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Cooperative Binding of Cucurbit[n]urils and β-Cyclodextrin to Heteroditopic Imidazolium-Based Guests

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dc.title Cooperative Binding of Cucurbit[n]urils and β-Cyclodextrin to Heteroditopic Imidazolium-Based Guests en
dc.contributor.author Branná, Petra
dc.contributor.author Černochová, Jarmila
dc.contributor.author Rouchal, Michal
dc.contributor.author Kulhánek, Petr
dc.contributor.author Babinský, Martin
dc.contributor.author Marek, Radek
dc.contributor.author Nečas, Marek
dc.contributor.author Kuřitka, Ivo
dc.contributor.author Vícha, Robert
dc.relation.ispartof Journal of Organic Chemistry
dc.identifier.issn 0022-3263 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2016
utb.relation.volume 81
utb.relation.issue 20
dc.citation.spage 9595
dc.citation.epage 9604
dc.type article
dc.language.iso en
dc.publisher American Chemical Society (ACS)
dc.identifier.doi 10.1021/acs.joc.6b01564
dc.relation.uri http://pubs.acs.org/doi/full/10.1021/acs.joc.6b01564
dc.description.abstract Imidazolium-based guests containing two distinct binding epitopes are capable of binding beta-cyclodextrin and cucurbit[6/7]uril (CB) simultaneously to form heteroternary 1:1:1 inclusion complexes. In the final the hosts occupy binding sites disfavored in the binary complexes because of the chemically induced reorganization of the intermediate 1:1 aggregate. In addition, the reported guests are capable of binding two CBs to form either 1:2 or 1:1:1 ternary assemblies despite consisting of a single cationic moiety. Whereas the adamantane site binds CB solely via hydrophobic interactions, the CB unit at the butyl site is stabilized by a combination of hydrophobic and ion-dipole interactions. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1006853
utb.identifier.obdid 43875559
utb.identifier.scopus 2-s2.0-84992348961
utb.identifier.wok 000386187500009
utb.identifier.coden JOCEA
utb.source j-wok
dc.date.accessioned 2017-02-28T15:11:34Z
dc.date.available 2017-02-28T15:11:34Z
dc.description.sponsorship Internal Funding Agency of Tomas Bata University in Zlin [IGA/FT/2016/001]; Czech Science Foundation [16-05961S]; Ministry of Education, Youth and Sports of the Czech Republic under Project CEITEC [LQ1601]; CERIT Scientific Cloud under the program "Projects of Large Research, Development, and Innovations Infrastructures" [LM2015085]
utb.contributor.internalauthor Branná, Petra
utb.contributor.internalauthor Černochová, Jarmila
utb.contributor.internalauthor Rouchal, Michal
utb.contributor.internalauthor Kuřitka, Ivo
utb.contributor.internalauthor Vícha, Robert
utb.fulltext.affiliation Petra Branná , † Jarmila Černochová , †,‡ Michal Rouchal, † Petr Kulhánek, § Martin Babinský , § Radek Marek, §,∥ Marek Nečas, §,∥ Ivo Kuř itka, ‡ and Robert Vícha* ,† † Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavreč kova 275, 760 01 Zlín, Czech Republic Polymer Centre, Tomas Bata University in Zlín, Vavreč kova 275, 760 01 Zlín, Czech Republic § CEITEC-Central European Institute of Technology, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic ∥ Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
utb.fulltext.dates Received: June 29, 2016 Published: September 23, 2016
utb.fulltext.sponsorship This work was financially supported by the Internal Funding Agency of Tomas Bata University in Zlín (IGA/FT/2016/001 to P.B., M.R., and R.V.), by the Czech Science Foundation (16-05961S to R.M.), and by the Ministry of Education, Youth and Sports of the Czech Republic under Project CEITEC 2020 (LQ1601 to P.K.). Computational resources were provided by the CESNET LM2015042 and the CERIT Scientific Cloud LM2015085 under the program “Projects of Large Research, Development, and Innovations Infrastructures”.
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