Rechargeable lithium-ion cell

1. A rechargeable lithium-ion cell having a cell capacity and comprising:

A. a positive electrode having a recharged potential;

B. a negative electrode;

C. a charge-carrying electrolyte comprising a charge-carrying medium and a lithium salt; and

D. a redox shuttle having the following structure:

wherein X is a covalent bond, a sulfur atom (S), or N—R 6 , and wherein each of R 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 , R 9 and R 10 is independently an alkyl group, a haloalkyl group, a perhaloalkyl group, an acyl group, an acyloxy group, an acetyl group, a haloacetyl group, an alkaryl group, an alkoxy group, an acetamido group, an amido group, an aryl group, an aralkyl group, an alkyl carboxyl group, an aryl carboxyl group, an alkylsulfonyl group, a benzoyl group, a carbamoyl group, a carboxy group, a cyano group, a formyl group, a halo group, a haloacetamido group, a haloacyl group, a haloalkylsulfonyl group, a haloaryl group, a methylsulfonyloxyl group, a nitro group, an oxo group, an alkyl ether group, a trialkylammoniumalkyl group, a phosphate group, a phosphonate group, or an alkyl phosphonate group, and wherein one of R 3 and R 4 is optionally a hydrogen atom; and

wherein R 5 is an alkyl group having 1-12 carbon atoms, an alkylether group having 1-12 carbon atoms, or a trialkylammoniumalkyl group having 1-12 carbon atoms.

2. A rechargeable lithium-ion cell having a cell capacity and comprising:

A. a positive electrode having a recharged potential;

B. a negative electrode;

C. a charge-carrying electrolyte comprising a charge-carrying medium and a lithium salt; and

D. a redox shuttle having the following structure:

wherein each of R 1 and R 2 is independently an alkyl group, a haloalkyl group, a perhaloalkyl group, an acyl group, an acyloxy group, an acetyl group, a haloacetyl group, an alkaryl group, an alkoxy group, an acetamido group, an amido group, an aryl group, an aralkyl group, an alkyl carboxyl group, an aryl carboxyl group, an alkylsulfonyl group, a benzoyl group, a carbamoyl group, a carboxy group, a cyano group, a formyl group, a halo group, a haloacetamido group, a haloacyl group, a haloalkylsulfonyl group, a haloaryl group, a methylsulfonyloxyl group, a nitro group, an oxo group, an alkyl ether group, a trialkylammoniumalkyl group, a phosphate group, a phosphonate group, or an alkyl phosphonate group;

wherein each of R 3 and R 4 is independently an alkyl group having 1 to 12 carbon atoms or a haloalkyl group having 1 to 12 carbon atoms and/or one of R 3 and R 4 is a hydrogen atom; and

wherein R 5 is an alkyl group having 1-12 carbon atoms, a haloalkyl group having 1-12 carbon atoms, a perhaloalkyl group having 1-12 carbon atoms, an alkyl ether group having 1-12 carbon atoms, or a trialkylammoniumalkyl group having 1-12 carbon atoms.

3. The rechargeable lithium-ion cell of claim 2 wherein each of R 1 and R 2 is independently an alkyl group having 1-12 carbon atoms or a haloalkyl group having 1-12 carbon atoms.

4. The rechargeable lithium-ion cell of claim 2 wherein each of R 1 and R 2 is independently an alkyl group having 1-6 carbon atoms.

5. The rechargeable lithium-ion cell of claim 2 wherein each of R 3 and R 4 is independently an alkyl group having 1-12 carbon atoms, a haloalkyl group having 1-12 carbon atoms, a acetyl group, a haloacetyl group, or a hydrogen atom.

6. The rechargeable lithium-ion cell of claim 2 wherein each of R 3 and R 4 is independently an alkyl group having 1-6 carbon atoms.

7. The rechargeable lithium-ion cell of claim 2 wherein one of R 3 and R 4 is a hydrogen atom and the other of R 3 and R 4 is not a hydrogen atom.

8. The rechargeable lithium-ion cell of claim 2 wherein R 5 is an alkyl group having 1-12 carbon atoms, an alkylether group having 1-12 carbon atoms, or a trialkylammoniumalkyl group having 1-12 carbon atoms.

9. The rechargeable lithium-ion cell of claim 2 wherein R 5 is an alkyl group having 1-6 carbon atoms.

10. The rechargeable lithium-ion cell of claim 2 wherein said redox shuttle is dissolved in the charge-carrying electrolyte.

11. The rechargeable lithium-ion cell of claim 2 wherein said redox shuttle has an oxidation potential from 3.5 to 5 V as compared to Li/Li + .

12. The rechargeable lithium-ion cell of claim 2 wherein said redox shuttle provides overcharge protection to said rechargeable lithium-ion cell after at least 10 charge-discharge cycles at a charging voltage sufficient to oxidize said redox shuttle and at an overcharge charge flow equivalent to 100% of cell capacity during each charge-discharge cycle.

13. The rechargeable lithium-ion cell of claim 2 wherein said redox shuttle provides overcharge protection to said rechargeable lithium-ion cell after at least 500 charge-discharge cycles at a charging voltage sufficient to oxidize said redox shuttle and at an overcharge charge flow equivalent to 100% of cell capacity during each charge-discharge cycle.

14. The rechargeable lithium-ion cell of claim 2 wherein said redox shuttle is present in an amount from 1 to 10 percent by weight based on a total weight of said charge-carrying electrolyte.

15. The rechargeable lithium-ion cell of claim 2 wherein said positive electrode comprises LiFePO 4 , Li 2 FeSiO 4 , MnO 2 , Li x MnO 2 , LiNiMnCoO 2 , and/or LiNiCoAlO 2 , wherein x is 0.3 to 0.4.

16. The rechargeable lithium-ion cell of claim 2 wherein said negative electrode comprises graphitic carbon, lithium metal or a lithium alloy.

17. The rechargeable lithium-ion cell of claim 2 wherein said charge carrying medium comprises ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethylmethyl carbonate or combinations thereof.

18. A rechargeable lithium-ion cell having a cell capacity and comprising:

A. a positive electrode having a recharged potential;

B. a negative electrode;

C. a charge-carrying electrolyte comprising a charge-carrying medium and a lithium salt; and

D. a redox shuttle having the following structure:

wherein each of R 1 and R 2 is independently an alkyl group, a haloalkyl group, a perhaloalkyl group, or an alkyl ether group;

wherein at least one of R 3 and R 4 is an alkyl group, a haloalkyl group, a perhaloalkyl group, an alkyl ether group, an acyl group, or a haloacyl group; and

wherein R 5 is an alkyl group, an alkyl ether group, a trialkylammoniumalkyl group, an acetyl group, or a CF 3 group.

19. An article comprising the rechargeable lithium-ion cell of claim 2 .

20. An array comprising two or more of said rechargeable lithium-ion cells of claim 2 .

21. The rechargeable lithium-ion cell of claim 18 wherein each of R 1 and R 2 is independently an alkyl group having 1-12 carbon atoms.

22. The rechargeable lithium-ion cell of claim 18 wherein each of R 3 and R 4 is independently an alkyl group having 1-6 carbon atoms or a haloalkyl group having 1-12 carbon atoms.

23. The rechargeable lithium-ion cell of claim 18 wherein said redox shuttle has an oxidation potential from 3.5 to 5 V as compared to Li/Li + .

24. An article comprising the rechargeable lithium-ion cell of claim 18 .

25. An array comprising two or more of said rechargeable lithium-ion cells of claim 18 .