VISCOSITY REDUCTION FOR IONIC LIQUID ELECTROLYTES

1 . An energy storage device comprising:

an anode including a plurality of active material particles, each of the plurality of active material particles having a particle size of between about 1 nanometer and about fifty micrometers, wherein one or more of the plurality of active material particles are enclosed by and in contact with a membrane coating permeable to lithium ions, the membrane coating a thermoplastic polymer treated to a cyclized, non-plastic ladder compound;

a cathode; and

an electrolyte coupling the anode to the cathode including a room temperature ionic liquid solvent and at least one wetting agent or viscosity reducing co-solvent and mixtures thereof.

2 . The energy storage device of claim 1 , wherein the anode comprises a plurality of active material particles comprising a plurality of silicon particles.

3 . The energy storage device of claim 1 , wherein the electrolyte comprises at least one of a bisfluorosulfonylimide solvent anion and a lithium bisfluorosulfonylimide salt.

4 . The energy storage device of claim 1 , wherein the viscosity reducing solvent comprises a functionalized pyrrolidinum cation.

5 . The energy storage device of claim 4 , wherein one or more of the atoms in the heterocyclic ring of the pyrrolidinium cation is substituted with one or more moieties selected from the group consisting of halides, oxygen, nitrogen, sulfur, phosphorus, alkanes, esters, ethers, ketones, carbonyls, alkoxyalkanes, alkenes, alkynes, aryls, nitriles, silanes, sulfones, thiols, phenols, hydroxyls, amines, imides, aldehydes, carboxylic acids, carbonates, and acid anhydrides; and

wherein any of the carbon or hydrogen atoms in the above moieties are further substituted with halides, oxygen, nitrogen, sulfur, phosphorus, alkanes, esters, ethers, ketones, carbonyls, alkoxyalkanes, alkenes, alkynes, aryls, nitriles, silanes, sulfones, thiols, phenols, hydroxyls, amines, imides, aldehydes, carboxylic acids, carbonates, and acid anhydrides.

6 . The energy storage device of claim 1 , wherein the viscosity reducing solvent comprises a silane or siloxane solvent.

7 . The energy storage device of claim 6 , wherein the silane or siloxane solvent comprises at least one of phenyltrimethoxysilane, ethyltrimethoxysilane, pentafluorophenyltrimethoxylsilane, and phenethyltris(trimethylsiloxy)silane, Tris(pentafluorophenyl)silane, tris(trimethylsilyl)phosphate, tris(trimethylsilyl)phosphite, tris(trimethylsilyl)borate, bis(methoxytriethyleneoxypropyl)-tetra methyldisiloxane, silanes of the formulae:

(CH 3 ) 3 SiO(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 SiO(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 SiO(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 SiO(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 3 SiO(CH 2 CH 2 O) 6 CH 3 , (CH 3 ) 3 SiO(CH 2 CH 2 O) 7 CH 3 ; (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 6 CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 7 CH 3 , (CH 3 ) 3 Si(CH 2 ) 3 O(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 Si(CH 2 ) 3 O(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 Si(CH 2 ) 3 O(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 Si(CH 2 ) 3 O(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 2 Si[O(CH 2 CH 2 O) 2 CH 3 ] 2 , (CH 3 ) 2 Si[O(CH 2 CH 2 O) 3 CH 3 ] 2 , (CH 3 ) 2 Si[O(CH 2 CH 2 O) 4 CH 3 ] 2 , (CH 3 ) 2 Si[O(CH 2 CH 2 O) 5 CH 3 ] 2 ; CH 3 Si[O(CH 2 CH 2 O) 2 CH 3 ] 3 , CH 3 Si[O(CH 2 CH 2 O) 3 CH 3 ] 3 , CH 3 Si[O(CH 2 CH 2 O) 4 CH 3 ] 3 ; Si[O(CH 2 CH 2 O) 2 CH 3 ] 4 , Si[O(CH 2 CH 2 O) 3 CH 3 ] 4 ; (CH 3 ) 2 Si[O(CH 2 CH 2 O) 2 CH 3 ][(CH 2 ) 3 0 (CH 2 CH 2 O) 2 CH 3 ], (CH 3 ) 2 Si[O(CH 2 CH 2 O) 3 CH 3 ][(CH 2 ) 3 O(CH 2 CH 2 O) 3 CH 3 ], (CH 3 ) 2 Si[O(CH 2 CH 2 O) 4 CH 3 ][(CH 2 ) 3 O(CH 2 CH 2 O) 4 CH 3 ], (CH 3 ) 2 Si[O(CH 2 CH 2 O) 5 CH 3 ][(CH 2 ) 3 O(CH 2 CH 2 O) 5 CH 3 ],

and siloxanes of the formulae:

(CH 3 ) 3 SiO(CH 2 CH 2 O) n CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) n CH 3 ; (CH 3 ) 3 Si(CH 2 ) 3 O(CH 2 CH 2 O) n′ CH 3 ; (CH 3 ) 2 Si[O(CH 2 CH 2 O) n′ CH 3 ] 2 ; CH 3 Si[O(CH 2 CH 2 O) p CH 3 ] 3 , Si[O(CH 2 CH 2 O) p CH 3 ] 4 ; (CH 3 ) 2 Si[O(CH 2 CH 2 O) n′ CH 3 ][(CH 2 ) 3 O(CH 2 CH 2 O) n′ CH 3 ]; (CH 3 ) 3 SiOR; (CH 3 ) 3 Si(CH 2 ) 3 OR; CH 3 O(CH 2 CH 2 O) n Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) n CH 3 , CH 3 O(CH 2 CH 2 O) n CH 2 Si(CH 3 ) 2 O(CH 3 ) 2 SiCH 2 O(CH 2 CH 2 O) n CH 3 , CH 3 O(CH 2 CH 2 O) n (CH 2 ) 3 Si(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 2 CH 2 O) n CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si(CH 2 ) 3 O(CH 2 CH 2 O) n CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si(CH 2 ) 2 O(CH 2 CH 2 O) n CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) n CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiOR; ROSi(CH 3 ) 2 O(CH 3 ) 2 SiO—R; (CH 3 ) 3 SiO(CH 3 ) 2 Si(CH 2 ) 3 OR; RO(CH 2 ) 3 Si(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 OR; CH 3 O(CH 2 CH 2 O) n Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) n CH 3 , CH 3 O(CH 2 CH 2 O) n′ (CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 3 ) 2 Si—(OCH 2 CH 2 ) n′ OCH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) n CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) n CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) n (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , ROSi(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiOR, ROSi(CH 3 ) 2 OSi(CH 3 ) 2 OSi(CH 3 ) 3 , RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 OR, RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 OSi(CH 3 ) 3 ; ROSi(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 ) n CH 3 , or RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 2 CH 2 ) n CH 3 , CH 3 O(CH 2 CH 2 O) 2 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 2 CH 3 , CH 3 O(CH 2 CH 2 O) 3 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O)3CH 3 , CH3O(CH 2 CH 2 O) 4 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 4 CH 3 , CH 3 O(CH 2 CH 2 O) 5 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 5 CH 3 , CH 3 O(CH 2 CH 2 O) 6 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 6 CH 3 , CH 3 O(CH 2 CH 2 O) 7 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 7 CH 3 ; CH 3 O(CH 2 CH 2 O) 2 CH 2 —Si(CH 3 ) 2 O(CH 3 ) 2 Si—CH 2 O(CH 2 CH 2 O) 2 CH 3 , CH 3 O(CH 2 CH 2 O) 2 CH 2 Si(CH 3 ) 3 O(CH 3 ) 2 Si—CH 2 O(CH 2 CH 2 O) 3 CH 3 , CH 3 O(CH 2 CH 2 O) 4 CH 2 Si(CH 3 ) 2 O(CH 3 ) 2 SiCH 2 O(CH 2 CH 2 O) 4 CH 3 , CH 3 O(CH 2 CH 2 O) 5 CH 2 Si(CH 3 ) 2 O(CH 3 ) 2 SiCH 2 O(CH 2 CH 2 O) 5 CH 3 , CH 3 O(CH 2 CH 2 O) 6 CH 2 —Si(CH 3 ) 2 O(CH 3 ) 2 SiCH 2 O(CH 2 CH 2 O) 6 CH 3 , CH 3 O(CH 2 CH 2 O) 7 CH 2 Si(CH 3 ) 2 O(CH 3 ) 2 Si—CH 2 O(CH 2 CH 2 O) 7 CH 3 , CH 3 O(CH 2 CH 2 O) 2 (CH 2 ) 3 Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 2 CH 3 , CH 3 O(CH 2 CH 2 O) 3 (CH 2 ) 3 —Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 3 CH 3 , CH 3 O(CH 2 CH 2 O) 4 (CH 2 ) 3 —Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 4 CH 3 , CH 3 O(CH 2 CH 2 O) 5 (CH 2 ) 3 —Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 5 CH 3 , CH 3 O(CH 2 CH 2 O) 6 (CH 2 ) 3 —Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 6 CH 3 , CH 3 O(CH 2 CH 2 O) 7 (CH 2 ) 3 Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 7 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 6 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 7 CH 3 ; (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 6 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 7 CH 3 ; (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 6 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 7 CH 3 , CH 3 O(CH 2 CH 2 O) 2 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 2 CH 3 , CH 3 O(CH 2 CH 2 O) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 3 CH 3 , CH 3 O(CH 2 CH 2 O) 4 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 4 CH 3 , CH 3 O(CH 2 CH 2 O) 5 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 5 CH 3 , CH 3 O(CH 2 CH 2 O) 6 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 6 CH 3 , CH 3 O(CH 2 CH 2 O) 7 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 7 CH 3 ; CH 3 O(CH 2 CH 2 O) 2 (CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 2 CH 3 , CH 3 O(CH 2 CH 2 O) 3 (CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 3 CH 3 , CH 3 O(CH 2 CH 2 O) 4 (CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 4 CH 3 , CH 3 O(CH 2 CH 2 O) 5 (CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 5 CH 3 ; [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 2 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 3 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 4 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 5 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 6 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 7 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 2 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 3 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 4 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 5 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 6 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 7 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 2 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 3 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 4 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 5 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 6 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 7 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , R—OSi(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO—R, R—OSi(CH 3 ) 2 OSi(CH 3 ) 2 OSi(CH 3 ) 3 , RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 —OR, RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 OSi(CH 3 ) 3 , R—OSi(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 ) n CH 3 , or RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 2 CH 2 ) n CH 3 , wherein

R is a carbonate group; n is 2, 3, 4, 5, 6, or 7;

n′ is 2, 3, 4, or 5;

p is 2, 3, or 4; and

p′ is 2 or 3.

8 . The energy storage device of claim 1 , wherein the viscosity reducing solvent comprises a fluorinated ether solvent.

9 . The energy storage device of claim 8 , wherein the fluorinated alkyl ether solvent comprises at least one of 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetrafluoropropyl ether, 1,1,2,3,3,3-hexafluoropropyl-2,2,3,3-tetrafluoropropyl ether, 2,2,3,3,3-pentafluoropropyl-1,1,2,2-tetrafluoroethyl ether, 1,1,2,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetrafluoropropyl ether, methyl ether, tetrafluoropropyl-propylene carbonate-ether, 1,1,2,2-tetrafluoroethyl ethyl ether, 2-methyl tetrahydrofuran, 1,3-dioxolane, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethane, 1,2-dibutoxyethane, methyl nonafluorobutyl ether, ethyl nonafluorobutyl ether, bis(2,2,2-trifluoroethyl) ether, 2-trifluoromethyl hexafluoropropyl methyl ether, 2-trifluoromethyl hexafluoropropyl ethyl ether, 2-trifluoromethyl hexafluoropropyl propyl ether, 3-trifluoro octafluorobutyl methyl ether, 3-trifluoro octafluorobutyl ethyl ether, 3-trifluoro octafluorobutyl propyl ether, 4-trifluorodecafluoropenthyl methyl ether, 4-trifluorodecafluoropenthyl ethyl ether, 4-trifluorodecafluoropenthyl propyl ether, 5-trifluorododecafluorohexyl methyl ether, 5-trifluorododecafluorohexyl ethyl ether, 5-trifluorododecafluorohexyl propyl ether, 6-trifluorotetradecafluoroheptyl methyl ether, 6-trifluorotetradecafluoroheptyl ethyl ether, 6-trifluorotetradecafluoroheptyl propyl ether, 7-trifluorohexadecafluorooctyl methyl ether, 7-trifluorohexadecafluorooctyl ethyl ether, and 7-trifluorohexadecafluorohexyl octyl ether, dimethoxy methane, 1,2-dimethoxy ethane, digryme, trigryme, 1,3-dioxolane, and tetrahydrofuran.

10 . An electrolyte composition suitable for use in an energy storage device comprising an anode and a cathode, the electrolyte composition comprising:

a room temperature ionic liquid solvent and at least one wetting agent or viscosity reducing co-solvent and mixtures thereof.

11 . The energy storage device of claim 10 , wherein the viscosity reducing solvent comprises a functionalized pyrrolidinum cation.

12 . The energy storage device of claim 11 , wherein one or more of the atoms in the heterocyclic ring of the pyrrolidinium cation is substituted with one or more moieties selected from the group consisting of halides, oxygen, nitrogen, sulfur, phosphorus, alkanes, esters, ethers, ketones, carbonyls, alkoxyalkanes, alkenes, alkynes, aryls, nitriles, silanes, sulfones, thiols, phenols, hydroxyls, amines, imides, aldehydes, carboxylic acids, carbonates, and acid anhydrides; and

wherein any of the carbon or hydrogen atoms in the above moieties are further substituted with halides, oxygen, nitrogen, sulfur, phosphorus, alkanes, esters, ethers, ketones, carbonyls, alkoxyalkanes, alkenes, alkynes, aryls, nitriles, silanes, sulfones, thiols, phenols, hydroxyls, amines, imides, aldehydes, carboxylic acids, carbonates, and acid anhydrides.

13 . The energy storage device of claim 10 , wherein the viscosity reducing solvent comprises a silane or siloxane solvent.

14 . The energy storage device of claim 13 , wherein the silane or siloxane solvent comprises at least one of phenyltrimethoxysilane, ethyltrimethoxysilane, pentafluorophenyltrimethoxylsilane, and phenethyltris(trimethylsiloxy)silane, Tris(pentafluorophenyl)silane, tris(trimethylsilyl)phosphate, tris(trimethylsilyl)phosphite, tris(trimethylsilyl)borate, bis(methoxytriethyleneoxypropyl)-tetramethyldisiloxane, silanes the of the formulae:

(CH 3 ) 3 SiO(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 SiO(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 SiO(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 SiO(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 3 SiO(CH 2 CH 2 O) 6 CH 3 , (CH 3 ) 3 SiO(CH 2 CH 2 O) 7 CH 3 ; (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 6 CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) 7 CH 3 ; (CH 3 ) 3 Si(CH 2 ) 3 O(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 Si(CH 2 ) 3 O(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 Si(CH 2 ) 3 O(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 Si(CH 2 ) 3 O(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 2 Si[O(CH 2 CH 2 O) 2 CH 3 ] 2 , (CH 3 ) 2 Si[O(CH 2 CH 2 O) 3 CH 3 ] 2 , (CH 3 ) 2 Si[O(CH 2 CH 2 O) 4 CH 3 ] 2 , (CH 3 ) 2 Si[O(CH 2 CH 2 O) 5 CH 3 ] 2 ; CH 3 Si[O(CH 2 CH 2 O) 2 CH 3 ] 3 , CH 3 Si[O(CH 2 CH 2 O) 3 CH 3 ] 3 , CH 3 Si[O(CH 2 CH 2 O) 4 CH 3 ] 3 ; Si[O(CH 2 CH 2 O) 2 CH 3 ] 4 , Si[O(CH 2 CH 2 O) 3 CH 3 ] 4 , (CH 3 ) 2 Si[O(CH 2 CH 2 O) 2 CH 3 ][(CH 2 ) 3 0 (CH 2 CH 2 O) 2 CH 3 ], (CH 3 ) 2 Si[O(CH 2 CH 2 O) 3 CH 3 ][(CH 2 ) 3 O(CH 2 CH 2 O) 3 CH 3 ], (CH 3 ) 2 Si[O(CH 2 CH 2 O) 4 CH 3 ][(CH 2 ) 3 O(CH 2 CH 2 O) 4 CH 3 ], (CH 3 ) 2 Si[O(CH 2 CH 2 O) 5 CH 3 ][(CH 2 ) 3 O(CH 2 CH 2 O) 5 CH 3 ],

and siloxanes of the formulae:

(CH 3 ) 3 SiO(CH 2 CH 2 O) n CH 3 , (CH 3 ) 3 SiCH 2 O(CH 2 CH 2 O) n CH 3 ; (CH 3 ) 3 Si(CH 2 ) 3 O(CH 2 CH 2 O) n′ CH 3 ; (CH 3 ) 2 Si[O(CH 2 CH 2 O) n′ CH 3 ] 2 ; CH 3 Si[O(CH 2 CH 2 O) p CH 3 ] 3 , Si[O(CH 2 CH 2 O) p CH 3 ] 4 ; (CH 3 ) 2 Si[O(CH 2 CH 2 O) n′ CH 3 ][(CH 2 ) 3 O(CH 2 CH 2 O) n′ CH 3 ]; (CH 3 ) 3 SiOR; (CH 3 ) 3 Si(CH 2 ) 3 OR; CH 3 O(CH 2 CH 2 O) n Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) n CH 3 , CH 3 O(CH 2 CH 2 O) n CH 2 Si(CH 3 ) 2 O(CH 3 ) 2 SiCH 2 O(CH 2 CH 2 O) n CH 3 , CH 3 O(CH 2 CH 2 O) n (CH 2 ) 3 Si(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 2 CH 2 O) n CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si(CH 2 ) 3 O(CH 2 CH 2 O) n CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si(CH 2 ) 2 O(CH 2 CH 2 O) n CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) n CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiOR; ROSi(CH 3 ) 2 O(CH 3 ) 2 SiO—R; (CH 3 ) 3 SiO(CH 3 ) 2 Si(CH 2 ) 3 OR; RO(CH 2 ) 3 Si(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 OR; CH 3 O(CH 2 CH 2 O) n Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) n CH 3 , CH 3 O(CH 2 CH 2 O) n′ (CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 3 ) 2 Si—(OCH 2 CH 2 ) n′ OCH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) n CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) n CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) n (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , ROSi(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiOR, ROSi(CH 3 ) 2 OSi(CH 3 ) 2 OSi(CH 3 ) 3 , RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 OR, RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 OSi(CH 3 ) 3 ; ROSi(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 ) n CH 3 , or RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 2 CH 2 ) n CH 3 , CH 3 O(CH 2 CH 2 O) 2 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 2 CH 3 , CH 3 O(CH 2 CH 2 O) 3 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O)3CH 3 , CH3O(CH 2 CH 2 O) 4 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 4 CH 3 , CH 3 O(CH 2 CH 2 O) 5 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 5 CH 3 , CH 3 O(CH 2 CH 2 O) 6 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 6 CH 3 , CH 3 O(CH 2 CH 2 O) 7 Si(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 7 CH 3 ; CH 3 O(CH 2 CH 2 O) 2 CH 2 —Si(CH 3 ) 2 O(CH 3 ) 2 Si—CH 2 O(CH 2 CH 2 O) 2 CH 3 , CH 3 O(CH 2 CH 2 O) 2 CH 2 Si(CH 3 ) 3 O(CH 3 ) 2 Si—CH 2 O(CH 2 CH 2 O) 3 CH 3 , CH 3 O(CH 2 CH 2 O) 4 CH 2 Si(CH 3 ) 2 O(CH 3 ) 2 SiCH 2 O(CH 2 CH 2 O) 4 CH 3 , CH 3 O(CH 2 CH 2 O) 5 CH 2 Si(CH 3 ) 2 O(CH 3 ) 2 SiCH 2 O(CH 2 CH 2 O) 5 CH 3 , CH 3 O(CH 2 CH 2 O) 6 CH 2 —Si(CH 3 ) 2 O(CH 3 ) 2 SiCH 2 O(CH 2 CH 2 O) 6 CH 3 , CH 3 O(CH 2 CH 2 O) 7 CH 2 Si(CH 3 ) 2 O(CH 3 ) 2 Si—CH 2 O(CH 2 CH 2 O) 7 CH 3 ; CH 3 O(CH 2 CH 2 O) 2 (CH 2 ) 3 Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 2 CH 3 , CH 3 O(CH 2 CH 2 O) 3 (CH 2 ) 3 —Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 3 CH 3 , CH 3 O(CH 2 CH 2 O) 4 (CH 2 ) 3 —Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 4 CH 3 , CH 3 O(CH 2 CH 2 O) 5 (CH 2 ) 3 —Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 5 CH 3 , CH 3 O(CH 2 CH 2 O) 6 (CH 2 ) 3 —Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 6 CH 3 , CH 3 O(CH 2 CH 2 O) 7 (CH 2 ) 3 Si(CH 3 ) 2 O(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 7 CH 3 ; (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 6 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 3 O(CH 2 CH 2 O) 7 CH 3 ; (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 6 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 Si—(CH 2 ) 2 O(CH 2 CH 2 O) 7 CH 3 ; (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 2 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 3 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 4 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 5 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 6 CH 3 , (CH 3 ) 3 SiO(CH 3 ) 2 SiO(CH 2 CH 2 O) 7 CH 3 , CH 3 O(CH 2 CH 2 O) 2 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 2 CH 3 , CH 3 O(CH 2 CH 2 O) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 3 CH 3 , CH 3 O(CH 2 CH 2 O) 4 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 4 CH 3 , CH 3 O(CH 2 CH 2 O) 5 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 5 CH 3 , CH 3 O(CH 2 CH 2 O) 6 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 6 CH 3 , CH 3 O(CH 2 CH 2 O) 7 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 7 CH 3 ; CH 3 O(CH 2 CH 2 O) 2 (CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 2 CH 3 , CH 3 O(CH 2 CH 2 O) 3 (CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 3 CH 3 , CH 3 O(CH 2 CH 2 O) 4 (CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 4 CH 3 , CH 3 O(CH 2 CH 2 O) 5 (CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 3 ) 2 SiO(CH 2 CH 2 O) 5 CH 3 ; [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 2 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 3 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 4 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 5 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 6 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 7 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 2 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 3 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 4 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 5 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 6 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )(CH 2 ) 3 O(CH 2 CH 2 O) 7 CH 3 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 2 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 3 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 4 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 5 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 6 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , [(CH 3 ) 3 SiO] 2 Si(CH 3 )O(CH 2 CH 2 O) 7 (CH 3 )Si[OSi(CH 3 ) 3 ] 2 , R—OSi(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO—R, R—OSi(CH 3 ) 2 OSi(CH 3 ) 2 OSi(CH 3 ) 3 , RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O—R, RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 OSi(CH 3 ) 3 , R—OSi(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 SiO(CH 2 CH 2 ) n CH 3 , or RO(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 O(CH 3 ) 2 Si(CH 2 ) 3 O(CH 2 CH 2 ) n CH 3 , wherein

R is a carbonate group; n is 2, 3, 4, 5, 6, or 7;

n′ is 2, 3, 4, or 5;

p is 2, 3, or 4; and

p′ is 2 or 3.

15 . The energy storage device of claim 10 , wherein the viscosity reducing solvent comprises a fluorinated ether solvent.

16 . The energy storage device of claim 15 , wherein the fluorinated alkyl ether solvent comprises at least one of 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetrafluoropropyl ether, 1,1,2,3,3,3-hexafluoropropyl-2,2,3,3-tetrafluoropropyl ether, 2,2,3,3,3-pentafluoropropyl-1,1,2,2-tetrafluoroethyl ether, 1,1,2,2-tetrafluoroethyl-2,2,2-trifluoroethyl ether, 1,1,2,2-tetrafluoroethyl-2,2,3,3-tetrafluoropropyl ether, methyl ether, tetrafluoropropyl-propylene carbonate-ether, 1,1,2,2-tetrafluoroethyl ethyl ether, 2-methyl tetrahydrofuran, 1,3-dioxolane, 1,4-dioxane, 1,2-dimethoxyethane, 1,2-diethoxyethane, 1,2-dibutoxyethane, methyl nonafluorobutyl ether, ethyl nonafluorobutyl ether, bis(2,2,2-trifluoroethyl) ether, 2-trifluoromethyl hexafluoropropyl methyl ether, 2-trifluoromethyl hexafluoropropyl ethyl ether, 2-trifluoromethyl hexafluoropropyl propyl ether, 3-trifluoro octafluorobutyl methyl ether, 3-trifluoro octafluorobutyl ethyl ether, 3-trifluoro octafluorobutyl propyl ether, 4-trifluorodecafluoropenthyl methyl ether, 4-trifluorodecafluoropenthyl ethyl ether, 4-trifluorodecafluoropenthyl propyl ether, 5-trifluorododecafluorohexyl methyl ether, 5-trifluorododecafluorohexyl ethyl ether, 5-trifluorododecafluorohexyl propyl ether, 6-trifluorotetradecafluoroheptyl methyl ether, 6-trifluorotetradecafluoroheptyl ethyl ether, 6-trifluorotetradecafluoroheptyl propyl ether, 7-trifluorohexadecafluorooctyl methyl ether, 7-trifluorohexadecafluorooctyl ethyl ether, and 7-trifluorohexadecafluorohexyl octyl ether, dimethoxy methane, 1,2-dimethoxy ethane, digryme, trigryme, 1,3-dioxolane, and tetrahydrofuran.