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Functionalization of the "Bay Region" of Perylene in Reaction with 1-Arylalk-2-yn-1-ones Catalyzed by Trifluoromethanesulfonic Acid: One-Step Approach to 1-Acyl-2-alkylbenzo[ghi]perylenes

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dc.abstract.enWe describe a convenient method of the synthesis of 1-acyl-2-alkylbenzo[ghi]perylenes via functionalization of the “bay region” of perylene in the reaction with 1-arylalk-2-yn-1-ones catalyzed by trifluoromethanesulfonic acid. We showed that the formation of 1-acyl-2-alkylbenzo[ghi]perylenes from perylene and 1-arylalk-2-yn-1-ones might occur via spontaneous aromatization of 1-acyl-2-alkyl-2a,12a-dihydrogenbenzo[ghi]perylenes by oxidation with dioxygen or by the hydrogen transfer to 1-arylalk-2-yn-1-ones. These compounds are fluorescent in solution with a high Stokes shift and with a ΦF value of up to 0.17 (and 0.36 in solid).
dc.affiliationUniwersytet Warszawski
dc.contributor.authorPlażuk, Damian
dc.contributor.authorGłodek, Marta
dc.contributor.authorMakal, Anna
dc.date.accessioned2024-01-25T01:40:13Z
dc.date.available2024-01-25T01:40:13Z
dc.date.issued2018
dc.description.financeNie dotyczy
dc.description.number22
dc.description.volume83
dc.identifier.doi10.1021/ACS.JOC.8B02280
dc.identifier.issn0022-3263
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/107613
dc.identifier.weblinkhttps://pubs.acs.org/doi/10.1021/acs.joc.8b02280
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.pages14165-14174
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.enPerylene
dc.subject.enBay region
dc.subject.entrifluoromethanesulfonic Acid
dc.subject.enDiels-Alder reaction
dc.titleFunctionalization of the "Bay Region" of Perylene in Reaction with 1-Arylalk-2-yn-1-ones Catalyzed by Trifluoromethanesulfonic Acid: One-Step Approach to 1-Acyl-2-alkylbenzo[ghi]perylenes
dc.typeJournalArticle
dspace.entity.typePublication