Twofold 6π-Electrocyclization as a Route Toward Multi-Heteroatom-Doped Nanographenes Built on a 1,4-Dihydropyrrolo[3,2-b]pyrrole Core

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dc.contributor.authorGórski, Krzysztof
dc.contributor.authorPejov, Ljupcho
dc.contributor.authorJørgensen, Kåre B.
dc.contributor.authorKnysh, Iryna
dc.contributor.authorJacquemin, Denis
dc.contributor.authorGryko, Daniel T.
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciences
dc.contributor.organizationInstitute of Chemistry, Faculty of Natural Sciences and Mathematics, SS Cyril and Methodius University, North Macedonia
dc.contributor.organizationEnvironmental and Resource Management Program, The Polytechnic School, Ira A. Fulton Schools of Engineering, Arizona State University, USA
dc.contributor.organizationFaculty of Science and Technology, University of Stavanger, Norway
dc.contributor.organizationNantes Université, CNRS, France
dc.contributor.organizationInstitut Universitaire de France, France
dc.date.accessioned2025-08-25T11:20:37Z
dc.date.available2025-08-25T11:20:37Z
dc.date.issued2025
dc.description.abstractHere we present a highly versatile synthetic strategy based on twofold 6π-electrocyclization accompanied with HBr elimination as a novel approach towards centrosymmetric multi-heteroatom-doped nanographenes build around an electron-rich 1,4-dihydropyrrolo[3,2-b]pyrrole core. A straightforward synthesis from readily available substrates offers a unique possibility of fusing the 1,4-dihydropyrrolo[3,2-b]pyrrole subunit not only with carbocyclic building blocks, such as electron-deficient phenanthrenes, chrysenes, or [4]helicenes, but also with heterocyclic systems, such as benzo[b]furan and 5-thiatruxene. The clear advantage of this strategy is that there is no requirement to assemble complex scaffolds possessing bromoaryl units since bromine atom is introduced by bromination of 1,4-dihydropyrrolo[3,2-b]pyrrole core which, because of its exceptionally electron-rich character, is straightforward reaction. The obtained χ-shaped and S-shaped nanographenes containing 10 or more fused rings, exhibit visible-range emissions characterized by fluorescence quantum yields reaching 48 %. Computational studies of the reaction mechanism revealed that the 6π-electrocyclization is kinetically favourable over photo-induced direct arylation. Steady-state UV/Visible spectroscopy reveals that upon photoexcitation, the prepared S-shaped N-doped nanographenes undergo mostly radiative relaxation leading to large fluorescence quantum yields. We anticipate that this chemistry will empower the creation of new materials with various functionalities.en
dc.description.sponsorshipEU's Horizon 2020 research and innovation programme under Grant Agreement No 860762; Polish National Science Centre (OPUS 2020/37/B/ST4/00017); French Agence Nationale de la Recherche (ANR), Contract No. ANR-20-CE29-0005 (BSE-Forces); Maria Skłodowska-Curie and Pierre Curie Polish-French Science Award.
dc.identifier.citationChem. Eur. J. 2025, 31, e202404094 (1 of 10) // https://doi.org/10.1002/chem.202404094
dc.identifier.doi10.1002/chem.202404094
dc.identifier.issn0947-6539
dc.identifier.issn1521-3765
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/26073
dc.language.isoen
dc.publisherWiley-VCH GmbH
dc.rightsUznanie autorstwa-Użycie niekomercyjne 4.0 Międzynarodoween
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/
dc.sourceChemistry – A European Journal
dc.subjectdyes/pigmentsen
dc.subjectphotochemistryen
dc.subjectnanographenesen
dc.subjectpyrroleen
dc.subjectfluorescenceen
dc.titleTwofold 6π-Electrocyclization as a Route Toward Multi-Heteroatom-Doped Nanographenes Built on a 1,4-Dihydropyrrolo[3,2-b]pyrrole Coreen
dc.typearticle
dc.type.versionpublishedVersion
person.identifier.orcidGryko, Daniel T. [0000-0002-2146-1282]
person.identifier.orcidKnysh, Iryna [0000-0001-8420-9431]
person.identifier.orcidGryko, Daniel T. [0000-0002-2146-1282]
person.identifier.orcidGórski, Krzysztof [0000-0002-6439-2651]
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