High-solubility thioether quinones
Abstract
Substituted hydroquinones and quinones and methods of synthesizing such compounds are disclosed herein. The substituted hydroquinones have the formula: while the substituted quinones have the corresponding oxidized structure (1,4-benzoquinones). One, two, three, or all four of R1, R2, R3 and R4 comprise a thioether moiety and a sulfonate moiety, and wherein each R1, R2, R3 and R4 that does not comprise a thioether and a sulfonate moiety sulfonate moiety is independently a hydrogen, an alkyl or an electron withdrawing group. The substituted hydroquinones and quinones are soluble in water, stable in aqueous acid solutions, and have a high reduction potential in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.
- Inventors:
- Issue Date:
- Research Org.:
- Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1637791
- Patent Number(s):
- 10597359
- Application Number:
- 16/150,405
- Assignee:
- Wisconsin Alumni Research Foundation (Madison, WI)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
- DOE Contract Number:
- AC05-76RL01830
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 10/03/2018
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE
Citation Formats
Stahl, Shannon S., and Gerken, James B. High-solubility thioether quinones. United States: N. p., 2020.
Web.
Stahl, Shannon S., & Gerken, James B. High-solubility thioether quinones. United States.
Stahl, Shannon S., and Gerken, James B. Tue .
"High-solubility thioether quinones". United States. https://www.osti.gov/servlets/purl/1637791.
@article{osti_1637791,
title = {High-solubility thioether quinones},
author = {Stahl, Shannon S. and Gerken, James B.},
abstractNote = {Substituted hydroquinones and quinones and methods of synthesizing such compounds are disclosed herein. The substituted hydroquinones have the formula: while the substituted quinones have the corresponding oxidized structure (1,4-benzoquinones). One, two, three, or all four of R1, R2, R3 and R4 comprise a thioether moiety and a sulfonate moiety, and wherein each R1, R2, R3 and R4 that does not comprise a thioether and a sulfonate moiety sulfonate moiety is independently a hydrogen, an alkyl or an electron withdrawing group. The substituted hydroquinones and quinones are soluble in water, stable in aqueous acid solutions, and have a high reduction potential in the oxidized form. Accordingly, they can be used as redox mediators in emerging technologies, such as in mediated fuel cells or organic-mediator flow batteries.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Mar 24 00:00:00 EDT 2020},
month = {Tue Mar 24 00:00:00 EDT 2020}
}
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