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

Nagalexmi Mamveedu Saji; Madeleine R. Taylor; Daniel M. Mazzucato; Paul J. Low; Li Feng Lim; Nicholas Cox; Nicholas F. Chilton; Stephen A. Moggach; Gemma F. Turner; Marcus J. Giansiracusa; Colette Boskovic; Curtis C. Ho; Stuart C. Thickett; Melissa K. Stanfield; Alex C. Bissember; Rebecca O. Fuller

doi:10.1021/acs.orglett.4c02854

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

Nagalexmi Mamveedu Saji
, Madeleine R. Taylor
, Daniel M. Mazzucato
, Paul J. Low
, Li Feng Lim
, Nicholas Cox
, Nicholas F. Chilton
, Stephen A. Moggach
, Gemma F. Turner
, Marcus J. Giansiracusa
, Colette Boskovic
, Curtis C. Ho
, Stuart C. Thickett
, Melissa K. Stanfield
, Alex C. Bissember
, Rebecca O. Fuller

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	8696-8701
Number of pages	6
Journal	Organic Letters
Volume	26
Issue number	41
Early online date	10 Oct 2024
DOIs	https://doi.org/10.1021/acs.orglett.4c02854
Publication status	Published - 18 Oct 2024

Funding

Funders	Funder number
ARC Australian Research Council	DE180100112, FT200100049, FT200100243, FT220100096, FT190100293, LE21010009

Access to Document

10.1021/acs.orglett.4c02854

Cite this

Mamveedu Saji, N., Taylor, M. R., Mazzucato, D. M., Low, P. J., Lim, L. F., Cox, N., Chilton, N. F., Moggach, S. A., Turner, G. F., Giansiracusa, M. J., Boskovic, C., Ho, C. C., Thickett, S. C., Stanfield, M. K., Bissember, A. C., & Fuller, R. O. (2024). Synthesis, Structure, and Redox Properties of Nonsymmetric 6-Oxoverdazyls. Organic Letters, 26(41), 8696-8701. https://doi.org/10.1021/acs.orglett.4c02854

@article{10989b8d80ef4c6bb8acecfbb62aaf0a,

title = "Synthesis, Structure, and Redox Properties of Nonsymmetric 6-Oxoverdazyls",

abstract = "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.",

author = "\{Mamveedu Saji\}, Nagalexmi and Taylor, \{Madeleine R.\} and Mazzucato, \{Daniel M.\} and Low, \{Paul J.\} and Lim, \{Li Feng\} and Nicholas Cox and Chilton, \{Nicholas F.\} and Moggach, \{Stephen A.\} and Turner, \{Gemma F.\} and Giansiracusa, \{Marcus J.\} and Colette Boskovic and Ho, \{Curtis C.\} and Thickett, \{Stuart C.\} and Stanfield, \{Melissa K.\} and Bissember, \{Alex C.\} and Fuller, \{Rebecca O.\}",

year = "2024",

month = oct,

day = "18",

doi = "10.1021/acs.orglett.4c02854",

language = "English",

volume = "26",

pages = "8696--8701",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "Rubber Division of the American Chemical Society",

number = "41",

}

Mamveedu Saji, N, Taylor, MR, Mazzucato, DM, Low, PJ, Lim, LF, Cox, N, Chilton, NF, Moggach, SA, Turner, GF, Giansiracusa, MJ, Boskovic, C, Ho, CC, Thickett, SC, Stanfield, MK, Bissember, AC & Fuller, RO 2024, 'Synthesis, Structure, and Redox Properties of Nonsymmetric 6-Oxoverdazyls', Organic Letters, vol. 26, no. 41, pp. 8696-8701. https://doi.org/10.1021/acs.orglett.4c02854

TY - JOUR

T1 - Synthesis, Structure, and Redox Properties of Nonsymmetric 6-Oxoverdazyls

AU - Mamveedu Saji, Nagalexmi

AU - Taylor, Madeleine R.

AU - Mazzucato, Daniel M.

AU - Low, Paul J.

AU - Lim, Li Feng

AU - Cox, Nicholas

AU - Chilton, Nicholas F.

AU - Moggach, Stephen A.

AU - Turner, Gemma F.

AU - Giansiracusa, Marcus J.

AU - Boskovic, Colette

AU - Ho, Curtis C.

AU - Thickett, Stuart C.

AU - Stanfield, Melissa K.

AU - Bissember, Alex C.

AU - Fuller, Rebecca O.

PY - 2024/10/18

Y1 - 2024/10/18

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85206957107

U2 - 10.1021/acs.orglett.4c02854

DO - 10.1021/acs.orglett.4c02854

M3 - Article

C2 - 39387825

AN - SCOPUS:85206957107

SN - 1523-7052

VL - 26

SP - 8696

EP - 8701

JO - Organic Letters

JF - Organic Letters

IS - 41

ER -

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

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

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