Quinone-containing poly(arylene), methods for the manufacture thereof, and use for electrochemical gas separation
A quinone-containing poly(arylene) includes repeating units of formula (I), (II), (III), (IV), (V), or (VI) as defined herein. The quinone-containing poly(arylene) can be useful in composites, electrode assemblies, electrochemical cells, gas separation systems, energy storage devices, and electrochromic devices.
1. A quinone-containing poly(arylene) comprising repeating units of at least one of formulas (I) to (III)
wherein R 1 , R 2 , R 3 , R 4 , R 6 and R 7 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group; and
Ar is a substituted or unsubstituted C 6-20 arylene group; and
n is 0 or 1.
2. The quinone-containing poly(arylene) of claim 1 , wherein n is 1 and Ar is a substituted or unsubstituted phenylene group, and the quinone-containing poly(arylene) comprises repeating units of at least one of formulas (Ia) to (IIIa)
wherein R 1 , R 2 , R 3 , R 4 , R 6 and R 7 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
R 5 is independently at each occurrence halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group; and
m is 0 to 4.
3. The quinone-containing poly(arylene) of claim 2 , wherein the quinone-containing poly(arylene) comprises repeating units according to at least one of Formula (Ia) and (IIa), wherein each of R 1 , R 2 , R 3 , and R 4 is hydrogen and m is 0.
4. The quinone-containing poly(arylene) of claim 2 , wherein the quinone-containing poly(arylene) comprises repeating units according to Formula (IIIa), wherein R 6 and R 7 are nitrile and m is 0.
5. The quinone-containing poly(arylene) of claim 1 , wherein the quinone-containing poly(arylene) comprises at least 5 repeating units according to at least one of Formulas (I)-(III).
6. The quinone-containing poly(arylene) of claim 1 , wherein at least 50 mole percent of the repeating units are according to Formula (I), (II), or (III).
7. The quinone-containing poly(arylene) of claim 1 , wherein the quinone-containing poly(arylene) has a binding constant with carbon dioxide of at least 10 1 M −1 .
8. The quinone-containing poly(arylene) of claim 1 , wherein the quinone-containing poly(arylene) has a number average molecular weight of 1,000 to 200,000 grams per mole.
9. A composite comprising the quinone-containing poly(arylene) of claim 1 disposed on a substrate.
10. The composite of claim 9 , wherein the substrate comprises a carbonaceous material.
11. An electrode assembly comprising:
a porous separator; and
the composite of claim 9 .
12. An electrochemical cell comprising the composite of claim 9 .
13. The electrochemical cell of claim 12 , comprising:
a first electrode comprising the composite of claim 11 ;
a second electrode comprising a complementary electroactive composite layer; and
a first separator between the first electrode and the second electrode.
14. The electrochemical cell of claim 12 , wherein the composite further comprises an electrolyte.
15. An energy storage device comprising the quinone-containing poly(arylene) of claim 1 .
16. The quinone-containing poly(arylene) of claim 1 , wherein Ar is a substituted or unsubstituted phenylene group, a substituted or unsubstituted fluorene group, or a combination thereof.
17. A method of making the quinone-containing poly(arylene) of claim 2 , the method comprising combining
a dihalogenated naphthoquinone; and
a benzene diboronic acid or a benzene diboronic ester; in the presence of a palladium catalyst under conditions effective to provide the quinone-containing poly(arylene).
18. A gas separation system comprising:
a plurality of electrochemical cells in fluid communication with a gas inlet and a gas outlet, wherein each of the plurality of electrochemical cells comprises
a first electrode comprising a composite;
a second electrode comprising a complementary electroactive composite layer; and
a first separator between the first electrode and the second electrode;
wherein the composite of the first electrode comprises a quinone-containing poly(arylene) disposed on a substrate, the quinone-containing poly(arylene) comprising
repeating units of at least one of formulas (I) to (VI)
wherein R 1 , R 2 , R 3 , R 4 , R 6 and R 7 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
R 8 and R 9 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
Ar is a substituted or unsubstituted C 6-20 arylene group; and
n is 0 or 1.
19. An electrochromic device comprising a quinone-containing poly(arylene) comprising repeating units of at least one of formulas (I) to (IVI)
wherein R 1 , R 2 , R 3 , R 4 , R 6 and R 7 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
Ar is a substituted or unsubstituted C 6-20 arylene group; and
n is 0 or 1.
20. A quinone-containing poly(arylene) comprising at least 5 repeating units of formula (IV)
wherein R 8 and R 9 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
Ar a substituted or unsubstituted C 6-20 arylene group; and
n is 0 or 1.
21. A quinone-containing poly(arylene) comprising repeating units of formula (IV)
wherein R 8 and R 9 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
Ar is a substituted or unsubstituted phenylene group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted thiophene group, or a combination thereof; and
n is 1.
22. An energy storage device comprising the quinone-containing poly(arylene) of claim 21 .
23. A quinone-containing poly(arylene) comprising repeating units of at least one of formulas (I) to (III) and (VI)
wherein R 1 , R 2 , R 3 , R 4 , R 6 and R 7 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
R 8 and R 9 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
Ar is a substituted or unsubstituted thiophene group; and
n is 1.
24. A quinone-containing poly(arylene) comprising repeating units of formula (VI)
wherein R 8 and R 9 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
Ar is a substituted or unsubstituted C 6-20 arylene group; and
n is 1.
25. The quinone-containing poly(arylene) of claim 24 , wherein n is 1 and Ar is a substituted or unsubstituted phenylene group, and the quinone-containing poly(arylene) comprises repeating units of formula (VIa)
wherein R 5 is independently at each occurrence halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
R 8 and R 9 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group; and
m is 0 to 4.
26. The quinone-containing poly(arylene) of claim 25 , wherein R 8 and R 9 are C 1-6 alkyl groups.
27. An electrochromic device comprising a quinone-containing poly(arylene) comprising repeating units of at least one of formulas (IV) or (VI)
wherein R 8 and R 9 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
Ar is a substituted or unsubstituted C 6-20 arylene group; and
n is 1.
28. An energy storage device comprising a quinone-containing poly(arylene) comprising repeating units of at least one of formulas (V) or (VI)
wherein R 8 and R 9 are independently at each occurrence hydrogen, halogen, a C 1-30 alkyl group, a C 1-30 alkoxy group, a poly(C 1-30 alkylene oxide) group; a C 3-30 cycloalkyl group, a C 3-30 branched alkyl group, a C 6-30 aryl group, a C 3-30 heteroaryl group, a C 1-30 fluoroalkyl group, a nitrile group, a nitro group, a hydroxyl group, a carboxylic acid group, a thiol group, or a vinyl group;
Ar is a substituted or unsubstituted C 6-20 arylene group; and
n is 1.