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High-solubility thioether quinones

Patent ·
OSTI ID:1637791

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.

Research Organization:
Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
AC05-76RL01830
Assignee:
Wisconsin Alumni Research Foundation (Madison, WI)
Patent Number(s):
10,597,359
Application Number:
16/150,405
OSTI ID:
1637791
Country of Publication:
United States
Language:
English

References (2)

New anionic acceptors Br2XQNHCH2SO3− [X=Br, BryCl1−y (y≈0.5), and Cl; Q=1,4-benzoquinone) and their charge-transfer salts journal June 2010
Quinone 1 e and 2 e /2 H + Reduction Potentials: Identification and Analysis of Deviations from Systematic Scaling Relationships journal November 2016

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