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Saddle-shaped aza-nanographene with multiple odd-membered rings
cris.lastimport.scopus | 2024-02-12T19:39:15Z |
dc.abstract.en | A 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.affiliation | Uniwersytet Warszawski |
dc.contributor.author | Gryko, Daniel T. |
dc.contributor.author | Cyrański, Michał |
dc.contributor.author | Sobolewski, Andrzej L. |
dc.contributor.author | Dobrzycki, Łukasz |
dc.contributor.author | Krzeszewski, Maciej |
dc.date.accessioned | 2024-01-25T19:34:34Z |
dc.date.available | 2024-01-25T19:34:34Z |
dc.date.copyright | 2023-01-03 |
dc.date.issued | 2023 |
dc.description.accesstime | AT_PUBLICATION |
dc.description.finance | Nie dotyczy |
dc.description.number | 9 |
dc.description.version | FINAL_PUBLISHED |
dc.description.volume | 14 |
dc.identifier.doi | 10.1039/D2SC05858H |
dc.identifier.issn | 2041-6520 |
dc.identifier.uri | https://repozytorium.uw.edu.pl//handle/item/118962 |
dc.identifier.weblink | http://pubs.rsc.org/en/content/articlepdf/2023/SC/D2SC05858H |
dc.language | eng |
dc.pbn.affiliation | chemical sciences |
dc.relation.ispartof | Chemical Science |
dc.relation.pages | 2353-2360 |
dc.rights | CC-BY-NC |
dc.sciencecloud | nosend |
dc.title | Saddle-shaped aza-nanographene with multiple odd-membered rings |
dc.type | JournalArticle |
dspace.entity.type | Publication |