Core-modified N-confused pentaphyrin variants with adaptive (anti)aromaticity

The retrosynthetic design and syntheses of three unprecedented core-modified N-confused pentaphyrins (sapphyrins) possessing an E-ethylene bithiophene moiety with tunable Hückel (anti)aromaticity are reported. Solution-state spectroscopic analyses reveal the sustained E-conformation for the ethylen...

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Hauptverfasser: Jana, Manik (VerfasserIn) , Velmurugan, Gunasekaran (VerfasserIn) , Sahoo, Sumit (VerfasserIn) , Comba, Peter (VerfasserIn) , Rath, Harapriya (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 28 August 2025
In: Organic chemistry frontiers
Year: 2025, Jahrgang: 12, Heft: 24, Pages: 6885-6893
ISSN:2052-4129
DOI:10.1039/D5QO01088H
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1039/D5QO01088H
Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2025/qo/d5qo01088h
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Verfasserangaben:Manik Jana, Gunasekaran Velmurugan, Sumit Sahoo, Peter Comba and Harapriya Rath
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Zusammenfassung:The retrosynthetic design and syntheses of three unprecedented core-modified N-confused pentaphyrins (sapphyrins) possessing an E-ethylene bithiophene moiety with tunable Hückel (anti)aromaticity are reported. Solution-state spectroscopic analyses reveal the sustained E-conformation for the ethylene moiety. All three N-confused pentaphyrins exhibited vis-NIR absorption. All possible stereoisomers of the S2N3 hybrid N-confused pentaphyrins 14-16 have been unravelled via thorough DFT studies. DFT studies support the Hückel π aromaticity of pentaphyrins 14 and 16 but π-antiaromaticity for 15.
Beschreibung:Gesehen am 19.01.2026
Beschreibung:Online Resource
ISSN:2052-4129
DOI:10.1039/D5QO01088H