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

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dc.contributor.authorKrzeszewski, Maciej
dc.contributor.authorDobrzycki, Łukasz
dc.contributor.authorSobolewski, Andrzej L.
dc.contributor.authorCyrański, Michał K.
dc.contributor.authorGryko, Daniel T.
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciencesen
dc.contributor.organizationFaculty of Chemistry, University of Warsawen
dc.contributor.organizationInstitute of Physics, Polish Academy of Sciencesen
dc.date.accessioned2023-08-02T14:59:14Z
dc.date.available2023-08-02T14:59:14Z
dc.date.issued2023
dc.description.abstractA 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 oddmembered-ring defects entails a negative Gaussian curvature within its surface with a significant distortion from planarity (saddle height z 4.3 °A). 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 oneelectron followed by one two-electron) with an exceptionally low first oxidation potential of Eox1 = −0.38 V (vs. Fc/Fc+).en
dc.description.sponsorshipNational Science Centre, Poland (OPUS 2020/37/B/ST4/00017); Foundation for Polish Science (TEAM POIR.04.04.00-00-3CF4/16-00 and START scholarship no. 039.2017; scholarship awarded by the Polish Ministry of Education and Science to outstanding young scientists.
dc.identifier.citationChem. Sci., 2023, 14, 2353–2360 ; https://doi.org/10.1039/D2SC05858Hen
dc.identifier.doi10.1039/D2SC05858H
dc.identifier.issn2041-6539
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/22789
dc.language.isoen
dc.publisherRoyal Society of Chemistryen
dc.rightsUznanie autorstwa-Użycie niekomercyjne 3.0 Polska*
dc.rights.urihttp://creativecommons.org/licenses/by-nc/3.0/pl/*
dc.titleSaddle-shaped aza-nanographene with multiple odd-membered ringsen
dc.typearticleen
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