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Potent strategy towards strongly emissive nitroaromatics through a weakly electron-deficient core

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cris.lastimport.scopus2024-02-12T19:01:10Z
dc.abstract.enNitroaromatics seldom fluoresce. The importance of electron-deficient (n-type) conjugates, however, has inspired a number of strategies for suppressing the emission-quenching effects of the strongly electron-withdrawing nitro group. Here, we demonstrate how such strategies yield fluorescent nitroaryl derivatives of dipyrrolonaphthyridinedione (DPND). Nitro groups near the DPND core quench its fluorescence. Conversely, nitro groups placed farther from the core allow some of the highest fluorescence quantum yields ever recorded for nitroaromatics. This strategy of preventing the known processes that compete with photoemission, however, leads to the emergence of unprecedented alternative mechanisms for fluorescence quenching, involving transitions to dark nπ* singlet states and aborted photochemistry. Forming nπ* triplet states from ππ* singlets is a classical pathway for fluorescence quenching. In nitro-DPNDs, however, these ππ* and nπ* excited states are both singlets, and they are common for nitroaryl conjugates. Understanding the excited-state dynamics of such nitroaromatics is crucial for designing strongly fluorescent electron-deficient conjugates.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorMierzwa, Dominik
dc.contributor.authorPORONIK, Yevgen
dc.contributor.authorKaliszewska, Marzena
dc.contributor.authorPiatkowski, Piotr
dc.contributor.authorSadowski, Bartłomiej
dc.contributor.authorVullev, Valentine I.
dc.contributor.authorGryko, Daniel
dc.contributor.authorLohrey, Trevor D.
dc.contributor.authorClark, John A.
dc.contributor.authorCzichy, Małgorzata
dc.contributor.authorJanasik, Patryk
dc.contributor.authorBanasiewicz, Marzena
dc.contributor.authorGadomski, Wojciech
dc.contributor.authorŁapkowski, Mieczysław
dc.contributor.authorKozankiewicz, Bolesław
dc.contributor.authorSobolewski, Andrzej
dc.date.accessioned2024-01-25T17:17:17Z
dc.date.available2024-01-25T17:17:17Z
dc.date.copyright2021-09-29
dc.date.issued2021
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number42
dc.description.versionFINAL_PUBLISHED
dc.description.volume12
dc.identifier.doi10.1039/D1SC03670J
dc.identifier.issn2041-6520
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/116674
dc.identifier.weblinkhttp://pubs.rsc.org/en/content/articlepdf/2021/SC/D1SC03670J
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemical Science
dc.relation.pages14039-14049
dc.rightsCC-BY-NC
dc.sciencecloudnosend
dc.titlePotent strategy towards strongly emissive nitroaromatics through a weakly electron-deficient core
dc.typeJournalArticle
dspace.entity.typePublication