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Title: 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 Lab. (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):
H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01M - PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
DOE Contract Number:  
AC05-76RL01830
Resource Type:
Patent
Resource Relation:
Patent File Date: 10/03/2018
Country of Publication:
United States
Language:
English

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 = {2020},
month = {3}
}

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