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Bowl‐Shaped Pentagon‐ and Heptagon‐Embedded Nanographene Containing a Central Pyrrolo[3,2‐ b ]pyrrole Core

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dc.abstract.enA bowl‐shaped nitrogen‐doped nanographene composed of a pyrrolo[3,2‐b]pyrrole core substituted with six arene rings circularly bonded with one another has been prepared via a concise synthetic strategy encompassing the multicomponent tetraarylpyrrolopyrrole (TAPP) synthesis, the Scholl reaction, and intramolecular direct arylation. This synthesis represents the first case of programmed sequential intramolecular direct arylation reactions utilizing the different reactivity of C–Br and C–Cl bonds. The target compound contains two central pentagons confined between two adjacent heptagons—the inverse Stone–Thrower–Wales topology. The presence of both five‐ and seven‐membered rings in the final structure is responsible for interesting properties such as a perpendicularly aligned dipole moment, absorption and fluorescence in the orange‐red region, weak emission originating from the charge‐transfer character of a low‐energy absorption band, and a high lying HOMO. In the solid state slipped convex‐to‐convex π–π stacking dominates.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorKrzeszewski, Maciej
dc.contributor.authorCyrański, Michał
dc.contributor.authorSobolewski, Andrzej
dc.contributor.authorGryko, Daniel
dc.contributor.authorDobrzycki, Łukasz
dc.date.accessioned2024-01-24T18:45:41Z
dc.date.available2024-01-24T18:45:41Z
dc.date.issued2021
dc.description.financePublikacja bezkosztowa
dc.description.number27
dc.description.volume60
dc.identifier.doi10.1002/ANIE.202104092
dc.identifier.issn1433-7851
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/102483
dc.identifier.weblinkhttps://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202104092
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofAngewandte Chemie - International Edition
dc.relation.pages14998-15005
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleBowl‐Shaped Pentagon‐ and Heptagon‐Embedded Nanographene Containing a Central Pyrrolo[3,2‐ b ]pyrrole Core
dc.typeJournalArticle
dspace.entity.typePublication