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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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Autores principales: Jana, Manik (Autor) , Velmurugan, Gunasekaran (Autor) , Sahoo, Sumit (Autor) , Comba, Peter (Autor) , Rath, Harapriya (Autor)
Formato: Article (Journal)
Lenguaje:inglés
Publicado: 28 August 2025
In: Organic chemistry frontiers
Year: 2025, Volumen: 12, Número: 24, Pages: 6885-6893
ISSN:2052-4129
DOI:10.1039/D5QO01088H
Acceso en línea: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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Notas de Autor:Manik Jana, Gunasekaran Velmurugan, Sumit Sahoo, Peter Comba and Harapriya Rath
Descripción
Sumario: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.
Notas:Gesehen am 19.01.2026
Descripción Física:Online Resource
ISSN:2052-4129
DOI:10.1039/D5QO01088H

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