Supramolecular chemistry of anion-binding receptors based on concave macrocycles
This thesis describes the supramolecular chemistry of different anion-binding
host molecules with a special focus on pyridine[4]arenes. The first part of the
thesis gives a brief introduction to supramolecular chemistry and its special
features, host-guest chemistry and self-assembly. Later on, a short review of
different hosts is presented, especially focusing on those utilized in the
experimental part of the thesis. In the second part of the thesis an introduction is
presented to the structural analyzation techniques utilized in the experimental
part. A special focus is set on ion mobility mass spectrometry, a relatively new
technique for structural characterization of supramolecular complexes.
The third part presents the summary of experimental work. The binding
properties of pyridinearene turned out to completely differ from previous reports
in the literature. New binding features of pyridinearene were discovered,
such as simultaneous endo- and exo-complex formation with neutral and anionic
guests. The formation of the hexameric assembly of pyridinearene was also observed
for the first time in gas phase and in solid state. In solution, the thermodynamic
balance in self-assembly was revealed.
Different analyzation techniques have been utilized in the structural characterisation
of pyridinearenes. Ion mobility mass spectrometry proved to be
spectacular for structural characterization of the gas phase assemblies. As a new
technique, its utilization for structural chemistry is demonstrated in the experimental
part with several examples.
In this thesis, also the binding properties of cyclohexylhemicucurbit[8]uril
and crown ether urea receptors were revealed and thoroughly studied in gas
phase, solution and in solid state.
Keywords: pyridine[4]arene, supramolecular chemistry, ion mobility mass
spectrometry, self-assembly, anion binding, X-ray crystallography
...


ISBN
978-951-39-7855-6ISSN Search the Publication Forum
2489-9003Contains publications
- Artikkeli I: Kiesilä, A., Kivijärvi, L., Beyeh, N. K., Moilanen, J., Groessl, M., Rothe, T., . . . Kalenius, E. (2017). Simultaneous Endo- and Exo-Complex Formation of Pyridine[4]arene Dimer with Neutral and Anionic Guests. Angewandte Chemie International Edition, 56 (36), 10942-10946. DOI: 10.1002/anie.201704054
- Artikkeli II: Kiesilä, Anniina; Moilanen, Jani O.; Kruve, Anneli.; Schalley, Christoph A.; Barran, Perdita; Kalenius, Elina (2019). Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers. Beilstein Journal of Organic Chemistry, 15, 2486–2492. DOI: 10.3762/bjoc.15.241
- Artikkeli III: Kiesilä, Anniina; Beyeh, Ngong Kodiah; Moilanen, Jani O.; Puttreddy, Rakesh; Götz, Sven; Rissanen, Kari; Barran, Perdita; Lützen, Arne; Kalenius, Elina (2019). Thermodynamically driven self-assembly of pyridinearene to hexameric capsules. Organic and Biomolecular Chemistry, 17 (29), 6980-6984. DOI: 10.1039/C9OB01383K
- Artikkeli IV: Kaabel, S., Adamson, J., Topic, F., Kiesilä, A., Kalenius, E., Öeren, M., . . . Aav, R. (2017). Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution. Chemical Science, 8 (3), 2184-2190. DOI: 10.1039/C6SC05058A
- Artikkeli V: Mäkelä, T., Kiesilä, A., Kalenius, E., & Rissanen, K. (2016). Ion-Pair Complexation with Dibenzo[21]Crown-7 and Dibenzo[24]Crown-8 bis-Urea Receptors. Chemistry: A European Journal, 22 (40), 14264-14272. DOI: 10.1002/chem.201602362
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- JYU Dissertations [694]
- Väitöskirjat [3299]
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