IP-2019-04-9560

Trajanje:

1. 2. 2020. – 31. 1. 2024.

Financiranje / Funding

HRVATSKA ZAKLADA ZA ZNANOST / CROATIAN SCIENCE FOUNDATION

VODITELJ PROJEKTA / PRINCIPAL INVESTIGATOR: prof. dr. sc. Vladislav Tomišić

INSTITUCIJE KOJE SUDJELUJU U PROJEKTU / INSTITUTIONS

Prirodoslovno-matematički fakultet, Sveučilište u Zagrebu

Kemijsko-tehnološki fakultet, Sveučiliste u Splitu

Kemijski odsjek, Sveučilište u Milanu

Faculty of Science, University of Zagreb

Faculty of Chemistry and Technology, University of Split

Department of Chemistry, University of Milan

NAZIV PROJEKTA / PROJECT TITLE

Koordinacijske reakcije makrocikličkih liganada u otopini

Coordination Reactions of Macrocyclic Ligands in Solution

SAŽETAK / ABSTRACT

Od samih početaka supramolekulske kemije, istraživanja makrocikličkih spojeva od posebne su važnosti za njezin razvoj. Naime, takvi spojevi često tvore izrazito stabilne komplekse te su ponekad izrazito selektivni prema određenoj kemijskoj vrsti, što je posljedica njihovog dobro definiranog i relativno rigidnog veznog mjesta. Projekt MacroSol fokusirat će se na dizajn i pripravu različitih makrocikličkih liganada (kaliksarena, kukurbiturila, ciklodekstrina i ciklopeptida) i opširno fizikalno-kemijsko istraživanje njihovog potencijala kao receptora kationa, aniona i neutralnih vrsta. Pri tome će naglasak biti stavljen na fluorescentne receptore te one topljive u vodi, kao i na proučavanje reakcija kompleksiranja koje su posljedica solvofobnih interakcija. Termodinamika koordinacijskih reakcija istražit će se brojnim eksperimentalnim metodama, kao što su mikrokalorimetrija, spektrofotometrija, spektroskopija NMR, spektrofluorimetrija, potenciometrija i konduktometrija. Važan cilj projekta jest razumijevanje utjecaja solvatacije na promatrane ravnoteže, zbog čega će se reakcije kompleksiranja proučavati u više različitih otapala. Taj će se aspekt dodatno istražiti određivanjem termodinamičkih funkcija otapanja istraživanih liganada i kompleksa te njihovog transfera iz jednog otapala u drugo. Uvid u strukturne karakteristike liganada i kompleksa dobit će se na temelju rezultata eksperimenata NMR,  a odredit će se i odgovarajuće kristalne strukture pomoću rentgenske difrakcije na jediničnim kristalima. Metode računalne kemije (DFT, MD) upotrijebit će se da bi se istražile strukture receptora i konformacijske promjene do kojih dolazi uslijed kompleksiranja iona i stvaranja inkluzijskih kompleksa. Te će tehnike također pripomoći interpretaciji eksperimentalnih rezultata.  Očekuje se da će saznanja proizašla iz istraživanja predloženih u okviru projekta pružiti detaljan uvid u povezanost receptorskih svojstava i strukturnih karakteristika makrocikala,  što će omogućiti daljnji razvoj spojeva koji mogu učinkovito i selektivno vezati ione i neutralne vrste.

Since the beginning of the research in the field of supramolecular chemistry, macrocycles have received great attention and played a key role in its development. That has been due to their capacity to form well-defined binding sites, from which the high affinity towards particular chemical species and the corresponding peak selectivity originate. The MacroSol project will focus on the design and preparation of diverse macrocyclic hosts (calixarenes, cucurbiturils, cyclodextrins, and cyclopeptides) and comprehensive physicochemical studies of their potential as coordinating agents for different charged and neutral species. Particular emphasis will be placed on fluorescent receptors, as well as water-soluble ones, and on the solvophobically driven complexation reactions. Thermodynamics of coordination reactions will be studied by a number of experimental techniques, namely ITC, UV-Vis and NMR spectroscopies, spectrofluorimetry, potentiometry, and conductometry. An important aim of the project, i.e. the understanding of the solvent effects on the studied processes, will be achieved by investigating the thermodynamics of complexation reactions in different media. This subject will be additionally explored by the determination of solution and transfer thermodynamic functions of the receptors and their complexes. An insight into the structural characteristics of the ligands and complexes will be gained by means of NMR spectroscopy and crystal structure determination by X-ray diffraction. Molecular dynamics simulations and DFT calculations will also be used to explore structures of the studied compounds and conformational changes taking place upon ion binding and formation of inclusion complexes. The computational techniques will also aid the interpretation of the results obtained experimentally. It is expected that the information gathered in the course of a project implementation will significantly contribute to a better understanding of the structure-reactivity relationships, which could be of great importance in targeted design of the compounds capable of efficient and selective binding of ions and neutral species.

PROJEKTNI TIM / PROJECT TEAM

PMF, Sveučilište u Zagrebu / Faculty of Science, University of Zagreb: Branimir Bertoša, Nikola Bregović, Nikola Cindro, Marija Cvetnić, Gordan Horvat, Matija Modrušan, Katarina Leko, Katarina Pičuljan, Josip Požar, Vladislav Tomišić, Andrea Usenik

KTF, Sveučiliste u Splitu / Faculty of Chemistry and Technology, University of Split: Renato Tomaš, Marina Tranfić Bakić

Odjel za kemiju, Sveučilište u Milanu / Department of Chemistry, University of Milan: Giovanna Speranza

PUBLIKACIJE / PUBLICATIONS

1. K. Leko, M. Hanževački, Z. Brkljača, K. Pičuljan, R. Ribić, J. Požar, Solvophobically Driven Complexation of Adamantyl Mannoside with β‐Cyclodextrin in Water and Structured Organic Solvents // Chemistry : a European Journal 26 (2020), 23; 5208−5219.
   (rad istaknut na naslovnici časopisa)
2. N. Vidović, G. Horvat, D. Riva, T. Rinkovec, N. Cindro, V. Tomišić, G. Speranza, Chloride-Assisted Peptide Macrocyclization // Organic Letters 22 (2020), 6; 2129−2134.
3. D. Barišić, N. Cindro, N. Vidović, N. Bregović, V. Tomišić, Protonation and anion-binding properties of aromatic sulfonylurea derivatives // RSC Advances 11 (2021) 23992−24000.
4. G. Horvat, S. Tarana, N. Vidović, N. Cindro, G. Speranza, V. Tomišić, Thermodynamic and MD studies of anion complexation by cyclopentaleucine in acetonitrile and dimethyl sulfoxide // Journal of Molecular Liquids 340 (2021) 116848.
5. J. Požar, M. Cvetnić, A. Usenik, N. Cindro, G. Horvat, K. Leko, M. Modrušan, V. Tomišić, The Role of Triazole and Glucose Moieties in Alkali Metal Cation Complexation by Lower-Rim Tertiary-Amide Calix[4]arene Derivatives // Molecules 27 (2022) 470.
6. D. Barišić, F. Lešić, M. Tireli Vlašić, K. Užarević, N. Bregović, V. Tomišić, Anion binding by receptors containing NH donating groups - What do anions prefer? // Tetrahedron 120 (2022) 132875.
7. M. Alešković, S. Roca, R. Jozepović, N. Bregović, M. Šekutor, Unravelling Binding Effects in Cyclodextrin Inclusion Complexes with Diamondoid Ammonium Salt Guests // New Journal of Chemistry 46 (2022) 13406−13414.
   (rad istaknut na naslovnici časopisa)
8. I. Petters, M. Modrušan, N. Vidović, I. Crnolatac, N. Cindro, I. Piantanida, G. Speranza, G. Horvat, V. Tomišić, Anion-Sensing Properties of Cyclopentaphenylalanine // Molecules 27 (2022) 3918.
9. A. Usenik, K. Leko, V. Petrović Peroković, Ž. Car, R. Ribić, K. Pičuljan, M. Hanževački, J. Draženović, J. Požar, Hydrophobically driven hosting – What about the guest? // Journal of Molecular Liquids 388 (2023) 122774.
10. A. Usenik, M. Alešković, S. Roca, I. Markuš, M. Šekutor, J. Požar, Hosting of diamantane alcohols in water and hydrogen-bonded organic solvents: the (non-)classical hydrophobic effect // New Journal of Chemistry 47 (2023) 18745-18755.
11. L. Kumar, S. G. Dash,  K. Leko, D. Trzybiński, N. Bregović, D. Cinčić, M. Arhangelskis, Elucidating mechanochemical reactivity of a ternary halogen-bonded cocrystal system by computational and calorimetric studies // Physical Chemistry Chemical Physics 42 (2023), accepted for publishing, DOI: 10.1039/d3cp04358d
12. K. Leko, A. Usenik, N. Cindro, M. Modrušan, J. Požar, G. Horvat, V. Stilinović, T. Hrenar, V. Tomišić, Enhancing the Cation-Binding Ability of Fluorescent Calixarene Derivatives: Structural, Thermodynamic, and Computational Studies // ACS Omega (2023) accepted for publishing, DOI: 10.1021/acsomega.3c06509
13. M. Cvetnić, R. Šplajt, E. Topić, M. Rubčić, N. Bregović, Direct thermodynamic characterization of solid-state reactions by isothermal calorimetry // Physical Chemistry Chemical Physics (2023), accepted for publishing, DOI: 10.1039/D3CP03933A
    (rad istaknut u skupu 2023 PCCP HOT Articles)
14. M. Cvetnić, N. Cindro, E. Topić, N. Bregović, V. Tomišić, Supramolecular Handshakes: Characterization of Urea-Carboxylate Interactions Within Calixarene Frameworks // ChemPlusChem (2024), e202400130.
15. M. Modrušan, L. Glazer, L. Otmačić, I. Crnolatac, N. Cindro, N. Vidović, I. Piantanida, G. Speranza, G. Horvat, V. Tomišić, Anion-Binding Properties of Short Linear Homopeptides // Int. J. Mol. Sci. 25 (2024) 5235.
16. M. Cvetnić, N. Cindro, N. Bregović, V. Tomišić, Thermodynamics of Anion Binding by (Thio)ureido-calix[4]arene Derivatives in Acetonitrile // ACS Phys. Chem. Au (2024), DOI: 10.1021/acsphyschemau.4c00077

KONFERENCIJE / CONFERENCES

1. Usenik, Andrea; Leko, Katarina; Hanževački, Marko; Pičuljan, Katarina, Petrović Peroković, Vesna; Car, Željka; Ribić, Rosana; Požar, Josip.
   Melting Down the Iceberg Model: Hydrophobic Cavities and (Sweetened) Alcohols, Adriatic NMR Conference, 22.−24.09.2020., Peroj, Hrvatska.
   POZVANO PREDAVANJE
2. Modrušan, Matija; Cindro, Nikola; Leko, Katarina; Tomišić, Vladislav.
   Synthesis of phenanthridine-based calix[4]arene glycoconjugate and physicochemical characterization of its complexation reactions with alkali metal cations, Adriatic NMR Conference, 22.−24.09.2020., Peroj, Hrvatska.
3. Alešković, Marija; Jozepović, Ruža; Roca, Sunčica; Bregović, Nikola; Šekutor, Marina.
   Synthesis and Binding of Permethylated Diamondoid Ammonium Salts, Adriatic NMR Conference, 22.−24.09.2020., Peroj, Hrvatska.
   POZVANO PREDAVANJE
4. Usenik, Andrea; Leko, Katarina; Hanževački, Marko; Pičuljan, Katarina, Petrović Peroković, Vesna; Car, Željka; Požar, Josip.
   From Icebergs to Geysers: The Story behind Hydrophobic Effect, 5^th Faculty of Science PhD Student Symposium, 24.−25.04.2021., Zagreb, Hrvatska.
   PREDAVANJE
5. Požar, Josip; Cvetnić, Marija; Cindro, Nikola; Usenik, Andrea; Leko, Katarina; Modrušan, Matija; Tomišić, Vladislav.
   Alkali-metal cation coordination to calix[4]arenes containing triazole functionalities, 6^th Central and Eastern European Conference on Thermal Analysis and Calorimetry & 15^th Mediterranean Conference on Calorimetry and Thermal Analysis, 20.−24.07.2021., Split, Hrvatska.
   PREDAVANJE 
6. Bregović, Nikola; Barišić, Dajana; Cindro, Nikola; Vidović, Nikolina; Užarević, Krunoslav; Tireli, Martina; Lešić, Filip; Tomišić, Vladislav.
   Receptors Based on Sulfonylurea and Amide Functional Groups - Newcomers and Veterans in Anion-coordination Chemistry, Adriatic NMR Conference, 13.−15.09.2021., Primošten, Hrvatska.
   POZVANO PREDAVANJE
7. Leko, Katarina; Usenik, Andrea; Babić, Tea; Modrušan, Matija; Požar, Josip; Tomišić, Vladislav.
   Fluorescent Phenanthridine-based Calix[4]arene Derivatives: Synthesis and Thermodynamics of Complexation Reactions with Metal Cations, Adriatic NMR Conference, 13.−15.09.2021., Primošten, Hrvatska.
   PREDAVANJE
8. Usenik, Andrea; Markuš, Iva; Pičuljan, Katarina; Alešković, Marija; Šekutor, Marina; Požar, Josip.
   Diamantanes are a Hydrophobic Cavity's Best Friend: The Role of Solvent Structuring in Complex Stability, Adriatic NMR Conference, 13.−15.09.2021., Primošten, Hrvatska
9. Usenik, Andrea; Poljanić, Leon; Radonić, Doroteja; Pičuljan, Katarina; Car, Željka; Petrović Peroković, Andrea; Požar, Josip.
   Exploring the Bright Side of Hydrophobically Driven Complexation: The Bitter Synthesis of Sweet Fluorescent Amphiphiles, Adriatic NMR Conference, 13.−15.09.2021., Primošten, Hrvatska.
10. Cvetnić, Marija; Cindro, Nikola; Bregović, Nikola; Tomišić, Vladislav.
    Exploring Protonation Properties of Calix[4]arenes bearing Urea Moieties and their Affinities towards Anions in Acetonitrile, Adriatic NMR Conference, 13.−15.09.2021., Primošten, Hrvatska
11. Modrušan, Matija; Divjak, Toni; Vidović, Nikolina; Cindro, Nikola; Speranza, Giovanna; Horvat, Gordan; Tomišić, Vladislav.
    Thermodynamic and Structural Studies of Anion Binding by Linear Penta-homopeptides, Adriatic NMR Conference, 13.−15.09.2021., Primošten, Hrvatska
12. Požar, Josip.
    THE SOLVENT EFFECT ON THE HOST-GUEST COMPLEXATION EQUILIBRIA; THE GOOD AND THE BAD, 27^th Croatian Meeting of Chemists and Chemical Engineers, 5.−8.10.2021., Veli Lošinj, Hrvatska
    POZVANO PREDAVANJE
13. Usenik, Andrea; Poljanić, Leon; Radonić, Doroteja; Pičuljan, Katarina; Car, Željka; Petrović Peroković, Vesna; Požar, Josip.
    SHINING A LIGHT ON HYDROPHOBICALLY DRIVEN COMPLEXATION: THE BITTERSWEET STORY BEHIND FLUORESCENT MANNOCONJUGATES, 27^th Croatian Meeting of Chemists and Chemical Engineers, 5.−8.10.2021., Veli Lošinj, Hrvatska
    PREDAVANJE
14. Horvat, Gordan.
    SIMULTANEOUS REGRESSION ANALYSIS OF TITRATION DANA OBTAINED BY SEVERAL ANALYTICAL METHODS, 27^th Croatian Meeting of Chemists and Chemical Engineers, 5.−8.10.2021., Veli Lošinj, Hrvatska.
15. Horvat, Gordan; Petters, Ivan; Jakuš, Ivana; Vidović, Nikolina; Cindro, Nikola; Speranza, Giovanna; Tomišić, Vladislav.
    ANION BINDING PROPERTIES OF TWO PENTAMERIC HOMOCYCLOPEPTIDES IN ACETONITRILE AND METHANOL, 27^th Croatian Meeting of Chemists and Chemical Engineers, 5.−8.10.2021., Veli Lošinj, Hrvatska.
16. Modrušan, Matija; Tomaš, Renato; Glazer, Lucija; Cindro, Nikola; Leko, Katarina; Tomišić, Vladislav.
    THERMODYNAMICS OF COMPLEXATION OF ALKALI AND ALKALINE EARTH METAL CATIONS BY A PHENANTHRIDINE-BASED CALIX[4]ARENE GLYCOCONJUGATE, 27^th Croatian Meeting of Chemists and Chemical Engineers, 5.−8.10.2021., Veli Lošinj, Hrvatska.
17. Modrušan, Matija; Divjak, Toni; Vidović, Nikolina; Cindro, Nikola; Speranza, Giovanna; Horvat, Gordan; Tomišić, Vladislav.
    ANION BINDING AFFINITIES OF LINEAR PENTA-HOMOPEPTIDES IN SOLUTION, 27^th Croatian Meeting of Chemists and Chemical Engineers, 5.−8.10.2021., Veli Lošinj, Hrvatska.
18. Markuš, Iva; Usenik, Andrea; Pičuljan, Katarina; Alešković, Marija; Šekutor, Marina; Požar, Josip.
    DIAMANTANE ALCOHOLS AND HYDROPHOBIC CAVITIES: THE PERFECT PAIR ALSO IN NON-AQUEOUS SOLUTION?, 27^th Croatian Meeting of Chemists and Chemical Engineers, 5.−8.10.2021., Veli Lošinj, Hrvatska.
19. Cvetnić, Marija; Cindro, Nikola; Bregović, Nikola; Tomišić, Vladislav.
    CALIX[4]ARENES BEARING UREA MOIETIES - INVESTIGATION OF SUPRAMOLECULAR BEHAVIOUR, 27^th Croatian Meeting of Chemists and Chemical Engineers, 5.−8.10.2021., Veli Lošinj, Hrvatska.
20. Leko, Katarina; Usenik, Andrea; Vianello, Robert; Hok, Lucija; Tomišić, Vladislav.
    THERMODYNAMIC AND STRUCTURAL STUDIES OF COMPLEXATION REACTIONS OF PHENANTHRIDINE-BASED CALIX[4]ARENE DERIVATIVE WITH ALKALINE EARTH METAL CATIONS, 27^th Croatian Meeting of Chemists and Chemical Engineers, 5.−8.10.2021., Veli Lošinj, Hrvatska.
21. Babić, Tea; Leko, Katarina; Usenik, Andrea; Modrušan, Matija; Jakupec, Nikola; Uran, Erik; Tomišić, Vladislav.
    COMPLEXATION OF TRANSITION METAL CATIONS BY A LOWER-RIM PHENANTHRIDINE CALIX[4]ARENE DERIVATIVES, 27^th Croatian Meeting of Chemists and Chemical Engineers, 5.−8.10.2021., Veli Lošinj, Hrvatska.
22. Alešković, Marija; Roca, Sunčica; Bregović, Nikola; Šekutor, Marina.
    Supramolecular Chemistry of Diamondoid Ammonium Salts, IV Symposium on Supramolecular Chemistry, 10.12.2021., Zagreb, Hrvatska.
    PREDAVANJE
23. Usenik, Andrea.
    Hydrophobic Effect and Beyond, IV Symposium on Supramolecular Chemistry, 10.12.2021., Zagreb, Hrvatska.
    PREDAVANJE
24. Babić, Tea; Topić, Magda; Poljanić, Leon; Usenik, Andrea; Požar, Josip.
    (A) Romantic Relationship Between Hydrophobic Cavities and Aromatic Alcohols, IV Symposium on Supramolecular Chemistry, 10.12.2021., Zagreb, Hrvatska.
25. Markuš, Iva; Usenik, Andrea; Pičuljan, Katarina; Alešković, Marija; Šekutor, Marina; Požar, Josip.
    Diamantane Alcohols and Hydrophobic Cavities: The (not so) Perfect Match in Water and Structured Organic Solvents, IV Symposium on Supramolecular Chemistry, 10.12.2021., Zagreb, Hrvatska.
26. Petters, Ivan; Modrušan, Matija; Vidović, Nikolina; Speranza, Giovanna; Cindro, Nikola; Horvat, Gordan; Tomišić, Vladislav.
    CYCLOPENTAPHENYLALANINE AS A FLUORESCENT ANION SENSOR IN SOLUTION, IV Symposium on Supramolecular Chemistry, 10.12.2021., Zagreb, Hrvatska.
27. Babić, Tea; Usenik, Andrea; Požar, Josip.
    WHEN HYDROPHOBIC CAVITIES MEET BENZENE DERIVATIVES, XIV. susret mladih kemijskih inženjera, 24.−25.2.2022., Zagreb, Hrvatska.
28. Markuš, Iva; Usenik, Andrea; Alešković, Marija; Šekutor, Marina; Požar, Josip.
    HYDROPHOBIC CAVITIES AND DIAMANTANES, XIV. susret mladih kemijskih inženjera, 24.−25.2.2022., Zagreb, Hrvatska.
29. Topić, Magda; Poljanić, Leon; Usenik, Andrea; Požar, Josip.
    HYDROPHOBIC EFFECT - COMPARISON OF AROMATIC AND ALIPHATIC ALCOHOLS, XIV. susret mladih kemijskih inženjera, 24.−25.2.2022., Zagreb, Hrvatska.
30. Usenik, Andrea.
    H₂O vs. D₂O: THERMODYNAMICS BEYOND NMR, Magnetic Moments in Central Europe 2022, 1.−4.6.2022., Primošten, Hrvatska
    POZVANO PREDAVANJE
31. Babić, Tea; Usenik, Andrea; Pičuljan, Katarina; Bedeković, Nikola, Požar, Josip.
    UNDERSTANDING THE ATTRACTION BETWEEN HYDROPHOBIC CAVITIES AND BENZENE DERIVATIVES, Magnetic Moments in Central Europe 2022, 1.−4.6.2022., Primošten, Hrvatska
32. Modrušan, Matija; Otmačić, Lucija; Glazer, Lucija; Vidović, Nikolina; Cindro, Nikola; Speranza, Giovanna; Horvat, Gordan; Tomišić, Vladislav.
    ANION BINDING BY LINEAR PENTA–HOMOPEPTIDES COMPRISED OF AMINO ACIDS WITH NONPOLAR SIDE CHAINS, Magnetic Moments in Central Europe 2022, 1.−4.6.2022., Primošten, Hrvatska
33. Usenik, Andrea; Leko, Katarina; Petrović Peroković, Vesna; Car, Željka; Ribić, Rosana; Pičuljan, Katarina; Hanževački, Marko; Požar, Josip.
    THE THERMODYNAMICS OF HYDROPHOBICALY DRIVEN INCLUSION; β-CYCLODEXTRIN VS. CUCURBIT[7]URIL, Magnetic Moments in Central Europe 2022, 1.−4.6.2022., Primošten, Hrvatska
34. Ernečić, Amalija; Roca, Sunčica; Bregović, Nikola; Lazarenko, Viktoriia; Šekutor, Marina; Alešković, Marija.
    ADAMANTANE AMMONIUM SALTS AS GUESTS FOR THE CYCLODEXTRIN HOST: SOMETHING OLD, SOMETHING NEW, Magnetic Moments in Central Europe 2022, 1.−4.6.2022., Primošten, Hrvatska
35. Roca, Sunčica; Ernečić, Amalija; Višić, Nikolina; Alešković, Marija; Bregović, Nikola; Šekutor, Marina.
    EXPLORING STRUCTURAL AND THERMODYNAMIC PROPERTIES OF VARIOUS DIAMANTANE AMINE–CYCLODEXTRIN COMPLEXES, Magnetic Moments in Central Europe 2022, 1.−4.6.2022., Primošten, Hrvatska
36. Modrušan, Matija.
    The binding of anions on linear and cyclic homopeptides, BioExcel Summer School on Biomolecular Simulations 2022, 12.-17.6.2022., Pula, Italija
37. Usenik, Andrea.
    THE CHALLENGES BEHIND SOLUTIONS: AN INSIGHT FROM VARIOUS VIEWPOINTS OF SUPRAMOLECULAR PHYSICAL CHEMISTS, Mini-simpozij Hrvatskog kemijskog društva Rijeka 2022., 4.7.2022., Rijeka, Hrvatska
    POZVANO PREDAVANJE
38. Cvetnić, Marija; Bregović, Nikola; Cindro, Nikola; Tomišić, Vladislav.
    Shaking Ureido and Carboxylic Hands – Calixarenes Uniting, Calix 2022, 10.−14. 7. 2022., New Orleans, SAD
39. Duvnjak, Mirko.
    SINTEZA I MAKROCIKLIZACIJA OLIGOPEPTIDA, 28. 9. 2022., Ceremonija dodjele Rektorove nagrade Sveučilišta u Zagrebu za akademsku godinu 2021./2022., Zagreb, Hrvatska
40. Otmačić, Lucija; Modrušan, Matija; Vidović, Nikolina; Cindro, Nikola; Crnolatac, Ivo; Speranza, Giovanna; Tomišić, Vladislav; Horvat, Gordan.
    Kompleksiranje aniona s metilnim esterom pentafenilalanina u acetonitrilu, 7. Simpozij studenata kemičara, 22. 10. 2022., Zagreb, Hrvatska
41. Cvetnić, Marija; Mendeš, Davor; Bregović, Nikola; Tomišić, Vladislav.
    Thermodynamics of Several Ion-Pairings in Acetonitrile, Solutions in Chemistry 2022, 8.−11. 11. 2022., Sveti Martin na Muri, Hrvatska
42. Babić, Tea; Usenik, Andrea; Pičuljan, Katarina; Bedeković, Nikola; Požar, Josip.
    Complexation Thermodynamics of Benzene Derivatives with Macrocyclic Receptors, Solutions in Chemistry 2022, 8.−11. 11. 2022., Sveti Martin na Muri, Hrvatska
43. Modrušan, Matija; Otmačić, Lucija; Vidović, Nikolina; Cindro, Nikola; Crnolatac, Ivo; Speranza, Giovanna; Horvat, Gordan; Tomišić, Vladislav.
    Thermodynamics of Anion Binding by Pentaphenylalanine in Acetonitrile, Solutions in Chemistry 2022, 8.−11. 11. 2022., Sveti Martin na Muri, Hrvatska
44. Cvetnić, Marija; Šplajt, Robert; Topić, Edi; Bregović, Nikola.
    Direct Measurement of Heat Effects for Solid-State Reactions by Isothermal Calorimetry, V. Symposium on Supramolecular Chemistry, 8. 12. 2022., Zagreb, Hrvatska
45. Glazer, Lucija; Modrušan, Matija; Vidović, Nikolina; Cindro, Nikola; Speranza, Giovanna; Tomišić, Vladislav; Horvat, Gordan.
    THERMODYNAMIC AND STRUCTURAL STUDIES ON THE COMPLEXATION OF METHYL ESTER OF PENTAISOLEUCINE WITH ANIONS IN ACETONITRILE, V. Symposium on Supramolecular Chemistry, 8. 12. 2022., Zagreb, Hrvatska
46. Duvnjak, Mirko; Talajić, Gregor; Modrušan, Matija; Horvat, Gordan; Cindro, Nikola; Tomišić, Vladislav.
    SYNTHESIS OF GLYCINE AND PHENYLALANINE CONTAINING CYCLOPEPTIDES AND THEIR ANION BINDING PROPERTIES IN ACETONITRILE, V. Symposium on Supramolecular Chemistry, 8. 12. 2022., Zagreb, Hrvatska
47. Babić, Tea; Usenik, Andrea; Pičuljan, Katarina; Bedeković, Nikola; Požar, Josip.
    Macrocyclic Receptors and Benzene Derivatives: Complexation Thermodynamics and Substituent Impact, V. Symposium on Supramolecular Chemistry, 8. 12. 2022., Zagreb, Hrvatska
48. Modrušan, Matija; Petrović Hađar, Emilija; Glazer, Lucija; Duvnjak, Mirko; Vidović, Nikolina; Cindro, Nikola; Speranza, Giovanna; Tomišić, Vladislav; Horvat, Gordan.
    Affinity of Linear and Cyclic Peptides Towards Bivalent Cations, 28th Croatian Meeting of Chemists and Chemical Engineers, 28.−31. 3. 2023., Rovinj, Hrvatska
49. Cvetnić, Marija; Bregović, Nikola; Cindro, Nikola; Tomišić, Vladislav.
    UREIDO-CALIX[4]ARENE DERIVATIVES IN THE ROLE OF HOSTS FOR ANIONS, ION-PAIRS AND/OR DIACETATOCALIX[4]ARENES, The Adriatic NMR Conference 2023, 1.−4. 6. 2023., Mali Ston, Hrvatska
    PREDAVANJE
50. Modrušan, Matija.
    PEPTIDES AS VERSATILE ION-BINDING RECEPTORS, The Adriatic NMR Conference 2023, 1.−4. 6. 2023., Mali Ston, Hrvatska
    PREDAVANJE
51. Kukina Gradečak, Karla; Leko, Katarina; Usenik, Andrea; Cindro, Nikola; Tomišić, Vladislav.
    COMPLEXATION OF ALKALI AND ALKALINE EARTH METAL CATIONS BY CALIX[6]ARENE RECEPTORS, The Adriatic NMR Conference 2023, 1.−4. 6. 2023., Mali Ston, Hrvatska
52. Fotović, Luka; Usenik, Andrea; Babić, Tea; Bedeković, Nikola; Pičuljan, Katarina; Požar, Josip.
    COMPLEXATION THERMODYNAMICS OF BENZENE DERIVATIVES WITH CUCURBIT[7]URIL AND β-CYCLODEXTRIN, The Adriatic NMR Conference 2023, 1.−4. 6. 2023., Mali Ston, Hrvatska
53. Požar, Josip ; Usenik, Andrea ; Alešković, Marija ; Roca, Sunčica ; Mrkuš, Iva ; Šekutor, Marina.
    COMPARATIVE STUDY OF CYCLODEXTRIN BINDING AFFINITIES FOR DIAMONDOID ALCOHOLS, The Adriatic NMR Conference 2023, 1.−4. 6. 2023., Mali Ston, Hrvatska
54. Lucija Otmačić.
    KOMPLEKSIRANJE ANIONA S METILNIM ESTEROM PENTAFENILALANINA U ACETONITRILU, 29. 6. 2023., Ceremonija dodjele Rektorove nagrade Sveučilišta u Zagrebu za akademsku godinu 2022./2023., Zagreb, Hrvatska
55. Tomišić, Vladislav.
    SUPRAMOLEKULSKI RECEPTORI: TERMODINAMIKA I STRUKTURA, Simpozij Hrvatskog kemijskog društva Rijeka 2023, 7. 7. 2023., Rijeka, Hrvatska.
    POZVANO PREDAVANJE
56. Horvat, Gordan
    On the Interface between Experiment and Computation, the Experimentalist's Viewpoint, Computational Chemistry Day 2023, 15.−16. 9. 2023., Zagreb, Hrvatska
    PREDAVANJE
57. Petranović, Ivan; Horvat, Gordan.
    Molecular Dynamics Simulations of Selected Homocyclopentapeptides with Chloride, Bromide and Iodide Anions, Computational Chemistry Day 2023, 15.−16. 9. 2023., Zagreb, Hrvatska
58. Modrušan, Matija; Otmačić, Lucija; Glazer, Lucija; Vidović, Nikolina; Cindro, Nikola; Speranza, Giovanna; Tomišić, Vladislav; Horvat, Gordan.
    THERMODYNAMIC AND STRUCTURAL CHARACTERIZATION OF LINEAR PEPTIDE COMPLEXES WITH SIMPLE IONS IN SOLUTION, Peptide Chemistry Day 2023, 20. 9. 2023., Zagreb, Hrvatska
59. Petrović Hađar, Emilija; Modrušan, Matija; Duvnjak, Mirko; Cindro, Nikola; Tomišić, Vladislav; Horvat, Gordan.
    THERMODYNAMIC AND STRUCTURAL CHARACTERIZATION OF CYCLOPEPTIDE COMPLEXES WITH DIFFERENT IONS IN ACETONITRILE, Peptide Chemistry Day 2023, 20. 9. 2023., Zagreb, Hrvatska
60. Horvat, Gordan; Otmačić, Lucija; Modrušan, Matija; Vidović, Nikolina; Cindro, Nikola; Speranza, Giovanna; Tomišić, Vladislav.
    THERMODYNAMIC AND STRUCTURAL CHARACTERIZATION OF CYCLOPEPTIDE COMPLEXES WITH COLORIMETRIC AND FLUORESCENT ANIONIC DYES, Peptide Chemistry Day 2023, 20. 9. 2023., Zagreb, Hrvatska
61. Vidović, Nikolina; Horvat, Gordan; Riva, Davide; Rinkovec, Tamara; Cindro, Nikola; Tomišić, Vladislav; Speranza, Giovanna.
    CHLORIDE-ASSISTED PEPTIDE MACROCYCLIZATION, Peptide Chemistry Day 2023, 20. 9. 2023., Zagreb, Hrvatska
62. Kukina Gradečak, Karla; Leko, Katarina; Usenik, Andrea; Cindro, Nikola; Tomišić, Vladislav.
    INFLUENCE OF CATION BINDING ON INTRINSIC FLUORESCENCE OF TERTIARY-AMIDE CALIX[6]ARENE DERIVATIVE, 8. Simpozij studenata kemičara, 21. 10. 2023., Zagreb, Hrvatska
    PREDAVANJE
63. Kukina Gradečak, Karla; Leko, Katarina; Usenik, Andrea; Cindro, Nikola; Tomišić, Vladislav.
    THERMODYNAMICS OF CATION-BINDING REACTIONS OF TERTIARY-AMIDE CALIX[6]ARENE DERIVATIVE, VI. Symposium on Supramolecular Chemistry, 6. 12. 2023., Zagreb, Hrvatska
64. J. Požar, A. Usenik, M. Šekutor, K. Leko, M. Alešković, R. Ribić, V. Petrović Peroković, Ž. Car, K. Pičuljan, S. Roca, M. Hanževački, Z. Brkljača.
    THE HYDROPHOBICALLY DRIVEN INCLUSION REVISITED, THE COMPLEXATION OF SIMPLE ALIPHATIC AND AROMATIC COMPOUNDS WITH CYCLODEXTRINS AND CUCURBITURILS, VI. Symposium on Supramolecular Chemistry, 6. 12. 2023., Zagreb, Hrvatska
    POZAVNO PREDAVANJE
65. M. Modrušan.
    Effect of chain length on the affinities of the short linear homopeptides towards ions in solution, VI. Symposium on Supramolecular Chemistry, 6. 12. 2023., Zagreb, Hrvatska
    PREDAVANJE
66. M. Cvetnić, N. Cindro, N. Bregović, V. Tomišić.
    ANION-BINDING COMPETITION BETWEEN P-TERT-BUTYLCALIX[4]ARENE DERIVATIVES: UREA VERSUS THIOUREA, SUMMER CONFERENCE OF CROATIAN CHEMICAL SOCIETY RIJEKA – PULA 2024, 5.−6. 9. 2024., Rijeka, Hrvatska

DIPLOMSKI RADOVI / DIPLOMA OR MASTER THESES

1. Doroteja Lončarić
   Sinteza i fizikalno-kemijska karakterizacija bis-fosfatnih estera
   (10. 7. 2020., voditelj/supervisor: Nikola Bregović)
   Synthesis and physico-chemical characterisation of bis-phosphate esters
2. Matija Modrušan
   Sinteza fenantridinskog glikokonjugata kaliks[4]arena i fizikalno-kemijska karakterizacija njegovih reakcija kompleksiranja kationa alkalijskih metala
   (30. 9. 2020., voditelji/supervisors: Nikola Cindro, Vladislav Tomišić)
   Synthesis of phenanthridine-based calix[4]arene glycoconjugate and physicochemical characterization of its complexation reactions with alkali metal cations
3. Slavica Petrović
   Termodinamika kompleksiranja zemnoalkalijskih kationa s ketonskim derivatom kaliks[4]arena
   (30. 9. 2020., voditelji/supervisors: Josip Požar, Draginja Mrvoš-Sermek)
   Thermodynamics of alkaline-earth metal cation complexation with calix[4]arene ketone derivative
4. Doroteja Radonić
   Priprava policikličkih manokonjugata i njihovo kompleksiranje s β-ciklodekstrinom
   (19. 2. 2021., voditelji/supervisors: Vesna Petrović Peroković, Željka Car)
   Synthesis of polycyclic mannoconjugates and their complexation with β-cyclodextrin
5. Ivan Petters
   Termodinamičko i strukturno istraživanje kompleksiranja ciklopentafenilalanina s anionima u otopini
   (14. 7. 2022., voditelj/supervisor: Gordan Horvat)
   Thermodynamic and structural studies on the complexation of cyclopentaphenylalanine with anions in solution
6. Tea Babić
   Termodinamika kompleksiranja derivata benzena s beta-ciklodekstrinom i kukurbit[7]urilom
   (28. 9. 2022., voditelj/supervisor: Josip Požar)
7. Robert Šplajt
   Razvoj metodologije za izravno izotermno kalorimetrijsko određivanje reakcijskih entalpija procesa u čvrstom stanju
   (24. 2. 2023., voditelj/supervisor: Nikola Bregović)
8. Lucija Glazer
   Termodinamičko i strukturno istraživanje kompleksiranja metilnih estera tetra i heksafenilalanina s anionima u acetonitrilu
   (31. 5. 2023., voditelj/supervisor: Gordan Horvat)
   Thermodynamic and structural studies on the complexation of methyl esters of tetra and hexaphenylalanine with anions in acetonitrile
9. Ivan Petranović
   Simulacije molekulske dinamike kompleksa odabranih homociklopentapeptida s kloridnim, bromidnim i jodidnim anionima
   (11. 12. 2023., voditelj/supervisor: Gordan Horvat)
10. Lucija Otmačić
    Termodinamička i strukturna karakterizacija kompleksa ciklopeptida s kolorimetrijskim i fluorescentnim anionskim bojama
    (16. 12. 2023., voditelj/supervisor: Gordan Horvat)

DOKTORSKI RADOVI / PhD THESES

1. Andrea Usenik
   Termodinamika inkluzijskih reakcija amfifilnih spojeva s ciklodekstrinima i kukurbiturilima
   (20. 12. 2023., voditelj/supervisor: Josip Požar)
   Thermodynamics of inclusion reactions of amphiphilic compounds with cyclodextrins and cucurbiturils

NAGRADE I PRIZNANJA / AWARDS

1. Matija Modrušan
   Termodinamika kompleksiranja alkalijskih i zemnoalkalijskih kationa s ketonskim derivatom kaliksarena
   (16. 10. 2020., voditelj: Josip Požar)
   Thermodynamics of alkali and alkaline-earth cation complexation with calix[4]arene ketone derivative
   REKTOROVA NAGRADA / RECTOR'S AWARD
2. Babić, Tea; Topić, Magda; Poljanić, Leon; Usenik, Andrea; Požar, Josip.
   (A) Romantic Relationship Between Hydrophobic Cavities and Aromatic Alcohols, IV Symposium on Supramolecular Chemistry, 10.12.2021., Zagreb, Hrvatska.
   NAGRADA ZA NAJBOLJI POSTER / BEST POSTER PRIZE
3. Topić, Magda; Poljanić, Leon; Usenik, Andrea; Požar, Josip.
   HYDROPHOBIC EFFECT - COMPARISON OF AROMATIC AND ALIPHATIC ALCOHOLS, XIV. susret mladih kemijskih inženjera, 24.−25.2.2022., Zagreb, Hrvatska.
   2. NAGRADA ZA NAJBOLJI POSTER / 2^nd BEST POSTER PRIZE
4. Babić, Tea; Usenik, Andrea; Pičuljan, Katarina; Bedeković, Nikola, Požar, Josip.
   UNDERSTANDING THE ATTRACTION BETWEEN HYDROPHOBIC CAVITIES AND BENZENE DERIVATIVES, Magnetic Moments in Central Europe 2022, 1.−4.6.2022., Primošten, Hrvatska
   NAGRADA ZA NAJBOLJI POSTER / BEST POSTER PRIZE
5. Cvetnić, Marija; Bregović, Nikola; Cindro, Nikola; Tomišić, Vladislav.
   Shaking Ureido and Carboxylic Hands – Calixarenes Uniting, Calix 2022, 10.−14. 7. 2022., New Orleans, SAD
   TRAWEL AWARD
6. Duvnjak, Mirko; Talajić, Gregor; Modrušan, Matija; Horvat, Gordan; Cindro, Nikola; Tomišić, Vladislav.
   SYNTHESIS OF GLYCINE AND PHENYLALANINE CONTAINING CYCLOPEPTIDES AND THEIR ANION BINDING PROPERTIES IN ACETONITRILE, V. Symposium on Supramolecular Chemistry, 8. 12. 2022., Zagreb, Hrvatska
   NAGRADA ZA NAJBOLJI POSTER / BEST POSTER PRIZE
7. Mirko Duvnjak
   SINTEZA I MAKROCIKLIZACIJA OLIGOPEPTIDA
   (2022., voditelj: Nikola Cindro)
   SYNTHESIS AND MACROCYCILIZATION OF OLIGOPEPTIDES
   REKTOROVA NAGRADA / RECTOR'S AWARD
8. Kukina Gradečak, Karla; Leko, Katarina; Usenik, Andrea; Cindro, Nikola; Tomišić, Vladislav.
   COMPLEXATION OF ALKALI AND ALKALINE EARTH METAL CATIONS BY CALIX[6]ARENE RECEPTORS, The Adriatic NMR Conference 2023, 1.−4. 6. 2023., Mali Ston, Hrvatska
   NAGRADA ZA NAJBOLJI POSTER / BEST POSTER PRIZE
9. Lucija Otmačić
   KOMPLEKSIRANJE ANIONA S METILNIM ESTEROM PENTAFENILALANINA U ACETONITRILU
   (29. 06. 2023., voditelj: Gordan Horvat)
   ANION COMPLEXATION BY PENTAPHENYLALANINE METHYL ESTER IN ACETONITRILE
   REKTOROVA NAGRADA / RECTOR'S AWARD
10. Petrović Hađar, Emilija; Modrušan, Matija; Duvnjak, Mirko; Cindro, Nikola; Tomišić, Vladislav; Horvat, Gordan. 
    THERMODYNAMIC AND STRUCTURAL CHARACTERIZATION OF CYCLOPEPTIDE COMPLEXES WITH DIFFERENT IONS IN ACETONITRILE, Peptide Chemistry Day 2023, 20.9.2023., Zagreb, Hrvatska
    NAGRADA ZA NAJBOLJI POSTER / BEST POSTER PRIZE