Imidazo[1,5-a]pyridines – a versatile platform for structurally distinct N-heterocyclic olefins and π-extended heterocycles

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dc.contributor.authorEsken, Robin
dc.contributor.authorAntoni, Patrick W.
dc.contributor.authorLorenz, Yannick
dc.contributor.authorBurdenski, Chris
dc.contributor.authorKirchhoff, Jan-Lukas
dc.contributor.authorStrohmann, Carsten
dc.contributor.authorHansmann, Max M.
dc.date.accessioned2025-06-03T11:48:46Z
dc.date.available2025-06-03T11:48:46Z
dc.date.issued2025-04-17
dc.description.abstractThe synthesis of polarized N-heterocyclic olefins (NHOs) based on an imidazo[1,5-a]pyridine scaffold is presented. In contrast to regular NHOs the unique bicyclic heterocyclic core allows the incorporation of various substituents in close proximity to the highly polarized exocyclic C─C bond. The donor properties of the new carbon-based ligand class were quantified and the coordination chemistry explored. Alkenyl or alkynyl groups at the C5-position lead to spontaneous cyclization to yield imidazo[2,1,5-de]quinolizines. The unique cyclization strategy was compatible with a wide range of substitution patterns and yields highly electron-rich π-delocalized heterocycles. The electronic structure of the novel partially antiaromatic heterocycle was thoroughly investigated. One-electron oxidation occurs at low potentials and lead to a stable monomeric radical-cation confirmed by XRD, which showed solution phase fluorescence expanding into the field of open-shell organic materials.en
dc.identifier.urihttp://hdl.handle.net/2003/43718
dc.identifier.urihttp://dx.doi.org/10.17877/DE290R-25492
dc.language.isoen
dc.relation.ispartofseriesAngewandte Chemie. International edition
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectImidazo[2,1,5-de]quinolizinesen
dc.subjectDonor ligandsen
dc.subjectFluorescent organic radicalsen
dc.subjectN-heterocyclic olefinsen
dc.subjectParatropic ring currenten
dc.subject.ddc540
dc.titleImidazo[1,5-a]pyridines – a versatile platform for structurally distinct N-heterocyclic olefins and π-extended heterocyclesen
dc.typeText
dc.type.publicationtypeArticle
dcterms.accessRightsopen access
eldorado.openaire.projectidentifierinfo:eu-repo/grantAgreement/EC/HE/101077332/EU/NAME/CC-CHARGED
eldorado.secondarypublicationtrue
eldorado.secondarypublication.primarycitationR. Esken, P. W. Antoni, Y. Lorenz, C. Burdenski, J.-L. Kirchhoff, C. Strohmann, M. M. Hansmann, Angew. Chem. Int. Ed. 2025, e202506305. https://doi.org/10.1002/anie.202506305
eldorado.secondarypublication.primaryidentifierhttps://doi.org/10.1002/anie.202506305

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