A team from the Institute of Chemistry won the prestigious Werner von Siemens Award for the best thesis
The Werner von Siemens Award for first place in the Best Diploma Thesis category went to Ing. Jiří Navrátil from the Faculty of Technology of the Tomas Bata University in Zlín for his diploma thesis entitled Synthesis of a ligand based on 4,9-disubstituted diamantane and study of its supramolecular properties. Jiří Navrátil\'s work deals with the study of the formation of supramolecular complexes of the host-guest type, where macrocyclic compounds from the cyclodextrin and cucurbit[n]uril families act as host molecules, and a ligand based on axially disubstituted diamantane acts as guest molecules. The aim of the work was to prepare the relevant ligand and subsequently investigate its supramolecular behaviour in detail. The results obtained were surprising and very interesting: this is the first dicationic ligand based on diamantane forming very stable host-guest complexes with macrocycles from the cyclodextrin family and at the same time the first work describing the ability of the diamantane cage to form supramolecular complexes with more than one (same or different) macrocyclic compound at a given time. A compound that took three years to appear Diamantanoids do not have the word \"diamond\" in their name by chance. In general, their structures can be derived from the basic building blocks of diamond - a well-known mineral composed only of carbon atoms. The smallest of the diamantanoids is adamantane, a tricyclic hydrocarbon isolated in the 1930s by Stanislav Landa from Hodonín oil. “We have been studying the chemistry of adamantane in our research group for more than 20 years,” says the thesis leader Michal Rouchal, adding: “The second in line is diamantane, which differs from adamantane not only in its size but also in the possibility of axial disubstitution (both substituents in one straight line), which seemed very interesting and advantageous from the point of view of designing new binding motifs for supramolecular host-guest systems. That is why we decided to write a thesis on this topic.” “The idea that my task would be to synthesize a molecule with a previously undescribed structure, and if I was successful, I would be able to study its supramolecular behaviour, immediately interested me. The fact that I would be the first to prepare this substance probably fascinated me the most. That is why I eagerly threw myself into work in the summer between my first and second year, thus beginning my almost three-year journey towards the desired ligand,” recalls Jiří Navrátil. The path to the goal was not easy. Jiří held the first tens of milligrams of the dream ligand in his hand only after three years of “synthetic toil”, when in some cases it was necessary to carefully optimize the reaction conditions. Patience and effort paid off in the end. The new diamantane ligand surprised everyone with its unexpected properties. “Jirka’s results are not only very interesting but above all valuable. In particular, the ability of the ligand to bind multiple macrocycles closely placed in one binding site, and probably in different mutual orientations, brings a lot of new things to the world of host-guest chemistry and opens doors that were previously closed or only partially open,” adds Michal Rouchal. Submitting the application was a good decision. A good topic, with very interesting results, and an above-average quality manuscript. According to Michal Rouchal, this is exactly what they said about applying for the Werner von Siemens Prize. Jiří was motivated to find out how his thesis would fare in the huge competition that prevails in the competition every year. That it would ultimately result in the first place, but neither of them had imagined it. Jiří and Michal value the award very much, but at the same time they add that it is a success of the entire supramolecular chemistry team led by Robert Vícha, and in a broader context of the Faculty of Technology and Tomas Bata University in Zlín. Here you can watch the YouTube medallion: Synthesis of a ligand based on 4,9-disubstituted diamantane and study of its supramolecular properties.
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