Compounds may have general Formula IVA or IVB. where, R8, R9, R10, and R11 are each independently selected from H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, and alkoxy groups; X and Y are each independently O, S, N, or P; and Z′ is a linkage between X and Y. Such compounds may be used as redox shuttles
Compounds may have general Formula IVA or IVB. where, R8, R9, R10, and R11 are each independently selected from H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, and alkoxy groups; X and Y are each independently O, S, N, or P; and Z′ is a linkage between X and Y. Such compounds may be used as redox shuttles in electrolytes for use in electrochemical cells, batteries and electronic devices.
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1. An electrolyte comprising: an alkali metal salt;a polar aprotic solvent; anda redox shuttle comprising a compound of Formula IVA or IVB; andwherein: the electrolyte solution is substantially non-aqueous;the compound of Formula IVA or IVB is: R8, R9, R10, and R11 are each independently H, F, Cl, B
1. An electrolyte comprising: an alkali metal salt;a polar aprotic solvent; anda redox shuttle comprising a compound of Formula IVA or IVB; andwherein: the electrolyte solution is substantially non-aqueous;the compound of Formula IVA or IVB is: R8, R9, R10, and R11 are each independently H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, or alkoxy groups;at least two of R8, R9, R10, and R11 are independently tertiary alkyl groups;X and Y are each independently O, S, N, or P; andZ′ is a linkage between X and Y. 2. The electrolyte of claim 1, wherein X and Y are O. 3. The electrolyte of claim 1, wherein: Z′ is CH2, CH2CH2, CH2CH2CH2, CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, CH(CH3)CH2, CH(CH3)(CH2)CH2, CH(CH3)CH(CH3), CHCH, CCl2, CBr2, CF2, CH(Cl)CH(Cl), CH(Br)CH(Br), CH(F)CH(F), CH2(CF2)CH2, CH2N(Me)CH2, CH2OCH2CH2OCH2, CH2CH2OCH2OCH2CH2; CH2CH2OCH2CH2OCH2, or CH2CH2OCH2CH2OCH2CH2. 4. The electrolyte of claim 1, wherein: R8 and R10 are tert-butyl;R9 and R11 are each independently H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, or alkoxy groups;X and Y are O; andZ′ is CH2, CH2CH2, or CHCH. 5. The electrolyte of claim 1, wherein: R8 and R10 are tert-butyl;R9 and R11 are each independently H, F, Cl, or Br;X and Y are O; andZ′ is CH2 or CHCH. 6. The electrolyte of claim 1, wherein the compound comprises 5,7-di-tert-butyl-2,3-dibromo-1,4-benzodioxin; 5,7-di-tert-butyl-1,4-benzodioxin; or 4,6-di-tert-butyl-1,3-benzodioxole. 7. The electrolyte of claim 1, wherein the redox shuttle has a redox potential of from 3 V to 5 V in the electrolyte. 8. The electrolyte of claim 1, wherein the redox shuttle is present in the electrolyte from 0.0005 wt % to 50 wt %. 9. The electrolyte of claim 1, wherein the alkali metal salt is a lithium salt. 10. The electrolyte of claim 1, wherein the alkali metal salt comprises Li[B(C2O4)2]; Li[BF2(C2O4)]; LiClO4; LiBF4; LiAsF6; LiPF6; Li[CF3SO3]; Li[N(CF3SO2)2]; Li[C(CF3SO2)3]; LiN(SO2C2F5)2; or a lithium alkyl fluorophosphate. 11. The electrolyte of claim 1, wherein the polar aprotic solvent comprises ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, dimethyl ether, or γ-butyrolactone. 12. An electrochemical device comprising a cathodean anode; andan electrolyte comprising: an alkali metal salt;a polar aprotic solvent; anda redox shuttle comprising a compound of Formula IVA or IVB;wherein: the electrolyte solution is substantially non-aqueous;the compound of Formula IVA or IVB is: R8, R9, R10, and R11 are each independently H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, or alkoxy groups;at least two of R8, R9, R10, and R11 are independently tertiary alkyl groups;X and Y are each independently O, S, N, or P; andZ′ is a linkage between X and Y. 13. The electrochemical device of claim 12, wherein X and Y are O. 14. The electrochemical device of claim 12, wherein: Z′ is CH2, CH2CH2, CH2CH2CH2, CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, CH(CH3)CH2, CH(CH3)(CH2)CH2, CH(CH3)CH(CH3), CHCH, CCl2, CBr2, CF2, CH(Cl)CH(Cl), CH(Br)CH(Br), CH(F)CH(F), CH2(CF2)CH2, CH2N(Me)CH2, CH2OCH2CH2OCH2, CH2CH2OCH2OCH2CH2; CH2CH2OCH2CH2OCH2, or CH2CH2OCH2CH2OCH2CH2. 15. The electrochemical device of claim 12, wherein: R8 and R10 are tert-butyl;R9 and R11 are each independently H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, or alkoxy groups;X and Y are O; andZ′ is CH2, CH2CH2, or CHCH. 16. The electrochemical device of claim 12, wherein the compound comprises 5,7-di-tert-butyl-2,3-dibromo-1,4-benzodioxin; 5,7-di-tert-butyl-1,4-benzodioxin; or 4,6-di-tert-butyl-1,3-benzodioxole. 17. An electrochemical device comprising a spinel, olivine, or carbon-coated olivine cathode;a graphite or amorphous carbon anode; anda substantially non-aqueous electrolyte comprising: an alkali metal salt comprising Li[BF2(C2O4)] or Li[B(C2O4)2];a polar aprotic solvent comprising ethyl acetate; propyl acetate; ethylene carbonate; propylene carbonate; dimethyl carbonate; diethyl carbonate; ethyl methyl carbonate; dimethyl ether; or γ-butyrolactone;a redox shuttle comprising a compound of Formula IVA or IVB; andan electrode stabilizing additive;wherein: the compound of Formula IVA or IVB is: R8, R9, R10, and R11 are each independently H, F, Cl, Br, CN, NO2, alkyl, haloalkyl, or alkoxy groups;at least two of R8, R9, R10, and R11 are independently tertiary alkyl groups;X and Y are each independently O, S, N, or P; andZ′ is a linkage between X and Y; andthe electrode stabilizing compound comprises pyridazine; vinyl pyridazine; quinoline; vinyl quinoline; pyridine; vinyl pyridine; indole; vinyl indole; triethanolamine; 1,3-dimethyl butadiene; butadiene; vinyl ethylene carbonate; vinyl carbonate; imidazole; vinyl imidazole; piperidine; vinyl piperidine; pyrimidine; vinyl pyrimidine; pyrazine; vinyl pyrazine; isoquinoline; vinyl isoquinoline; quinoxaline; vinyl quinoxaline; biphenyl; 1,2-diphenyl ether; 1,2-diphenylethane; o-terphenyl; N-methylpyrrole; naphthalene; 3,9-divinyl-2,4,8,10-tetraoxaspiro[5.5]undecane; 3,9-divinyl-2,4,8-trioxaspiro[5.5]undecane; 3,9-divinyl-2,4-dioxaspiro[5.5]undecane; 3,9-diethylidene-2,4,8,10-tetraoxaspiro[5.5]undecane; 3,9-diethylidene-2,4,8-trioxaspiro[5.5]undecane; 3,9-diethylidene-2,4-dioxaspiro[5.5]undecane; 3,9-dimethylene-2,4,8,10-tetraoxaspiro[5.5]undecane; 3,9-divinyl-1,5,7,11-tetraoxaspiro[5.5]undecane; 3,9-dimethylene-1,5,7,11-tetraoxaspiro[5.5]undecane; or 3,9-diethylidene-1,5,7,11-tetraoxaspiro[5.5]undecane. 18. The electrolyte of claim 17, wherein the redox shuttle comprises 5,7-di-tert-butyl-2,3-dibromo-1,4-benzodioxin; 5,7-di-tert-butyl-1,4-benzodioxin; or 4,6-di-tert-butyl-1,3-benzodioxole.
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