Synthesis, Structure, and Redox Properties of Nonsymmetric 6‑Oxoverdazyls

Synthesis, Structure, and Redox Properties of Nonsymmetric 6‑Oxoverdazyls

Nonsymmetric 6π-electron (“oxidized”) 6-oxoverdazyls have been synthesized for the first time. After formal incorporation of a hydrogen atom, the corresponding 7π-electron neutral verdazyl radical is generated. The 7π radical can undergo a further electrochemically reversible reduction to an 8π anio...

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Veröffentlicht in:Organic letters 2024-10, Vol.26 (41), p.8696-8701
Hauptverfasser: Mamveedu Saji, Nagalexmi, Taylor, Madeleine R., Mazzucato, Daniel M., Low, Paul J., Lim, Li Feng, Cox, Nicholas, Chilton, Nicholas F., Moggach, Stephen A., Turner, Gemma F., Giansiracusa, Marcus J., Boskovic, Colette, Ho, Curtis C., Thickett, Stuart C., Stanfield, Melissa K., Bissember, Alex C., Fuller, Rebecca O.
Format: Artikel
Sprache:eng
Schlagworte:
electrochemistry
hydrogen
species
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Zusammenfassung:Nonsymmetric 6π-electron (“oxidized”) 6-oxoverdazyls have been synthesized for the first time. After formal incorporation of a hydrogen atom, the corresponding 7π-electron neutral verdazyl radical is generated. The 7π radical can undergo a further electrochemically reversible reduction to an 8π anion. Both redox processes occur at more moderate potentials than the parent verdazyl, tuning the accessible potential windows of 6π, 7π, and 8π verdazyl species.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02854