US 11,731,945 B2
Redox-active compounds and uses thereof
Peter Geigle, Alzenau (DE); Jan Hartwig, Alzenau (DE); Evgeny Larionov, Hanau (DE); and Eduard Baal, Offenbach (DE)
Assigned to CMBLU Energy AG, Alzenau (DE)
Appl. No. 17/267,923
Filed by CMBLU PROJEKT AG, Alzenau (DE)
PCT Filed Aug. 14, 2019, PCT No. PCT/EP2019/071887
§ 371(c)(1), (2) Date Feb. 11, 2021,
PCT Pub. No. WO2020/035548, PCT Pub. Date Feb. 20, 2020.
Claims priority of application No. PCT/EP2018/072075 (WO), filed on Aug. 14, 2018.
Prior Publication US 2021/0253540 A1, Aug. 19, 2021
Int. Cl. C07D 241/46 (2006.01); H01M 8/18 (2006.01)
CPC C07D 241/46 (2013.01) [H01M 8/18 (2013.01)] 24 Claims
 
1. A redox flow battery, comprising a substituted low molecular weight aromatic compound or a composition comprising the compound, wherein the compound is characterized by any one of General Formulas (3)-(6);

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein,
each R1-R4 in General Formula (3),
each R1-R6 in General Formula (4),
each R1-R6 in General Formula (5), and
each R1-R8 in General Formula (6)
is independently selected from
—H, -Alkyl, -AlkylGa, -Aryl, —SO3H, —SO3−, —SO3H/—SO3−, —PO3H2, —OH, —OGa, —SH, -Amine, —NH2, —CHO, —COOH, —COOGa, —CN, —CONH2, —CONHGa, —CONGa2, -Heteroaryl, -Heterocycyl, NOGa, —N+OGa, —F, —Cl, and —Br, or are joined together to form a saturated or an unsaturated carbocycle;
wherein each Ga is independently selected from
—H, -Alkyl, -AlkylGb, -Aryl, —SO3H, —SO3−, —PO3H2, —OH, —OAlkyl, —OOH, —OOAlkyl, —SH, —SAlkyl, —NH2, —NHAlkyl, —NAlkyl2, —NAlkyl3+, —NHGb, —NGb2, —NGb3+, —CHO, —COOH, —COOAlkyl, —CN, —CONH2, —CONHAlkyl, —CONAlkyl2, -Heteroaryl, -Heterocycyl, —NOGb, —N+OAlkyl, —F, —Cl, and —Br;
wherein each Gb is independently selected from
—H, -Alkyl, -Aryl, —SO3H, —SO3−1, —PO3H2, —OH, —OAlkyl, —OOH, —OOAlkyl, —SH, —SAlkyl, —NH2, —NHAlkyl, —NAlkyl2, —NAlkyl3+, —CHO, —COOH, —COOAlkyl, —CN, —CONH2, —CONHAlkyl, —CONAlkyl2, -Heteroaryl, -Heterocycyl, —N+OAlkyl, —F, —Cl, and —Br;
wherein the compound comprises a —SO3H/—SO3− group and at least one other substituent selected from the group consisting of an alkoxy group, a hydroxyl group, an amino group, and a carboxyl group.