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1. (WO2018160618) HIGH-AND LOW-POTENTIAL, WATER-SOLUBLE, ROBUST QUINONES

Pub. No.:    WO/2018/160618    International Application No.:    PCT/US2018/020086
Publication Date: Sat Sep 08 01:59:59 CEST 2018 International Filing Date: Thu Mar 01 00:59:59 CET 2018
IPC: C07F 9/572
C07F 9/6503
C07D 231/12
C07F 9/6561
C07C 309/03
C07C 309/04
C07C 309/09
C07C 309/13
C07C 309/29
C07C 309/42
C07D 403/10
C07D 403/14
C07D 487/04
C07D 487/22
C07D 495/04
C07D 209/48
C07D 285/01
C07D 513/22
C07F 9/38
H01B 1/12
H01M 8/1032
H01M 8/1034
H01M 8/1039
H01M 8/18
H01M 10/00
Applicants: WISCONSIN ALUMNI RESEARCH FOUNDATION
Inventors: STAHL, Shannon, S.
GERKEN, James, B.
ANSON, Colin, W.
SUH, Sung-Eun
STAMOULIS, Alexiouis, G.
Title: HIGH-AND LOW-POTENTIAL, WATER-SOLUBLE, ROBUST QUINONES
Abstract:
Substituted hydroquinones, 1,4-quinones, catechols, 1,2-quinones, anthraquinones, and anthrahydroquinones are disclosed herein. The substituted hydroquinones and catechols have the formula: while the substituted 1,4-quinones or 1,2-have the corresponding oxidized structure (1,4- benzoquinones and 1,2-benzoquinones). One or more of R1, R2, R3 and R4 include a sulfonate moiety, a sulfonimide moiety, or a phosphonate moiety, and any of R1, R2, R3 and R4 that do not include one of these moieties include an alkyl, a cycloalkyl, a thioether, a sulfoxide, a sulfone, a haloalkyl, a halogen, a nitrile, an imide, a pyrazole, or combinations thereof. The substituted anthraquinones have the formula: while the substituted anthrahydroquinones have the corresponding reduced structure. One or more of R1-R8 have a sulfonate or phosphate tethered to the ring by a thi other, amine, or ether including one or more alkyl groups. Any of R1-R8 that do not contain one of these moieties include an alkyl, a cycloalkyl, a thiother, a sulfoxide, a sulfone, a haloalkyl, a halogen, a hydroxyl, an alkoxyl, an ether, an amine, or hydrogen The substituted hydroquinones, 1,4-quinones, catechols, 1,2-quinones, anthraquinones, or anthrahydroquinones are soluble in water, stable in aqueous acid solutions, and have useful reduction potentials 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.