Laboratory for Green Synthesis

Laboratory for Green Synthesis

Laboratory for Green Synthesis is dedicated to developing mechanochemical and solvent-free procedures for the synthesis of various classes of functional materials, from supramolecular receptors and organic compounds, to microporous metal-organic frameworks (MOFs) and organometallic catalysts or chromogenic sensors.

Furthermore, we are focused on developing new methodologies for in situ monitoring of milling and aging reactions by synchrotron X-ray diffraction, Raman spectroscopy and thermal methods. We have active collaborations with scientific groups from around the world (McGill University, Max Planck Institute for Solid State Research, Stuttgart, ESRF Grenoble, BAM Berlin, DESY Hamburg).

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Laboratory for Green Synthesis (LGS) was founded in 2016 as a part of Division of Physical Chemistry. The scientific focus of the LGS is mostly in developing new, solvent-free procedures for synthesis and transformations of different functional materials, from pharmaceutical cocrystals and metal-organic frameworks to pure inorganic materials and nanoparticles. Furthermore, we are interested in phenomena related to mechanochemistry, accelerated aging and in the manipulation of solids by thermal methods.

At this moment, LGS has three projects from Croatian Science Foundation, one project of Adris foundation and ongoing collaboration with pharmaceutical industry.

Important part of our studies is development of instrumentation and software for direct and in situ methods for monitoring of mechanochemical and aging reactions. For his contribution in the field, Dr Ivan Halasz was awarded with The Annual State Award for Science in 2015.

Alen Bjelopetrović

+385 1 456 1158
1358

Dajana Barišić

+385 1 456 1158
1358

Ivan Halasz
PhD

research associate
+385 1 457 1217
1295

Krunoslav Užarević
dr. sc.

Higher Research Associate
Head of Laboratory for Green Synthesis
+385 1 457 1217
1295 1432
+385959164238

Manda Ćurić
PhD

Senior Research Associate
+385 1 468 0097
1295 1432

Marina Juribašić Kulcsar
Dr

research associate
+385 1 457 1217
1295 1432

Martina Tireli
mag. appl. chem.

Research Assistant
1207 1820

Ovaj popis predstavlja isključivo radove povezane s tematikom Laboratorija, a na kojima su članovi Laboratorija za zelenu sintezu nositelji tematike i glavni autori. Za ukupnu listu radova molimo pogledati u bibliografiju članova Laboratorija.

2017

31. 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), 56, 13941–13949, DOI: 10.1002/chem.201702489. (COVER PAPER)

30. Nikola Biliškov, Andreas Borgschulte, Krunoslav Užarević, Ivan Halasz, Stipe Lukin, Sanja Milošević, Igor Milanović, Jasmina Grbović Novaković, In-Situ and Real-time Monitoring of Mechanochemical Preparation of Li2Mg(NH2BH3)4 and Na2Mg(NH2BH3)4 and Their Thermal Dehydrogenation, Chem. Eur. J. (2017), 23, accepted, DOI: 10.1002/chem.201702665

29. Martina Tireli, Silvija Maračić, Stipe Lukin, Marina Juribašić Kulcsar, Dijana Žilić, Mario Cetina, Ivan Halasz, Silvana Raić-Malić, Krunoslav Užarević, Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinolone and 1,2,3-triazole, Beil. J. Org. Chem. (2017), 13, 2352–2363. doi:10.3762/bjoc.13.232 

28. Tomislav Stolar, Lisa Batzdorf, Stipe Lukin, Dijana Žilić, Cristina Motillo, Tomislav Friščić, Franziska Emmerling, Ivan Halasz, Krunoslav Užarević, In situ monitoring of mechanosynthesis of the archetypal metal-organic framework HKUST-1: the effect of liquid additives on milling reactivity, Inorg. Chem., (2017), 56,  6599–6608; DOI: 10.1021/acs.inorgchem.7b00707

27. M. Juribašić Kulcsár, I. Halasz, A. Budimir, K. Užarević, S. Lukin, F. Emmerling, J. Plavec, M. Ćurić, Reversible Gas-Solid Ammonia N–H Bond Activation Mediated by an Organopalladium Complex, Inorg. Chem., (2017), 56, 5342–5351.

2016

26. A. Hadžiev, K. Užarević, I. Halasz, M. Juribašić Kulcsár, M. Ćurić, Vapour-induced solid-state C–H bond activation for the clean synthesis of an organopalladium biothiol sensor, Chem. Commun. (2016), 52, 12960-12963. DOI: 10.1039/C6CC06062E.

25. T. Stolar, S. Lukin, J. Požar, M. Rubčić, G. M. Day, I. Biljan, D. Šišak Jung, G. Horvat, K. Užarević, E. Meštrović, I. Halasz, Solid-State Chemistry and Polymorphism of the Nucleobase Adenine. Cryst. Growth Des. (2016), 16, 3262-3270. DOI: 10.1021/acs.cgd.6b00243.

24. Krunoslav Užarević, Vladimir Stilinović, Mirta Rubčić, Supramolecular Control over Tautomerism in Organic Solids // Tautomerism: Concepts and Applications in Science and Technology / Antonov, Liudmil (ur.). Weinheim, Germany : Wiley-VCH Verlag GmbH & Co, 2016. pp 295-328. (Book chapter)

23. Krunoslav Užarević, Vjekoslav Štrukil, Cristina Mottillo, Patrick A. Julien, Andreas Puškarić, Tomislav Friščić, Ivan Halasz, Exploring the Effect of Temperature on a Mechanochemical Reaction by in Situ Synchrotron Powder X-ray DiffractionCrystal Growth Design (2016), 16, 2342-2347. DOI: 10.1021/acs.cgd.6b00137.

22. I. Huskić, Jan-Constantin Christopherson, K. Užarević, T. Friščić, In situ monitoring of vapour-induced assembly of pharmaceutical cocrystals using a benchtop powder X-ray diffractometerChem. Commun.(2016), 52, pp 5120-5123; DOI: 10.1039/C6CC01583B.

21. 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), 138, pp 2929–2932, DOI: 10.1021/jacs.5b13038.

20. 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 FrameworksChem. Commun. (2016), 52, pp 2133-2136.

2015

19. K. Užarević, I. Halasz, T. Friščić, Real-Time and In Situ Monitoring of Mechanochemical Reactions: A New Playground for All ChemistsJ. Phys. Chem. Lett.(2015), 6, pp 4129–4140.

18. M. Tireli, M. Juribašić Kulcsár, N. Cindro, M. Borovina, D. Gracin, M. Ćurić, I. Halasz, K.Užarević, Mechanochemical reactions studied by in situ Raman spectroscopy: base catalysis in liquid-assisted grindingChemical Communications (2015) 51, pp 8058-8061.

17. 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 frameworkNature Communications, (2015), 6, doi:10.1038/ncomms7662.

16. I. Đilović,K. Užarević, Conformational adaptations of acyclic receptor templated by weakly coordinating anions; CrystEngComm, (2015), 17, pp 3153-3161.

2014

15. I. Halasz, T. Friščić, S. A. Kimber, K. Užarević, A. Puškarić, C. Motillo, P. Julien, V. Štrukil, V. Honkimäki, R. E. Dinnebier, Quantitative in situ and real time monitoring of mechanochemical reactionsFaraday Discussions, (2014), 170, 203-221

14. M. Juribašić, N. Bregović, V. Stilinović, V. Tomišić, M. Cindrić, P. Šket, J. Plavec, M. Rubčić,K. Užarević, Supramolecular stabilization of metastable tautomers in solution and solid state Chem. Eur. J. (2014) 20, 17333-17345,

Hot article; Article highlighted on the inner cover of the issue.

13. M. Juribašić, K. Užarević, D. Gracin, M. Ćurić, Mechanochemical C–H Bond Activation: Rapid and Regioselective Double Cyclopalladation Monitored by in situ Raman SpectroscopyChemical Communications (2014) 50, 10287. 

12. D. Gracin, V. Štrukil, T, Friščić, I. Halasz, K. Užarević, Laboratory real-time and in situ monitoring of mechanochemical milling reactions using Raman spectroscopyAngew. Chem. Int. Ed.(2014) 53, 6193. 

11. M. Juribašić, I. Halasz, D. Babić, D. Cinčić, J. Plavec, M. Ćurić, Aging and Ball-Milling as Low-Energy and Environmentally-Friendly Methods for the Synthesis of Pd(II) PhotosensitizersOrganometallics, (2014), 33, 1227.

2013

10. T. Friščić, I. Halasz, P. J. Beldon, A. M. Belenguer, F. Adams, S. A. J. Kimber, V. Honkimäki, R. E. Dinnebier, Real-time and in situ monitoring of mechanochemical milling reactionsNature Chem., (2013), 5, 66-73.

09. 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 acidsAngewandte Chemie International Edition (2013), 52, 5504–5508.

08. I. Halasz, A. Puškarić, S. A. J. Kimber, P. J. Beldon, A. M. Belenguer, F. Adams, V. Honkimäki, R. E. Dinneber, B. Patel, W. Jones, V. Štrukil and T. Friščić, Real-Time In Situ Powder X-ray Diffraction Monitoring of Mechanochemical Synthesis of Pharmaceutical CocrystalsAngewandte Chemie International Edition,  (2013), 52, 11538-11541. DOI: 10.1002/anie.201305928.

Hot article; Highlighted as inner cover of the issue.

07. M. Juribašić, A. Budimir, S. Kazazić, M. Ćurić, Dicyclopalladated Complexes of Asymmetrically Substituted Azobenzenes: Synthesis, Kinetics and MechanismsInorganic Chemistry, (2013), 52, 12749.

06. I. Halasz,  S. A. J. Kimber, P. J. Beldon, A. M. Belenguer, F. Adams, V. Honkimäki, R. C. Nightingale, R. E. Dinneber, T. Friščić, In situ and real-time monitoring of mechanochemical milling reactions using synchrotron X-ray diffractionNature Protocols (2013) 8, 1718–1729. doi:10.1038/nprot.2013.100 

2012

05. I. Huskić, I. Halasz, T. Friščić, H. Vančik, Mechanosynthesis of nitrosobenzenes: a proof-of-principle study in combining solvent-free synthesis with solvent-free separations. Green Chemistry. (2012) 14, 1597-1600. 

04. M. Rubčić, K. Užarević, I. Halasz, N. Bregović, M. Mališ, I. Đilović, Z. Kokan, R. S. Stein, R. E. Dinnebier and V. Tomišić, Desmotropy, Polymorphism, and Solid-State Proton Transfer: Four Solid Forms of an Aromatic o-Hydroxy Schiff BaseChemistry - A European Journal (2012)  18, 5620–5631. 

03. I. Halasz, R. E. Dinnebier, T. Chiodo, H. Saxell, Structures of four polymorphs of the pesticide dithianon solved from X-ray powder diffraction data. Acta Crystallographica. Section B, Structural Science. (2012) , 68, 661-666.

2011

02. D. Cinčić,  M. Juribašić, D. Babić, K. Molčanov, P. Šket, J. Plavec, M. Ćurić, New Insight into the Solid-State Molecular Dynamics, Mechanochemical Synthesis of Azobenzene/Triphenylphosphine PalladacyclesChemical Communications, 2011, 47, 11543.

 

2010

01. M. Juribašić, M. Ćurić, K. Molčanov, D. Matković-Čalogović, D. Babić, Unusual Azobenzene/Bipyridine Palladacycles: Structural, Dynamical, Photophysical and Theoretical StudiesDalton Transactions, (2010), 39, 8769. 

2016.–2019. Croatian Science Foundation Starting Grant "Mechanochemical reactivity under controlled temperature and atmosphere for clean synthesis of functional materials", PI dr. sc. Krunoslav Užarević. (UIP-2014-09-4744)

2015.-2019. Croatian Science Foundation Investigator Grant, "Green synthesis of organopalladium photosensitizers", PI dr. sc. Manda Ćurić.

2015.-2016. Bilateral project with BAM Federal Institute for Materials Research and Testing, Germany "Simultaneous synchrotron X-ray powder diffraction and Raman spectroscopy monitoring of mechanochemical reactions in situ and in real time", PIs dr. sc. Krunoslav Užarević and dr. sc. Franciska Emmerling (BAM Berlin).

2014.-2016. FP-7-People-NEWFELPRO Fellowship, Grant 62, for research in the Friščić Group,  McGill University, Montreal, Canada. PI Krunoslav Užarević

2014.-2016. Bilateral project with Slovenija , "Tri pristupa sintezi dipaladiranih azobenzena s fosfinskim bočnim ligandima", PIs dr. sc. Marina Juribašić Kulcsar i dr. sc. Primož Šket. 

2014. Croatian Agency for SMEs, Innovations and Investments (BICRO) project „Development of solvent-free synthesis of pharmaceutically active ingredient“, PI dr. sc. Ivan Halasz (PoC-11-5). 

2014-2015. Grant of Croatian Academy of Sciences and Arts for project “Development of Raman spectroscopic methodology for direct and in situ monitoring of mechanochemical reactions". PI dr. sc. Krunoslav Užarević.

2012-2013 EU-FP7-Project "East-NMR" for NMR Access to SLONMR-NIC , "NMR Study of Pd(II) and Pt(II) Cyclometallated Complexes of Azobenzenes", Group leader for access to NMR facility dr. sc. Manda Ćurić (Grant number 228461P, EU FP7 ).

2010-2013. Ministry of Science, Education and Sports Grant "Design, synthesis and properties of organic ligands and their metal complexes", PI dr. sc. Manda Ćurić. (br. projekta 098-0982915-2960)