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Diamondoid scaffolds containing heteroatoms – preparation and application in development of advanced materials

Category
Projekti Hrvatske zaklade za znanost
Total cost
1225000
HRK
Start date
Sep 1st 2018
End date
Aug 31st 2023
Status
Done
More information

Principal investigator

Development of new materials is an important key topic in chemistry and cutting edge research is devoted to discover, improve and apply them in future technologies. Currently special focus is placed on carbon-based materials, with diamond being a highly attractive scaffold. Despite its numerous excellent properties, diamond is still difficult to control in terms of selective functionalization and material uniformity. An alternative to bulk diamond are diamondoids, organic cage compounds that have a diamond-like structure but can be selectively substituted, thereby bridging the gap between flexible organic molecules and bulk diamond.

Chemistry of diamondoids saw a breakthrough in the last two decades but there are still opportunities for further development. Our goal is to prepare and characterize unexplored diamondoid derivatives and apply them in materials design. Target compounds will be diamondoid scaffolds selectively functionalized with heteroatoms bound on the cage itself as well as derivatives with spacers, including ethers, thioethers, amines (secondary and higher), esters, etc. To achieve this, we will go beyond the state-of-the-art and develop new strategies for their selective functionalization and polyfunctionalization, since precise diamondoid substitution enables properties control. The next step will be tailoring of properties by introduction of secondary motifs/functionalities on the prepared diamondoid scaffolds, with a goal to pave the way for future application in coatings and advanced surfaces. Experimental studies will be complemented by computational methods to gain more insight into the physico-chemical nature of both the molecules and the materials they will form. The proposed research will therefore deepen the fundamental knowledge of structure-properties relationship in the design of new candidates for advanced materials, with a focus on highly promising carbon-based organic scaffolds.

Publications

11. J. Alić, I. Lončarić, M. Etter, M. Rubčić, Z. Štefanić, M. Šekutor, K. Užarević, T. Stolar, Direct in situ measurement of polymorphic transition temperatures under thermo-mechanochemical conditions, Phys. Chem. Chem. Phys. 2024, 26, 4840–4844.

10. M. Alešković, M. Šekutor, Overcoming barriers with non-covalent interactions: Supramolecular recognition of adamantyl cucurbit[n]uril assemblies for medical applications, RSC Med. Chem. 2024, DOI: 10.1039/D3MD00596H => review

9. 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. J. Chem. 2023, 47, 18745–18755.

8. P. Pinacho, D. Loru, T. Šumanovac, M. Šekutor, M. Schnell, Increasing complexity in adamantyl thioethers characterized by rotational spectroscopy, ChemPhysChem 2023, 24, e2023005. => Editors' Choice: Spotlights, Cover Feature

7. M. Alešković, F. Küstner, R. Messner, F. Lackner, W. E. Ernst, M. Šekutor, Nanostructured supramolecular networks from self-assembled diamondoid molecules at ultracold conditions, Phys. Chem. Chem. Phys. 2023, 25, 17869–17876. => 2023 PCCP HOT Article

6. J. Alić, R. Messner, M. Alešković, F. Küstner, M. Rubčić, F. Lackner, W. E. Ernst, M. Šekutor, Diamondoid ether clusters in helium nanodroplets, Phys. Chem. Chem. Phys. 2023, 25, 11951–11958. => cover

5. D. King, T. Šumanovac, S. Murkli, P. R. Schreiner, M. Šekutor, L. Isaacs, Cucurbit[8]uril Forms Tight Inclusion Complexes with Cationic Triamantanes, New J. Chem. 2023, 47, 5338–5346.

4. J. Alić, T. Stolar, Z. Štefanić, K. Užarević, M. Šekutor, Sustainable Synthesis of Diamondoid Ethers by High-Temperature Ball Milling, ACS Sustainable Chem. Eng. 2023, 11, 617–624.

3. M. Alešković, S. Roca, R. Jozepović, N. Bregović, M. Šekutor, Unravelling Binding Effects in Cyclodextrin Inclusion Complexes with Diamondoid Ammonium Salt GuestsNew. J. Chem. 2022, 46, 13406–13414. => front cover

2. J. Alić, I. Biljan, Z. Štefanić, M. Šekutor, Preparation and characterization of non-aromatic ether self-assemblies on a HOPG surfaceNanotechnology 2022, 33, 355603.

1. J. Alić, R. Messner, F. Lackner, W. E. Ernst, M. Šekutor, London dispersion dominating diamantane packing in helium nanodropletsPhys. Chem. Chem. Phys. 2021, 23, 21833–21839.

Dissemination

42. M. Šekutor, Design and characterization of diamondoid on-surface assemblies, Invited Seminar at the Institute of Experimental Physics, Graz University of Technology, October 5, 2023, Graz, Austria. => lecture

41. M. Šekutor, Characterization of Diamondoid Clusters Emerging in Helium Nanodroplets, Computational Chemistry Day 2023, September 16, 2023, Zagreb, Croatia, CL 7, 17. => lecture

40. J. Alić, I. Biljan, Z. Štefanić, M. Šekutor, Characterization of diamondoid ether self-assemblies on a HOPG surface, 7th Adriatic NMR, June 1–4, 2023, Mali Ston, Croatia, P07, 53. => poster

39. J. Požar, A. Usenik, M. Alešković, S. Roca, I. Markuš, M. Šekutor, Comparative study of cyclodextrin binding affinities for diamondoid alcohols, 7th Adriatic NMR, June 1–4, 2023, Mali Ston, Croatia, P03, 49. => poster

38. M. Alešković, S. Roca, A. Ernečić, N. Bregović, M. Šekutor, NMR insights into diamondoid ammonium salt inclusion complexes with cyclodextrins, 7th Adriatic NMR, June 1–4, 2023, Mali Ston, Croatia, 37. => lecture

37. M. Šekutor, Design and characterization of diamondoid covalent assemblies, 7th Adriatic NMR, June 1–4, 2023, Mali Ston, Croatia, 28. => lecture

36. M. Šekutor, A Story of Diamondoids: From Supramolecular Assemblies to Nanotechnology, Invited Seminar at George Washington University, March 31, 2023, Washington D.C., USA.=> lecture

35. M. Šekutor, A Story of Diamondoids: From Supramolecular Assemblies to Nanotechnology, Invited Seminar at Georgetown University, March 30, 2023, Washington D.C., USA. => lecture

34. M. Šekutor, A Story of Diamondoids: From Supramolecular Assemblies to Nanotechnology, Invited Seminar at University of Maryland, March 27, 2023, College Park, Maryland, USA. => lecture

33. M. Šekutor, Diamantane self-assembly in helium nanodroplets, COSY COST Action CA21101, Working Group 3 Virtual Symposium, December 12, 2022, webinar, S2. => lecture

32. A. Ernečić, S. Roca, N. Bregović, V. Lazarenko, M. Šekutor, M. Alešković, A Supramolecular Study on Inclusion Complexes of Diamondoid Ammonium Salts with Cyclodextrins, Supramolecular Chemistry 2022 (SupramolChem2022), December 8, 2022, Zagreb, Croatia. => poster

31. N. Burić, M. Šekutor, Preparation and Mass Spectral Characterization of Diamondoid Derivatives, Solutions in Chemistry 2022, November 8–11, 2022, Sveti Martin na Muri, Croatia, P8, 86. => poster

30. J. Alić Stolar, T. Stolar, Z. Štefanić, K. Užarević, M. Šekutor, Sustainable Solution for Synthesis of Diamondoid Ethers, Solutions in Chemistry 2022, November 8–11, 2022, Sveti Martin na Muri, Croatia, P3, 81. => poster

29. M. Alešković, A. Ernečić, S. Roca, V. Lazarenko, N. Bregović, M. Šekutor, Structural and Thermodynamic Features of Diamondoid Ammonium Salt Inclusion Complexes with Cyclodextrins, Solutions in Chemistry 2022, November 8–11, 2022, Sveti Martin na Muri, Croatia, P2, 80. => poster

28. A. Ernečić, S. Roca, N. Bregović, V. Lazarenko, M. Šekutor, M. Alešković, Investigation of Inclusion Complexes of Diamondoid Ammonium Salts with Cyclodextrins, 7th Faculty of Science PhD Student Symposium, University of Zagreb, October 22, 2022, Zagreb, Croatia, P21, 67. => poster

27. J. Alić, I. Biljan, Z. Štefanić, M. Šekutor, Characterization of Diamondoid Ether Self-Assemblies on a HOPG Surface, Computational Chemistry Day 2022, September 24, 2022, Zagreb, Croatia, P3, 21. => poster

26. J. Alić, T. Stolar, Z. Štefanić, K. Užarević, M. Šekutor, Sustainable mechanochemical synthesis of diamondoid ethers, 25th International Conference on the Chemistry of the Organic Solid State (ICCOSS XXV), July 3–8, 2022, Ohrid, Macedonia. => poster

25. S. Roca, A. Ernečić, N. Višić, M. Alešković, N. Bregović, M. Šekutor, Exploring Structural and Thermodynamic Properties of Various Diamantane Amine–Cyclodextrin Complexes, Magnetic Moments in Central Europe 2022 (MMCE 2022), Adriatic NMR, June 1–4, 2022, Primošten, Croatia, P37, 110. => poster

24. A. Ernečić, M. Alešković, S. Roca, N. Bregović, M. Šekutor, Adamantane Ammonium Salts as Guests for the Cyclodextrin Host: Something Old, Something New, Magnetic Moments in Central Europe 2022 (MMCE 2022), Adriatic NMR, June 1–4, 2022, Primošten, Croatia, P08, 81. => poster

23. I. Markuš, A. Usenik, M. Alešković, M. Šekutor, J. Požar, Hydrophobic cavities and diamantanes, XIV Meeting of Young Chemical Engineers, February 24–25, 2022, Zagreb, Croatia, 81. => poster

22. M. Šekutor, Diamondoids in supramolecular chemistry and chemistry of materijals, 27. Lecture of the Division of Organic Chemistry and Biochemistry of the Ruđer Bošković Institute and the Section for Organic Chemistry of the Croatian Chemical Society, February 8, 2022, Zagreb, Croatia. => lecture

21. I. Markuš, A. Usenik, K. Pičuljan, M. Alešković, M. Šekutor, J. Požar, Diamantane Alcohols and Hydrophobic Cavities: The (not so) Perfect Match in Water and Structured Organic Solvents, Supramolecular Chemistry 2021 (SupramolChem2021), December 10, 2021, Zagreb, Croatia. => poster

20. M. Alešković, S. Roca, N. Bregović, M. Šekutor, Supramolecular Chemistry of Diamondoid Ammonium Salts, Supramolecular Chemistry 2021 (SupramolChem2021), December 10, 2021, Zagreb, Croatia. => lecture

19. I. Markuš, A. Usenik, K. Pičuljan, M. Alešković, M. Šekutor, J. Požar, Diamantane alcohols and hydrophobic cavities: The prefect pair also in non-aqueous solution? 27th Croatian Meeting of Chemists and Chemical Engineers and the 5th "Vladimir Prelog" Symposium, October 5–8, 2021, Veli Lošinj, Croatia. => poster

18. Z. Jurić, A. Mandić, T. Šumanovac, M. Šekutor, Đ. Škalamera, Preparation and conformational analysis of 1,1'-biadamantane and its derivatives, 27th Croatian Meeting of Chemists and Chemical Engineers and the 5th "Vladimir Prelog" Symposium, October 5–8, 2021, Veli Lošinj, Croatia. => poster

17. M. Šekutor, J. Alić, R. Messner, F. Lackner, W. E. Ernst, The role of London dispersion in the formation of diamantane clusters inside helium nanodroplets, 27th Croatian Meeting of Chemists and Chemical Engineers and the 5th "Vladimir Prelog" Symposium, October 5–8, 2021, Veli Lošinj, Croatia. => lecture

16. N. Burić, M. Šekutor, Preparation and characterization of diamondoid esters, 27th Croatian Meeting of Chemists and Chemical Engineers and the 5th "Vladimir Prelog" Symposium, October 5–8, 2021, Veli Lošinj, Croatia. => lecture

15. A. Usenik, I. Markuš, K. Pičuljan, M. Alešković, M. Šekutor, J. Požar, Diamantanes are a Hydrophobic Cavity's Best Friend: the Role of Solvent Structuring in Complex Stability, Adriatic NMR Conference 2021, September 13–15, 2021, Primošten, Croatia, P13, 61. => poster

14. J. Alić, I. Biljan, Z. Štefanić, M. Šekutor, Self-assembly of diamondoid ethers on graphite, Solid-State Science & Research (SCIRES2021), Ruđer Bošković Institute, Zagreb, June 10–11, 2021, videoconference => poster (poster award)

13. N. Burić, M. Šekutor, Synthesis of diamondoid esters for supramolecular self-assembly, 5th Faculty of Science PhD Student Symposium, University of Zagreb, April 24–25, 2021, Zagreb, Croatia, M-K4, 158. => lecture + poster

12. M. Alešković, R. Jozepović, S. Roca, N. Bregović, M. Šekutor, Synthesis and Binding of Permethylated Diamondoid Ammonium Salts, Adriatic NMR Conference 2020, September 22–24, 2020, Peroj, Croatia, P1, 37. => poster

11. N. Burić, M. Šekutor, Diamondoid esters in nanomaterial design, 18th Ružička Days “Today Science – Tomorrow Industry", September 16–18, 2020, Vukovar, Croatia, 24. => poster

10. J. Alić, M. Šekutor, Characterization of diamantane clusters in helium nanodroplets, Symposium of doctoral students of the Faculty of Science 2020, University of Zagreb, February 28, 2020, Zagreb, Croatia, U-K2, 32. => lecture

9. M. Šekutor, Young women researchers in STEM: the present and outlook for the future, Gender 4 STEM conference – Gender aware education and teaching, Ruđer Bošković Institute, February 6, 2020, Zagreb, Croatia. => lecture

8. M. Šekutor, N. Burić, J. Alić, Chemistry and application of diamondoid derivatives, 15th EYCN Delegate Assembly, January 26–29, 2020, Sitges, Spain, P9. => poster

7. M. Šekutor, Young scientists in the next decade: education and chances, Roundtable II, Science and educational challenges facing Europe in the next decade, Humboldt College Zagreb, October 10–11, 2019, Zagreb, Croatia. => round table

6. J. Alić, N. Burić, M. Šekutor, Diamondoids in supramolecular chemistry and nanotechnology, Science and educational challenges facing Europe in the next decade, Humboldt College Zagreb, October 10–11, 2019, Zagreb, Croatia, 24. => poster

5. M. Šekutor, Diamondoids as scaffolds in supramolecular chemistry and nanomaterials, 1st Joint Croatian - Chinese Mini Symposium on Chemistry, Institut Ruđer Bošković, September 3, 2019, Zagreb, Croatia. => lecture

4. M. Šekutor, The Role of London Dispersion in Structural Organization of Polycyclic Cage Compounds, Young Investigator Workshop 2019 EuChemS, July 11–13, 2019, Vienna, Austria. => lecture

3. M. Šekutor, Potential Bioapplication of Adamantyl Aminoguanidines, Scientific Seminar at Fidelta d.o.o., May 20, 2019, Zagreb, Croatia. => lecture

2. M. Šekutor, Configuration and reactivity of diamondoids on a Cu(111) surface, Computational Chemistry Day 2019, May 11, 2019, Zagreb, Croatia, L2. => lecture

1. M. Šekutor, On-surface Orientation and Reactivity of Diamondoid Compounds, 26th Croatian Meeting of Chemists and Chemical Engineers and the 4th "Vladimir Prelog" Symposium, April 9–12, 2019, Šibenik, Croatia, 22. => lecture

Associates

dr. sc. Marija Alešković

dr. sc. Margareta Sohora

Nataša Burić, dipl. ing.

Funding

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