Imidazo[1,5-a]pyridines – a versatile platform for structurally distinct N-heterocyclic olefins and π-extended heterocycles
dc.contributor.author | Esken, Robin | |
dc.contributor.author | Antoni, Patrick W. | |
dc.contributor.author | Lorenz, Yannick | |
dc.contributor.author | Burdenski, Chris | |
dc.contributor.author | Kirchhoff, Jan-Lukas | |
dc.contributor.author | Strohmann, Carsten | |
dc.contributor.author | Hansmann, Max M. | |
dc.date.accessioned | 2025-06-03T11:48:46Z | |
dc.date.available | 2025-06-03T11:48:46Z | |
dc.date.issued | 2025-04-17 | |
dc.description.abstract | The 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.uri | http://hdl.handle.net/2003/43718 | |
dc.identifier.uri | http://dx.doi.org/10.17877/DE290R-25492 | |
dc.language.iso | en | |
dc.relation.ispartofseries | Angewandte Chemie. International edition | |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | |
dc.subject | Imidazo[2,1,5-de]quinolizines | en |
dc.subject | Donor ligands | en |
dc.subject | Fluorescent organic radicals | en |
dc.subject | N-heterocyclic olefins | en |
dc.subject | Paratropic ring current | en |
dc.subject.ddc | 540 | |
dc.title | Imidazo[1,5-a]pyridines – a versatile platform for structurally distinct N-heterocyclic olefins and π-extended heterocycles | en |
dc.type | Text | |
dc.type.publicationtype | Article | |
dcterms.accessRights | open access | |
eldorado.openaire.projectidentifier | info:eu-repo/grantAgreement/EC/HE/101077332/EU/NAME/CC-CHARGED | |
eldorado.secondarypublication | true | |
eldorado.secondarypublication.primarycitation | R. 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.primaryidentifier | https://doi.org/10.1002/anie.202506305 |
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