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dc.contributor.authorKiesilä, Anniina
dc.contributor.authorBeyeh, Ngong Kodiah
dc.contributor.authorMoilanen, Jani O.
dc.contributor.authorPuttreddy, Rakesh
dc.contributor.authorGötz, Sven
dc.contributor.authorRissanen, Kari
dc.contributor.authorBarran, Perdita
dc.contributor.authorLützen, Arne
dc.contributor.authorKalenius, Elina
dc.date.accessioned2019-09-03T11:55:38Z
dc.date.available2019-09-03T11:55:38Z
dc.date.issued2019
dc.identifier.citationKiesilä, 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. <i>Organic and Biomolecular Chemistry</i>, <i>17</i>(29), 6980-6984. <a href="https://doi.org/10.1039/C9OB01383K" target="_blank">https://doi.org/10.1039/C9OB01383K</a>
dc.identifier.otherCONVID_32150932
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/65411
dc.description.abstractPyridinearene 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.en
dc.format.mimetypeapplication/pdf
dc.languageeng
dc.language.isoeng
dc.publisherRoyal Society of Chemistry
dc.relation.ispartofseriesOrganic and Biomolecular Chemistry
dc.rightsCC BY-NC 3.0
dc.titleThermodynamically driven self-assembly of pyridinearene to hexameric capsules
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-201909034017
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineNanoscience Centerfi
dc.contributor.oppiaineOrganic Chemistryen
dc.contributor.oppiaineNanoscience Centeren
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.description.reviewstatuspeerReviewed
dc.format.pagerange6980-6984
dc.relation.issn1477-0520
dc.relation.numberinseries29
dc.relation.volume17
dc.type.versionpublishedVersion
dc.rights.copyright© The Royal Society of Chemistry, 2019
dc.rights.accesslevelopenAccessfi
dc.relation.grantnumber284562
dc.relation.grantnumber278743
dc.relation.grantnumber298817
dc.relation.grantnumber285855
dc.relation.grantnumber320015
dc.relation.grantnumber315829
dc.relation.grantnumber312514
dc.subject.ysovetysidokset
dc.subject.ysosupramolekulaarinen kemia
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p38131
jyx.subject.urihttp://www.yso.fi/onto/yso/p37759
dc.rights.urlhttps://creativecommons.org/licenses/by-nc/3.0/
dc.relation.doi10.1039/C9OB01383K
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderAcademy of Finlanden
dc.relation.funderAcademy of Finlanden
dc.relation.funderAcademy of Finlanden
dc.relation.funderAcademy of Finlanden
dc.relation.funderAcademy of Finlanden
dc.relation.funderAcademy of Finlanden
dc.relation.funderAcademy of Finlanden
jyx.fundingprogramAkatemiatutkijan tutkimuskulut, SAfi
jyx.fundingprogramAkatemiatutkijan tehtävä, SAfi
jyx.fundingprogramTutkijatohtori, SAfi
jyx.fundingprogramTutkijatohtori, SAfi
jyx.fundingprogramAkatemiatutkijan tutkimuskulut, SAfi
jyx.fundingprogramAkatemiatutkijan tehtävä, SAfi
jyx.fundingprogramAkatemiatutkijan tutkimuskulut, SAfi
jyx.fundingprogramResearch costs of Academy Research Fellow, AoFen
jyx.fundingprogramResearch post as Academy Research Fellow, AoFen
jyx.fundingprogramPostdoctoral Researcher, AoFen
jyx.fundingprogramPostdoctoral Researcher, AoFen
jyx.fundingprogramResearch costs of Academy Research Fellow, AoFen
jyx.fundingprogramResearch post as Academy Research Fellow, AoFen
jyx.fundingprogramResearch costs of Academy Research Fellow, AoFen
jyx.fundinginformationThe 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.


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