Air and moisture stable para- and ortho-quinodimethane derivatives derived from bis-N-Heterocyclic olefins

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dc.contributor.authorJana, Subhadip
dc.contributor.authorElvers, Benedict J.
dc.contributor.authorPatsch, Sebastian
dc.contributor.authorSarkar, Pallavi
dc.contributor.authorKrummenacher, Ivo
dc.contributor.authorNayak, Mithilesh Kumar
dc.contributor.authorMaiti, Avijit
dc.contributor.authorChrysochos, Nicolas
dc.contributor.authorPati, Swapan K.
dc.contributor.authorSchulzke, Carola
dc.contributor.authorBraunschweig, Holger
dc.contributor.authorYıldız, Cem Bural
dc.date.accessioned2023-03-13T06:40:13Z
dc.date.available2023-03-13T06:40:13Z
dc.date.issued2023
dc.departmentTeknik Bilimler Meslek Yüksekokulu
dc.description.abstractHerein we report the development of a new methodology for the synthesis of various quinodimethane derivatives under two-electron oxidation of bis-Nheterocyclic olefins linked by different pi-conjugated aromatic spacers. In case of paraand ortho-phenylene bridge, we obtained air and moisture stable diimidazolium paraand ortho-quinodimethane derivatives. Analogues of the para-phenylene spacer such as tetrafluoro-p-phenylene and p-anthracene also led to the corresponding air and moisture stable quinodimethane derivatives. This emphasizes the influence of imidazolium substituents which facilitate the air and moisture stability of the quinodimethane derivatives. Differences were observed for the electron transfer processes: two one-electron vs one two-electron redox transitions between bis-N-heterocyclic olefins and diimidazolium-quinodimethanes depending on the employed pi-conjugated aromatic spacer. The formation of the pi-conjugated radical-cations, transient redox intermediates between bis-N-heterocyclic olefins and diimidazolium-quinodimethanes, was addressed by an EPR investigation.
dc.identifier.doi10.1021/acs.orglett.2c03993
dc.identifier.pmid36662600
dc.identifier.scopusqualityQ1
dc.identifier.urihttps:/dx.doi.org/10.1021/acs.orglett.2c03993
dc.identifier.urihttps://hdl.handle.net/20.500.12451/10333
dc.identifier.wosWOS:000924015100001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.relation.ispartofOrganic Letters
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectElectrolytic Oxidation
dc.titleAir and moisture stable para- and ortho-quinodimethane derivatives derived from bis-N-Heterocyclic olefins
dc.typeArticle

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