High stability polyionic liquid salts

1. A triionic liquid salt comprising a triionic species, wherein the triionic species corresponds in structure to:

and at least one counterion;

wherein each R, R 1 , R 2 , R 3 and R n are independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, carbocyclyl, heterocyclyl, halo, alkoxy and hydroxy;

and each R c is independently selected from the group consisting of alkyl, cycloalkyl, phenyl, halo, alkoxy and hydroxyl.

2. The triionic liquid salt of claim 1 , wherein the at least one counterion is selected from the group consisting of halogen, BF 4 − , PF 6 − , NTf 2 − , TfO − ,

wherein R is selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, carbocyclyl, heterocyclyl, halo, alkoxy, hydroxyl, alkylcarbonyl, alkylcarbonylalkylene, hydroxycarbonyl,

wherein

X 1 is C 1 -C 10 -alkylene;

X 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino and hydroxy;

Y 1 is selected from the group consisting of hydrogen and alkyl; and

Y 2 is C 1 -C 10 -alkylene.

3. A tetraionic liquid salt comprising a tetraionic species that corresponds in structure to:

wherein Rc is a substituent independently selected from the group consisting of alkyl, cycloalkyl, phenyl, halo, alkoxy and hydroxyl;

each A is an independently selected monoionic group, wherein:

the monoionic group is selected from the group consisting of alkylene, alkenylene, alkynylene, (—CH 2 -carbocyclyl-CH 2 —) n , and polysiloxyl; wherein alkylene, alkenylene, and alkynylene optionally contain one or more heteroatoms selected from the group consisting of O, N, S and Si;

wherein the monoionic group is substituted with a cationic group selected from the group consisting of heterocyclyl, ammonium and phosphonium; wherein the cationic group optionally is substituted with one or more substituents independently selected from the group consisting of alkyl, cycloalkyl, phenyl, halo, alkoxy and hydroxyl; wherein the alkyl optionally is substituted with one or more substituents selected from the group consisting of hydroxy and phenyl; or

the monoionic group is an anionic group selected from the group of substituents consisting of carboxylate, sulfonate and sulfate; wherein each such substituent is optionally substituted with one or more substituents independently selected from the group consisting of alkyl, carbocyclyl and heterocyclyl;

n is selected from the group consisting of 1 to 20, inclusive; and

wherein z is selected from the group consisting of 1 to 20, inclusive.

4. The tetraionic liquid salt of claim 3 , wherein the polyionic species corresponds in structure to:

wherein each R A is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, phenyl, halo, alkoxy and hydroxyl;

wherein z is selected from the group consisting of 1 to 20, inclusive.

5. The tetraionic liquid salt of claim 4 , wherein the at least one counterion is selected from the group consisting of halogen, BF 4 − , PF 6 − , NTf 2 − , TfO − ,

wherein R is selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, carbocyclyl, heterocyclyl, halo, alkoxy, hydroxyl, alkylcarbonyl, alkylcarbonylalkylene, hydroxycarbonyl,

wherein

X 1 is C 1 -C 10 -alkylene;

X 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino and hydroxy;

Y 1 is selected from the group consisting of hydrogen and alkyl; and

Y 2 is C 1 -C 10 -alkylene.

6. The tetraionic liquid salt of claim 5 , wherein there are at least four counterions.

7. A triionic liquid salt comprising a triionic species, wherein the triionic species corresponds in structure to

and at least one counterion.

8. The triionic liquid salt of claim 7 , wherein the at least one counterion is selected from the group consisting of halogen, BF 4 − , PF 6 − , NTf 2 − , TfO − ,

wherein R is selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, carbocyclyl, heterocyclyl, halo, alkoxy, hydroxyl, alkylcarbonyl, alkylcarbonylalkylene, hydroxycarbonyl,

wherein

X 1 is C 1 -C 10 -alkylene;

X 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino and hydroxy;

Y 1 is selected from the group consisting of hydrogen and alkyl; and

Y 2 is C 1 -C 10 -alkylene.

9. A triionic liquid salt comprising a triionic species which corresponds in structure to:

and at least one counterion;

wherein each t is independently selected from the group consisting of 1 to 20, inclusive; wherein

each A is an independently selected monoionic group, wherein:

the monoionic group is selected from the group consisting of alkylene, alkenylene, alkynylene, (—CH 2 -carbocyclyl-CH 2 —) n , and polysiloxyl; wherein alkylene, alkenylene, and alkynylene optionally contain one or more heteroatoms selected from the group consisting of O, N, S and Si;

wherein the monoionic group is substituted with a cationic group selected from the group consisting of heterocyclyl, ammonium and phosphonium; wherein the cationic group optionally is substituted with one or more substituents independently selected from the group consisting of alkyl, carbocyclyl, heterocyclyl, halo, alkoxy and hydroxyl;

wherein the alkyl optionally is substituted with one or more substituents selected from the group consisting of hydroxy and phenyl.

10. The triionic liquid salt of claim 9 , wherein the triionic species corresponds in structure to a formula selected from the group consisting of:

11. The triionic liquid salt of claim 10 , wherein the at least one counterion is selected from the group consisting of halogen, BF 4 − , PF 6 − , NTf 2 − , TfO − ,

wherein R is selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, carbocyclyl, heterocyclyl, halo, alkoxy, hydroxyl, alkylcarbonyl, alkylcarbonylalkylene, hydroxycarbonyl,

wherein

X 1 is C 1 -C 10 -alkylene;

X 2 is selected from the group consisting of hydrogen, alkyl, alkoxy, amino and hydroxy;

Y 1 is selected from the group consisting of hydrogen and alkyl; and

Y 2 is C 1 -C 10 -alkylene.

12. The triionic liquid salt of claim 10 , wherein t is 5.