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Saddle-shaped aza-nanographene with multiple odd-membered rings

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cris.lastimport.scopus2024-02-12T19:39:15Z
dc.abstract.enA saddle-shaped aza-nanographene containing a central 1,4-dihydropyrrolo[3,2-b]pyrrole (DHPP) has been prepared via a rationally designed four-step synthetic pathway encompassing intramolecular direct arylation, the Scholl reaction, and finally photo-induced radical cyclization. The target non-alternant, nitrogen-embedded polycyclic aromatic hydrocarbon (PAH) incorporates two abutting pentagons between four adjacent heptagons forming unique 7−7−5−5−7−7 topology. Such a combination of odd-membered-ring defects entails a negative Gaussian curvature within its surface with a significant distortion from planarity (saddle height ≈ 4.3 Å). Its absorption and fluorescence maxima are located in the orange-red region, with weak emission originating from the intramolecular charge-transfer character of a low-energy absorption band. Cyclic voltammetry measurements revealed that this stable under ambient conditions aza-nanographene underwent three fully reversible oxidation steps (two one-electron followed by one two-electron) with an exceptionally low first oxidation potential of Eox1 = −0.38 V (vs. Fc/Fc+).
dc.affiliationUniwersytet Warszawski
dc.contributor.authorGryko, Daniel T.
dc.contributor.authorCyrański, Michał
dc.contributor.authorSobolewski, Andrzej L.
dc.contributor.authorDobrzycki, Łukasz
dc.contributor.authorKrzeszewski, Maciej
dc.date.accessioned2024-01-25T19:34:34Z
dc.date.available2024-01-25T19:34:34Z
dc.date.copyright2023-01-03
dc.date.issued2023
dc.description.accesstimeAT_PUBLICATION
dc.description.financeNie dotyczy
dc.description.number9
dc.description.versionFINAL_PUBLISHED
dc.description.volume14
dc.identifier.doi10.1039/D2SC05858H
dc.identifier.issn2041-6520
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/118962
dc.identifier.weblinkhttp://pubs.rsc.org/en/content/articlepdf/2023/SC/D2SC05858H
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemical Science
dc.relation.pages2353-2360
dc.rightsCC-BY-NC
dc.sciencecloudnosend
dc.titleSaddle-shaped aza-nanographene with multiple odd-membered rings
dc.typeJournalArticle
dspace.entity.typePublication