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 editorsKiesilä, Anniina; Beyeh, Ngong Kodiah; Moilanen, Jani O.; Puttreddy, Rakesh; Götz, Sven; Rissanen, Kari; Barran, Perdita; Lützen, Arne; Kalenius, Elina

Journal or seriesOrganic and Biomolecular Chemistry

ISSN1477-0520

eISSN1477-0539

Publication year2019

Volume17

Issue number29

Pages range6980-6984

PublisherRoyal Society of Chemistry

Publication countryUnited Kingdom

Publication languageEnglish

DOIhttps://doi.org/10.1039/C9OB01383K

Publication open accessOpenly available

Publication channel open accessPartially 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.


Keywordssupramolecular chemistryhydrogen bonds


Contributing organizations


Related projects


Ministry reportingYes

Reporting Year2019

JUFO rating1


Last updated on 2024-11-05 at 22:05