Tuning the reduction potential of quinones by controlling the effects of hydrogen bonding, protonation and proton-coupled electron transfer reactions

Raymond R.S. Shi; Malcolm E. Tessensohn; Sherman J.L. Lauw; Nicolette A.B.Y. Foo; Richard D. Webster

doi:10.1039/c8cc09188a

Tuning the reduction potential of quinones by controlling the effects of hydrogen bonding, protonation and proton-coupled electron transfer reactions

Raymond R.S. Shi, Malcolm E. Tessensohn, Sherman J.L. Lauw, Nicolette A.B.Y. Foo, Richard D. Webster^*

^*Corresponding author for this work

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

20 Citations (Scopus)

Abstract

An all-organic cell comprising 2,3-dimethyl-1,4-napthoquinone and pyrano[3,2-f]chromene as electroactive elements exhibited a good combination of large cell voltage and stability of the reduced quinone upon the addition of diethyl malonate (a weak organic acid), as compared to the addition of trifluoroethanol (which led to a high cell potential but low stability via strong hydrogen bonding interactions) and the addition of trifluoroacetic acid (which led to a lower cell potential but high stability through proton transfer).

Original language	English
Pages (from-to)	2277-2280
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	16
DOIs	https://doi.org/10.1039/c8cc09188a
Publication status	Published - 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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abstract = "An all-organic cell comprising 2,3-dimethyl-1,4-napthoquinone and pyrano[3,2-f]chromene as electroactive elements exhibited a good combination of large cell voltage and stability of the reduced quinone upon the addition of diethyl malonate (a weak organic acid), as compared to the addition of trifluoroethanol (which led to a high cell potential but low stability via strong hydrogen bonding interactions) and the addition of trifluoroacetic acid (which led to a lower cell potential but high stability through proton transfer).",

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AU - Shi, Raymond R.S.

AU - Tessensohn, Malcolm E.

AU - Lauw, Sherman J.L.

AU - Foo, Nicolette A.B.Y.

AU - Webster, Richard D.

PY - 2019

Y1 - 2019

N2 - An all-organic cell comprising 2,3-dimethyl-1,4-napthoquinone and pyrano[3,2-f]chromene as electroactive elements exhibited a good combination of large cell voltage and stability of the reduced quinone upon the addition of diethyl malonate (a weak organic acid), as compared to the addition of trifluoroethanol (which led to a high cell potential but low stability via strong hydrogen bonding interactions) and the addition of trifluoroacetic acid (which led to a lower cell potential but high stability through proton transfer).

AB - An all-organic cell comprising 2,3-dimethyl-1,4-napthoquinone and pyrano[3,2-f]chromene as electroactive elements exhibited a good combination of large cell voltage and stability of the reduced quinone upon the addition of diethyl malonate (a weak organic acid), as compared to the addition of trifluoroethanol (which led to a high cell potential but low stability via strong hydrogen bonding interactions) and the addition of trifluoroacetic acid (which led to a lower cell potential but high stability through proton transfer).

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Tuning the reduction potential of quinones by controlling the effects of hydrogen bonding, protonation and proton-coupled electron transfer reactions

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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