Thermodynamically driven self-assembly of pyridinearene to hexameric capsules
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
Julkaistu sarjassa
Organic and Biomolecular ChemistryTekijät
Päivämäärä
2019Tekijänoikeudet
© The Royal Society of Chemistry, 2019
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.
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Julkaisija
Royal Society of ChemistryISSN Hae Julkaisufoorumista
1477-0520Asiasanat
Julkaisu tutkimustietojärjestelmässä
https://converis.jyu.fi/converis/portal/detail/Publication/32150932
Metadata
Näytä kaikki kuvailutiedotKokoelmat
Rahoittaja(t)
Suomen AkatemiaRahoitusohjelmat(t)
Akatemiatutkijan tutkimuskulut, SA; Akatemiatutkija, SA; Tutkijatohtori, SALisätietoja rahoituksesta
The authors acknowledge the Academy of Finland for the funding (JOM: 285855, 315829, 320015, RP: 298817, EK: 284562, 278743 and 312514) as well as Prof. H. M. Tuononen, University of Jyväskylä, CSC-IT Center for Science in Finland, and the Finnish Grid and Cloud Infrastructure (persistent identifierurn:nbn:fi:research-infras-2016072533) for providing computational resources. NKB gratefully acknowledge the financial support from Oakland University, MI, USA. ...Lisenssi
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