Isatin derivative redoxamer for electrochemical device
An electrochemical device includes a compound that is an isatin derivative. The electrochemical device may be a lithium ion battery, a sodium ion battery, or a redox flow battery, and the isatin derivative may be a bipolar redox active material.
1. An electrochemical device comprising a cathode, an anode, and an electrolyte comprising a compound represented by Formula I:
wherein:
R 1 , R 2 , R 3 , R 4 , and R 5 are each independently H, alkyl, haloalkyl, alkoxy, aryl, or polyether; or where any of R 1 , R 2 , R 3 , R 4 , and R 5 is a linker to a polymer backbone, where the linker is absent, a carbonyl, an alkyl ester group, aryl-E, E-aryl, alkylene, or -alkyl-O-alkyl-;
E is an alkylene or alkyl-O-alkyl;
at least one of R 1 , R 2 , R 3 , R 4 , and R 5 is other than H;
when R 1 is H, R 3 is other than methyl.
2. The electrochemical device of claim 1 which is a redox flow battery or lithium ion battery.
3. The electrochemical device of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each independently H, C 1 -C 10 alkyl, C 1 -C 10 alkoxy, C 1 -C 10 haloalkyl, or polyether.
4. The electrochemical device of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each independently H, methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, tert-butyl, or polyether.
5. The electrochemical device of claim 1 , wherein R 1 , R 3 , and R 5 are each independently C 1 -C 10 alkyl, and R 2 and R 4 are H.
6. The electrochemical device of claim 1 , wherein R 1 , R 3 , and R 5 are each independently methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, or tert-butyl; and R 2 and R 4 are H.
7. The electrochemical device of claim 1 , wherein R 1 , R 3 , and R 5 are each independently methyl or ethyl; and R 2 and R 4 are H.
8. The electrochemical device of claim 1 , wherein R 3 is an aryl group of Formulae, where each is a link to a group of Formula I:
9. The electrochemical device of claim 1 , wherein R 3 is an aryl group of Formula II:
wherein R 6 , R 7 , R 8 , and R 9 are each independently H, alkyl, alkoxy, haloalkyl, or polyether, or where any of R 6 , R 7 , R 8 , and R 9 is a linker to a polymer backbone, where the linker is absent, an alkylenyl, an alkyl-O-alkyl, aryl-E, E-aryl, a carbonyl, or a alkyl ester, wherein E is an alkylene or alkyl-O-alkyl.
10. The electrochemical device of claim 1 , wherein R 1 or R 3 is a linker, L, to a polymer backbone, where the linker is absent, a carbonyl, alkylene, aryl-E, E-aryl,-alkyl-O-alkyl-, or a alkyl ester group, wherein E is an alkylenyl or alkyl-O-alkyl.
11. The electrochemical device of claim 10 , wherein the compound is of Formula III, IIIa, or IV:
wherein R is H or alkyl, and n indicates that this is part of a repeat unit in a polymer backbone.
12. The electrochemical device of claim 11 , wherein L is absent, —CH 2 —, -alkyl-O-alkyl, —C(O)—, or —CH 2 CH 2 OC(O)—; and E is —CH 2 —or alkyl-O-alkyl.
13. An electrochemical device comprising:
a catholyte reservoir containing a catholyte material dissolved in a first non-aqueous solvent;
an anolyte reservoir containing an anolyte material dissolved in a second non-aqueous solvent; and
a reaction chamber;
wherein:
the first and second non-aqueous solvents are the same or different;
the catholyte material, the anolyte material, or both the catholyte material and the anolyte material is an isatin derivative compound;
the electrochemical device is a redox flow battery; and
the isatin derivative compound is represented by Formula I:
R 1 , R 2 , R 3 , R 4 , and R 5 are each independently H, alkyl, haloalkyl, alkoxy, aryl, or polyether; or where any of R 1 , R 2 , R 3 , R 4 , and R 5 is a linker to a polymer backbone, where the linker is absent, a carbonyl, aryl-E, E-aryl, an alkyl ester group, alkylene, or -alkyl-O-alkyl-; and
E is an alkylene or alkyl-O-alkyl;
wherein at least one of R 1 , R 2 , R 3 , R 4 , and R 5 is other than H; and
when R 1 is H, R 3 is other than methyl.
14. The electrochemical device of claim 13 , wherein the catholyte and anolyte materials are both the isatin derivative.
15. The electrochemical device of claim 13 , wherein the first and the second non-aqueous solvents are the same.
16. The electrochemical device of claim 13 , wherein the isatin derivative is a compound represented by Formula I:
wherein:
R 1 , R 2 , R 3 , R 4 , and R 5 are each independently H, alkyl, haloalkyl, alkoxy, aryl, or polyether; or where any of R 1 , R 2 , R 3 , R 4 , and R 5 is a linker to a polymer backbone, where the linker is absent, an alkylenyl, an alkyl-O-alkyl, aryl-E, E-aryl, or an alkyl ester group, a alkyl ester, wherein E is an alkylene or alkyl-O-alkyl.
17. An electrochemical device comprising:
a cathode;
an anode;
a separator disposed between the cathode and the anode; and
an electrolyte comprising:
a non-aqueous solvent;
a salt; and
an isatin derivative that is other than isatin and 5-methylisatin;
wherein:
the electrochemical device is a lithium ion battery or a sodium ion battery; and
the isatin derivative is a compound represented by Formula I:
R 1 , R 2 , R 3 , R 4 , and R 5 are each independently H, alkyl, haloalkyl, alkoxy, aryl, or polyether; or where any of R 1 , R 2 , R 3 , R 4 , and R 5 is a linker to a polymer backbone, where the linker is absent, a carbonyl, aryl-E, E-aryl, an alkyl ester group, alkylene, or -alkyl-O-alkyl-; and
E is an alkylene or alkyl-O-alkyl;
wherein at least one of R 1 , R 2 , R 3 , R 4 , and R 5 is other than H; and
when R 1 is H, R 3 is other than methyl.