The Biomimetic Synthesis of Polyarylated Fluorenes, Relevant to Selaginellaceae Polyphenols, Leading to the Spontaneous Formation of Stable Radicals

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dc.authorid0000-0002-1740-4867en_US
dc.authorscopusid22136607900en_US
dc.authorwosid-en_US
dc.contributor.authorNallappan, Sundaravelu
dc.contributor.authorLapinskaite, Ringaile
dc.contributor.authorHajicek, Josef
dc.contributor.authorKunak, Dominik
dc.contributor.authorCambal, Peter
dc.contributor.authorB. Tümer, Tuğba
dc.date.accessioned2024-02-07T05:41:33Z
dc.date.available2024-02-07T05:41:33Z
dc.date.issued2023en_US
dc.departmentFakülteler, Fen Fakültesi, Moleküler Biyoloji ve Genetik Bölümü
dc.description.abstractThis work reports a biomimetic synthesis of polyarylated fluorene derivatives. The molecules are formed via intramolecular electrophilic aromatic substitution, resembling a cyclization leading towards the natural selaginpulvilins from selaginellins. The scope of the reaction was investigated, and the products were obtained in 60–95 % yields. Some of the compounds decompose to a stable radical. We investigated the nature and the origin of the radical using experimental methods, including EPR or electrochemical measurements, as well as theoretical methods, such as DFT calculations. Based on our observations, we hypothesize, that phenoxy radicals are formed in the first instance, which however undergo internal rearrangement to thermodynamically more stable carbon-centered radicals. The preliminary data also show the cytotoxic properties of some of the molecules.en_US
dc.identifier.citationNallappan, S., Lapinskaite, R., Hájíček, J., Kunák, D., Čambal, P., Nečas, D., … Rycek, L. (2023). The Biomimetic Synthesis of Polyarylated Fluorenes, Relevant to Selaginellaceae Polyphenols, Leading to the Spontaneous Formation of Stable Radicals. ChemPlusChem. https://doi.org/10.1002/cplu.202300410en_US
dc.identifier.doi10.1002/cplu.202300410
dc.identifier.issn2192-6506
dc.identifier.pmid37943550
dc.identifier.scopus2-s2.0-85177886399
dc.identifier.urihttps://doi.org/10.1002/cplu.202300410
dc.identifier.urihttps://hdl.handle.net/20.500.12428/5540
dc.identifier.wosWOS:001110088900001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.institutionauthorBoyuneğmez Tümer, Tuğba
dc.language.isoen
dc.publisherJohn Wiley and Sons Incen_US
dc.relation.ispartofChemPlusChemen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.rightsAttribution 3.0 United States*
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/us/*
dc.subjectBiomimetic synthesisen_US
dc.subjectCytotoxicityen_US
dc.subjectRadicalsen_US
dc.subjectSelaginellacea polyphenolsen_US
dc.subjectSpin density distributionen_US
dc.titleThe Biomimetic Synthesis of Polyarylated Fluorenes, Relevant to Selaginellaceae Polyphenols, Leading to the Spontaneous Formation of Stable Radicals
dc.typeArticle

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