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US 12,630,500 B2Granted
Hexasubstituted radialene compounds and applications thereof
AssigneeThe University of North Carolina At Charlotte Nc
InventorChristopher Bejger
Life of this patent
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Abstract
Hexasubstituted [3] radialene compounds are described herein. In some embodiments, the hexasubstituted [3] radialene compounds exhibit desirable water solubility and reversible redox activity in aqueous solutions, thereby facilitating employment of such compounds in aqueous redox flow batteries.
Claims17
A hexasubstituted [3] radialene dianion of Formula II:
- wherein R1 is selected from the group consisting of cycloalkyl-dione, heterocycloalkyl-dione, cycloalkly-trione, and heterocycloalkyl-trione, wherein the cycloalkyl-dione, heterocycloalkyl-dione, cycloalkly-trione, and heterocycloalkyl-trione are optionally substituted with one or more substituents selected from the group consisting of alkyl and sulfanyl;
- and wherein R2 and R3 are independently selected from the group consisting of cyano, —C(O)OR4, —C(O)NR4R5, and heterocyclyl, wherein R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alcohol, glycol, amine, polyalkylene oxide, and sulfonate.
A hexasubstituted [3] radialene dianion of Formula II:
- wherein R1 is of the formula:
- wherein R6 and R7 are independently selected from the group consisting of hydrogen, alkyl, and alkenyl, and Z is NH, CH2, or O;
- and
- wherein R2 and R3 are independently selected from the group consisting of cyano, —C(O)OR4, —C(O)NR4R5, and heterocyclyl, wherein R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alcohol, glycol, amine, polyalkylene oxide, and sulfonate.
1 more element
A hexasubstituted [3] radialene dianion of Formula II:
- wherein R1 is of the formula:
- wherein R8 and R9 are independently selected from the group consisting of hydrogen, alkyl, and alkenyl, and wherein G is CH or N, and wherein X, Y, and Z are independently selected from O and S;
- and
- wherein R2 and R3 are independently selected from the group consisting of cyano, C(O)OR4, —C(O)NR4R5, and heterocyclyl, wherein R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alcohol, glycol, amine, polyalkylene oxide, and sulfonate.
1 more element
An aqueous redox flow battery comprising:
- a hexasubstituted [3] radialene dianion catholyte, wherein at least one substitution of the radialene dianion comprises a moiety selected from the group consisting of ester, amide, amine, alkylene oxide, alkylene glycol, sulfonate, hydroxyl, and heterocyclyl.
An aqueous redox flow battery comprising:
- a hexasubstituted [3] radialene dianion catholyte of Formula I:
- wherein R1 is selected from the group consisting of —C(O)OR4, —C(O)NR4R5, and heterocyclyl;
- and R2 and R3 are independently selected from the group consisting of cyano, —C(O)OR4, —C(O)NR4R5, and heterocyclyl, wherein R4 and R5 are independently selected from the group consisting of hydrogen, alkyl, alcohol, glycol, amine, polyalkylene oxide, and sulfonate, wherein at least two of R1-R3 are the same.
Dependencies are inferred from the claim text.