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para–phenylenediamine dimer as a redox–active guest for supramolecular systems

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dc.title para–phenylenediamine dimer as a redox–active guest for supramolecular systems en
dc.contributor.author Janovský, Petr
dc.contributor.author Springer, Andreas
dc.contributor.author Filip, Jaroslav
dc.contributor.author Prucková, Zdeňka
dc.contributor.author Nečas, Marek
dc.contributor.author Rouchal, Michal
dc.contributor.author Schalley, Christoph A.
dc.contributor.author Vícha, Robert
dc.relation.ispartof Chemistry - A European Journal
dc.identifier.issn 0947-6539 Scopus Sources, Sherpa/RoMEO, JCR
dc.identifier.issn 1521-3765 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2024
dc.type article
dc.language.iso en
dc.publisher Wiley
dc.identifier.doi 10.1002/chem.202400535
dc.relation.uri https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202400535
dc.relation.uri https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/chem.202400535
dc.subject cucurbiturils en
dc.subject cyclodextrins en
dc.subject host–guest systems en
dc.subject redox-active dye en
dc.description.abstract Redox–active components are highly valuable in the construction of molecular devices. We combined two p-phenylenediamines (p-PDA) with a biphenyl (BiPhe) unit to prepare a supramolecular guest 4 consisting of three binding sites for cucurbit[7/8]uril (CBn) and/or cyclodextrins (CD). Supramolecular properties of 4 were investigated using NMR, UV-vis, mass spectrometry and isothermal titration calorimetry. Our analysis revealed that 4 forms higher–order host–guest complexes, wherein a CD unit occupies the central BiPhe site, secured by two CBn units at the terminal p-PDA sites. Additionally, 1 : 1 complexes with α-CD and β-CD, a 1 : 2 complex with γ-CD and 2 : 1 complexes with CB7 and CB8 were identified. Through UV-vis and cyclic voltammetry, redox processes leading to the formation of a stable, deep blue dication diradical of 4 are elucidated. Furthermore, it is demonstrated that CB7 selectively protects oxidised 4 from reduction in the presence of a reducing agent. The supramolecular and redox properties of the structural motif represented by 4 render it an interesting candidate for the construction of supramolecular devices. en
utb.faculty Faculty of Technology
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1011962
utb.identifier.scopus 2-s2.0-85188232192
utb.identifier.wok 001188552000001
utb.identifier.pubmed 38415892
utb.identifier.coden CEUJE
utb.source j-scopus
dc.date.accessioned 2024-04-17T13:13:04Z
dc.date.available 2024-04-17T13:13:04Z
dc.description.sponsorship Internal Funding Agency of TBU in Zlin [IGA/FT/2023/001]; Deutsche Forschungsgemeinschaft - MEYS CR [LM2023042]
dc.rights Attribution-NonCommercial 4.0 International
dc.rights.uri http://creativecommons.org/licenses/by-nc/4.0/
dc.rights.access openAccess
utb.ou Department of Chemistry
utb.ou Department of Environmental Protection Engineering
utb.contributor.internalauthor Janovský, Petr
utb.contributor.internalauthor Filip, Jaroslav
utb.contributor.internalauthor Prucková, Zdeňka
utb.contributor.internalauthor Rouchal, Michal
utb.contributor.internalauthor Vícha, Robert
utb.fulltext.affiliation Petr Janovský a, Andreas Springer b, Jaroslav Filip c, Zdeňka Prucková a, Marek Nečas d, Michal Rouchal a, Christoph A. Schalley b, Dr. Robert Vícha a a Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 5669, 760 01 Zlín, Czech Republic b Institut für Chemie und Biochemie, Freie Universität Berlin, Arnimallee 20, 14195 Berlin, German c Department of Environmental Protection Engineering, Faculty of Technology, Tomas Bata University in Zlín, Nad Ovčírnou, 3685, 760 01 Zlín, Czech Republic d Department of Chemistry, Faculty of Science, Masaryk University, Kotlářská 2, 602 00 Brno, Czech Republic
utb.fulltext.dates Issue Online: 02 May 2024 Version of Record online: 21 March 2024 Accepted manuscript online: 28 February 2024 Manuscript received: 06 February 2024
utb.fulltext.sponsorship The work was supported by the Internal Funding Agency of TBU in Zlín (project number IGA/FT/2023/001). We acknowledge the assistance of the Core Facility BioSupraMol supported by the Deutsche Forschungsgemeinschaft and the X-ray Diffraction and Bio-SAXS Core Facility of CIISB, Instruct-CZ Centre, supported by MEYS CR (LM2023042). Open Access publishing facilitated by Univerzita Tomase Bati ve Zline, as part of the Wiley - CzechELib agreement.
utb.wos.affiliation [Janovsky, Petr; Pruckova, Zdenka; Rouchal, Michal; Vicha, Robert] Tomas Bata Univ Zlin, Fac Technol, Dept Chem, Vavreckova 5669, Zlin 76001, Czech Republic; [Springer, Andreas; Schalley, Christoph A.] Freien Univ Berlin, Inst Chem & Biochem, Arnimallee 20, D-14195 Berlin, Germany; [Filip, Jaroslav] Tomas Bata Univ Zlin, Fac Technol, Dept Environm Protect Engn, Ovcirnou 3685, Zlin 76001, Czech Republic; [Necas, Marek] Masaryk Univ, Fac Sci, Dept Chem, Kotlarska 2, Brno 60200, Czech Republic
utb.scopus.affiliation Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 5669, Zlín, 760 01, Czech Republic; Institut für Chemie und Biochemie, Freie Universität Berlin, Arnimallee 20, Berlin, 14195, Germany; Department of Environmental Protection Engineering, Faculty of Technology, Tomas Bata University in Zlín, Nad Ovčírnou, 3685, Zlín, 760 01, Czech Republic; Department of Chemistry, Faculty of Science, Masaryk University, Kotlářská 2, Brno, 602 00, Czech Republic
utb.fulltext.projects IGA/FT/2023/001
utb.fulltext.projects LM2023042
utb.fulltext.faculty Faculty of Technology
utb.fulltext.faculty Faculty of Technology
utb.fulltext.ou Department of Chemistry
utb.fulltext.ou Department of Environmental Protection Engineering
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