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Octacyano-substituted tridecacyclene: a non-benzenoid cyanocarbon with low-lying LUMO and multistage redox properties

Octacyanated tridecacyclene was synthesized from novel brominated tridecacyclene. In the crystal, the saddle-shaped scaffold exhibits a zigzag packing motif governed by an interplay between the inherent geometry of the central cyclooctatetraene moiety and the hydrogen bonding mediated by the dipolar...

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Hauptverfasser: Misselwitz, Erik (VerfasserIn) , Spengler, Jonas (VerfasserIn) , Rominger, Frank (VerfasserIn) , Kivala, Milan (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 10 Mar 2025
In: Chemical communications
Year: 2025, Jahrgang: 61, Heft: 31, Pages: 5754-5757
ISSN:1364-548X
DOI:10.1039/D5CC00672D
Online-Zugang:Verlag, kostenfrei, Volltext: https://doi.org/10.1039/D5CC00672D
Verlag, kostenfrei, Volltext: https://pubs.rsc.org/en/content/articlelanding/2025/cc/d5cc00672d
Volltext
Verfasserangaben:Erik Misselwitz, Jonas Spengler, Frank Rominger and Milan Kivala
Beschreibung
Zusammenfassung:Octacyanated tridecacyclene was synthesized from novel brominated tridecacyclene. In the crystal, the saddle-shaped scaffold exhibits a zigzag packing motif governed by an interplay between the inherent geometry of the central cyclooctatetraene moiety and the hydrogen bonding mediated by the dipolar cyano functionalities. The compound undergoes five reversible reductions in a particularly narrow potential window of 1.15 V in CH2Cl2. The first reduction occurs at −0.78 V (vs. Fc/Fc+), which corresponds to a remarkably low-lying LUMO of −4.32 eV.
Beschreibung:Zuerst veröffentlicht: 10. März 2025
Gesehen am 26.09.2025
Beschreibung:Online Resource
ISSN:1364-548X
DOI:10.1039/D5CC00672D

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