A1 Journal article (refereed)
Thermodynamically driven self-assembly of pyridinearene to hexameric capsules (2019)
Kiesilä, A., Beyeh, N. K., Moilanen, J. O., Puttreddy, R., Götz, S., Rissanen, K., Barran, P., Lützen, A., & Kalenius, E. (2019). Thermodynamically driven self-assembly of pyridinearene to hexameric capsules. Organic and Biomolecular Chemistry, 17(29), 6980-6984. https://doi.org/10.1039/C9OB01383K
JYU authors or editors
Publication details
All authors or editors: Kiesilä, Anniina; Beyeh, Ngong Kodiah; Moilanen, Jani O.; Puttreddy, Rakesh; Götz, Sven; Rissanen, Kari; Barran, Perdita; Lützen, Arne; Kalenius, Elina
Journal or series: Organic and Biomolecular Chemistry
ISSN: 1477-0520
eISSN: 1477-0539
Publication year: 2019
Volume: 17
Issue number: 29
Pages range: 6980-6984
Publisher: Royal Society of Chemistry
Publication country: United Kingdom
Publication language: English
DOI: https://doi.org/10.1039/C9OB01383K
Publication open access: Openly available
Publication channel open access: Partially open access channel
Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/65411
Abstract
Pyridinearene macrocycles have previously shown unique host–guest properties in their capsular dimers including endo complexation of neutral molecules and exo complexation of anions. Here, we demonstrate for the first time the formation of hydrogen bonded hexamer of tetraisobutyl-octahydroxypyridinearene in all three states of matter – gas phase, solution and solid-state. Cationic tris(bipyridine)ruthenium(II) template was found to stabilize the hexamer in gas phase, whereas solvent molecules do this in condensed phases. In solution, the capsular hexamer was found to be the thermodynamically favoured self-assembly product and transition from dimer to hexamer occurred in course of time. The crystal structure of hexamer revealed 24 N–H⋯O direct intermolecular hydrogen bonds between the six pyridinearene macrocycles without any bridging solvent molecules. Hydrogen bond patterns correlate well with DFT computed structures. Thus, all structural chemistry methods (IM-MS, DOSY NMR, DFT, X-ray crystallography) support the same structure of the hexameric capsule that has a diameter of ca. 3 nm and volume of 1160 Å3.
Keywords: supramolecular chemistry; hydrogen bonds
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Ministry reporting: Yes
Reporting Year: 2019
JUFO rating: 1