1016/j.molstruc.2012.07.026.
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Schilf, W., Kamieński, B. & Užarević, K. (2013) Nitrogen and carbon CPMAS NMR investigations of keto-enol tautomerism in asymmetric o-hydroxy Schiff bases. Journal of molecular structure, 1013, 211-215 doi:10.1016/j.molstruc.2012.10.004.
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Užarević, K., Pavlović, G. & Cindrić, M. (2013) Mononuclear and polynuclear molybdenum(VI) complexes with the interchangeable coordination site. Polyhedron, 52, 294-300 doi:10.1016/j.poly.2012.09.023.
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Stilinović, V., Užarević, K., Cvrtila, I. & Kaitner, B. (2012) Bis(morpholine) hydrogen bond pincer – a novel series of heteroleptic Cu(II) coordination compounds as receptors for electron rich guests. Crystengcomm, 14 (21), 7493-7501 doi:10.1039/c2ce25848j.
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Rubčić, M., Užarević, K., Halasz, I., Bregović, N., Mališ, M., Đilović, I., Kokan, Z., Stein, R., Dinnebier, R. & Tomišić, V. (2012) Desmotropy, Polymorphism, and Solid-State Proton Transfer : Four Solid Forms of an Aromatic o-Hydroxy Schiff Base. Chemistry : a European journal, 18 (18), 5620-5631 doi:10.1002/chem.201103508.
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Užarević, K., Đilović, I., Bregović, N., Tomišić, V., Matković-Čalogović, D. & Cindrić, M. (2011) Anion-Templated Supramolecular C3-Assembly for Efficient Inclusion of Charge-Dispersed Anions into Hydrogen-Bonded Networks. Chemistry : a European journal, 17 (39), 10889-10897 doi:10.1002/chem.201101127.
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Užarević, K., Rubčić, M., Radić, M., Puškarić, A. & Cindrić, M. (2011) Mechanosensitive metal–ligand bonds in the design of new coordination compounds. Crystengcomm, 13 (13), 4314-4323 doi:10.1039/c0ce00807a.
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Jednačak, T., Novak, P., Užarević, K., Bratoš, I., Marković, J. & Cindrić, M. (2011) Bioactive Phenylenediamine Derivatives of Dehydroacetic Acid : Synthesis, Structural Characterization and Deuterium Isotope Effects. Croatica chemica acta, 84 (2), 203-209 doi:10.5562/cca1825.
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Halasz, I., Rubčić, M., Užarević, K., Đilović, I. & Meštrović, E. (2011) The cocrystal of 4-oxopimelic acid and 4, 4′-bipyridine: polymorphism and solid-state transformations. New journal of chemistry, 35 (1), 24-27 doi:10.1039/c0nj00569j.
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Užarević, K., Rubčić, M., Stilinović, V., Kaitner, B. & Cindrić, M. (2010) Keto–enol tautomerism in asymmetric Schiff bases derived from p-phenylenediamine. Journal of molecular structure, 984 (1/3), 232-239 doi:10.1016/j.molstruc.2010.09.034.
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Užarević, K., Rubčić, M., Đilović, I., Kokan, Z., Matković-Čalogović, D. & Cindrić, M. (2009) Concomitant Conformational Polymorphism: Mechanochemical Reactivity and Phase Relationships in the (Methanol)cis-dioxo(N-salicylidene-2-amino-3-hydroxypyridine)molybdenum(VI) Trimorph. Crystal Growth and Design, 9 (12), 5327-5333 doi:10.1021/cg900824n.
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Užarević, K., Đilović, I., Matković-Čalogović, D., Šišak, D. & Cindrić, M. (2008) Anion-directed self-assembly of flexible ligands into anion-specific and highly symmetrical organic solids. Angewandte Chemie. International edition, 47 (37), 7022-7025 doi:10.1002/anie.200802193.
doi Oreščanin, V., Mikelić, L., Sofilić, T., Rastovčan-Mioč, A., Užarević, K., Medunić, G., Elez, L. & Lulić, S. (2007) Leaching Properties of Electric Arc Furnace Dust Prior/Following Alkaline Extraction. Journal of Environmental Science & Health. Part A, 42 (3), 323-329. (https://www.bib.irb.hr/253373).
Cindrić, M., Kajfež Novak, T. & Užarević, K. (2005) Molecular and crystal structures of N, N'-propylene- and N, N'- phenylene-diylbis[3-(1-aminoethyl)-6-methyl-2H-pyran-2, 4(3H)-dione]. Journal of molecular structure, 750, 135-141.
Membership in professional associations / societies
Croatian Chemical Society
Croatian Crystallographic Association
Canadian Institute of Chemistry
Reviewer for ACS Applied Materials and Interfaces, Chemical Communications, ACS Sustainable Chemistry and Engineering, Nanoscale, Crystal Growth & Design, CrystEngComm, ChemistrySelect, Chemistry-An Asian Journal, RSC Advances, Dalton Transactions, New Journal of Chemistry, Journal of Molecular Structure, Croatica Chemica Acta, Vibrational Spectroscopy, Contributions, Small Methods, Kemija u industriji.
Scientific interests and motivation
My general scientific interests are in the solid-state chemistry of supramolecular host-guest complexes and in the field of coordination compounds, with special emphasis on microporous metal-organic frameworks. In my research, I combine and compare solution- and solvent-free approaches for synthesis and manipulation of target compounds. These solid-state approaches include mechanochemistry, thermal methods and gas-solid reactions.
In situ methods for monitoring of mechanochemical and vapour-induced solid-state rections
Development of instrumentation and methodology for the in situ monitoring of mechanochemical reactions is performed in collaboration with Friščić Research Group from McGill University, Montreal. It was motivated by almost complete lack of knowledge about the mechanisms of milling reactions, despite their popularity in the materials chemistry and green synthesis. Our recently developed methods for in situ monitoring by synchrotron X-ray diffraction (Nature Chem, (2013), 5, 66; J. Phys. Chem. Lett. (2015), 6, 4129) and by Raman spectroscopy (Angew. Chem. Int. Ed. (2014), 53, 6193) offered unique insight into mechanochemical milling reactivity. They revealed complex behaviour of mechanochemical solid-state reactions, which often proceed in stepwise manner involving different intermediates and provided means for evaluating the role of additives on milling reactions.
Flexible anion receptors
Major part of my research in the field deals with flexible anion receptors, i.e. molecules that employ specific binding functionalities to recognise and selectively bind target specie. During the recognition process, such receptors can change their conformation to adapt to the specific requirements of the guest, and they rarely display high peak selectivity in solution. However, in such systems selectivity is often achieved by selective crystallisation. In our studies, we have developed highly adaptable[1,2] and at the same time highly selective receptor for environmentally important nitrate and sulfate anions. By crystallisation of receptor-anion complexes to hydrogen-bonded networks, these anions were separated form solutions containing large excess of competing anions.
Selective grinding
In our latest study[3] we proved that flexible polyamine receptor is capable to recognise and selectively bind isomeric organic guests from their solid mixtures during the milling process. Regardless of whether the recognition takes place in the solid state via milling or by crystallisation from solution, the resulting supramolecular complexes are the same and the selectivity bias of the receptor towards the guest acids is fully retained. Milling improved yields to quantitative and almost eliminated the use of solvent.
Mechanosensitive metal-ligand bonds in the synthesis of new coordination compounds
In the design of discrete and extended coordination systems, synthesis from preorganized homoleptic or heteroleptic coordination compounds is often utilised. Although each of the types is valuable under specific synthetic requirements, heteroleptic complexes tend to be more advantageous when only a certain amount and type of ligands need to be replaced (ancillary).[4] Such an approach also allows a high level of control over the resulting structure because substitution takes place only at strictly defined coordination sites. We employed various solvent-free approaches (mechanochemistry, thermal methods) to selectively remove specific ligand from the central metal coordination sphere, resulting in coordinatively unsaturated compound. Coordinatively unsaturated complexes, due to their higher reactivity, can be considered as “activated” species and as such are better precursors since there is no competition (discrimination) between the departing and the incoming ligand.[4] In our studies we compare solution and solvent-free synthetic approaches which prove to be superior under specific conditions and their respective advantages and weaknesses are object of examination.[5] While our recent studies included complexes with one mechanosensitive bond, we are concentrated on the study of precursors with two or more mechanosensitive sites and they potential application in the controllable synthesis of higher-ordered coordination networks.
Solid-State Tautomerism
Specific class of ligands used in our laboratory for synthesis of coordination compounds are characterised by strong intramolecular N…H…O hydrogen bond and can occur in the solid state as keto-amino or enol-imino tautomers. Proton transfer in such compounds is usually related with their reactivity, but also with macroscopic properties such as thermochromism and photochromism. Although such compounds and accompanying phenomena have been widely studied, the mechanism of this apparently simple solid-state rearrangement still presents a number of challenges. Main reason for this is that, in contrast to solution, where different tautomers coexist, in the solid state usually only one tautomer appears. Our studies included synthesis of the compounds comprising keto-amino and enol-imino subunits[6] and a unique example of a Schiff base which have crystallised separately as a two polymorphic pairs of keto-amino and enol-imino tautomers, i.e. desmotrops.[7] The relative stabilities and interconversions of the four phases were assessed via various solution and solid-state methods and evaluated against the results of a computational study. Our findings emphasize the importance of intermolecular forces in stabilization of the less stable keto tautomer in the solid state.
References
[1] K. Užarević, I. Ðilović, D. Matković-Čalogović, D. Šišak, and M. Cindrić, Angew. Chem. Int. Ed. (2008) 47, 7022–7025.
[2] K. Užarević, I. Ðilović, N. Bregović, V. Tomišić, D. Matković-Čalogović, and M. Cindrić, Chem. Eur. J. (2011), 17, 10889-10897. (corresponding author)
[3] K. Užarević, I. Halasz, I. Đilović, N. Bregović, M. Rubčić, D. Matković-Čalogović and V. Tomišić, Angew. Chem. Int. Ed. (2013) prihvaćen za objavljivanje, doi: 10.1002/anie.201301032. (corresponding author)
[4] K. Užarević, M. Rubčić, I. Ðilović, Z. Kokan, D. Matković-Čalogović, and M. Cindrić, Cryst. Growth Des. (2009), 9,5327–5333. (corresponding author).
[5] K. Užarević, M. Rubčić, M. Radić, A. Puškarić, and M. Cindrić, CrystEngComm (2011), 13, 4314-4323. (corresponding author)
[6] K. Užarević, M. Rubčić, V. Stilinović, B. Kaitner and M. Cindrić, J. Mol. Struct. 984 (2010), 232-239. (corresponding author)
[7] M. Rubčić, K. Užarević, I. Halasz, N. Bregović, M. Mališ, I. Đilović, Z. Kokan, R. S. Stein, R. E. Dinnebier and V. Tomišić, Chem. Eur. J. (2012) 18, 5620–5631. (corresponding author)