Semi-interpenetrating and crosslinked polymers and membranes thereof

1. A composition comprising a structure of the formula:

or a salt thereof, wherein:

each of P1, P2, and P3 is independently a structure of any one or more of the following:

wherein each of R 7 and R 8 is, independently, an electron-withdrawing moiety, H, optionally substituted aliphatic, optionally substituted alkyl, optionally substituted heteroaliphatic, optionally substituted heteroalkyl, optionally substituted aromatic, optionally substituted aryl, or optionally substituted arylalkylene, wherein R 7 and R 8 can be taken together to form an optionally substituted cyclic group;

each of R 9 and R 10 is, independently, H, optionally substituted aliphatic, optionally substituted alkyl, optionally substituted heteroaliphatic, optionally substituted heteroalkyl, optionally substituted aromatic, optionally substituted aryl, or optionally substituted arylalkylene, or wherein R 9 and R 10 can be taken together to form an optionally substituted cyclic group;

n is an integer of 1 or more;

each of ring a, ring b, and/or ring c can be optionally substituted; and

Z is a core moiety;

and

at least one of Z, P1, P2 or P3 comprises an ionizable moiety or an ionic moiety.

2. The composition of claim 1 , wherein one or more of ring a, ring b, ring c, R 7 , R 8 , R 9 , and R 10 can, independently, optionally comprise an ionizable moiety or an ionic moiety.

3. The composition of claim 1 , wherein Z comprises a structure of formula (IIa) or (IIb):

Z 1 is a multivalent moiety;

each of Ar 1 , Ar 2 , Ar 3 , and Ar 4 comprises, independently, an optionally substituted aromatic or optionally substituted arylene; and

each of L 1 , L 2 , L 3 , L 4 , L a , L b , L c , and L d is, independently, a covalent bond, —O—, —NR N1 —, —C(O)—, optionally substituted aliphatic, optionally substituted alkylene, optionally substituted heteroaliphatic, or optionally substituted heteroalkylene,

wherein R N1 is H, optionally substituted aliphatic, optionally substituted alkyl, optionally substituted aromatic, or optionally substituted aryl, and

wherein each of L 1 , L 2 , L 3 , L 4 , L a , L b , L c , and L d can, independently, optionally comprise an ionizable moiety or an ionic moiety.

4. The composition of claim 3 , wherein each of Ar 1 , Ar 2 , Ar 3 , and Ar 4 is, independently, -L-Ar—, -L-Ar-L-, -Ar-L-, -L-Ar—Ar-L-, -L-Ar—Ar-Ar-L-, or —Ar-L-Ar—; wherein each Ar is, independently, an optionally substituted aromatic or optionally substituted arylene; and wherein each L is, independently, a covalent bond, —O—, —NR N1 —, —C(O)—, optionally substituted aliphatic, optionally substituted alkylene, optionally substituted alkyleneoxy, optionally substituted heteroaliphatic, or optionally substituted heteroalkylene.

5. The composition of claim 1 , wherein each P1, P2, and P3 comprises, independently, a structure of the formula:

wherein:

each of R 7 and R 8 is, independently, an electron-withdrawing moiety, H, optionally substituted aliphatic, optionally substituted alkyl, optionally substituted heteroaliphatic, optionally substituted heteroalkyl, optionally substituted aromatic, optionally substituted aryl, or optionally substituted arylalkylene, wherein R 7 and R 8 can be taken together to form an optionally substituted cyclic group;

n is an integer of 1 or more;

each of ring a, ring b, and/or ring c can be optionally substituted; and

wherein one or more of ring a, ring b, ring c, R 7 , and R 8 can, independently, optionally comprise an ionizable moiety or an ionic moiety.

6. The composition of claim 5 , wherein the electron-withdrawing moiety is an optionally substituted haloalkyl, cyano, phosphate, sulfate, sulfonic acid, sulfonyl, difluoroboranyl, borono, thiocyanato, or piperidinium.

7. The composition of claim 5 , wherein the ionizable moiety or the ionic moiety comprises -L A -X A or -L A -(L A′ -X A ) L2 or -L A -(X A -L A′ -X A′ ) L2 or -L A -X A -L A′ -X A′ or -L A -X A -L A′ -X A′ -L A″ -X A″ , wherein:

each L A , L A′ , and L A″ is a linking moiety;

each X A , X A′ , and X A″ comprises, independently, an acidic moiety, a basic moiety, or a multi-ionic moiety; and

L2 is an integer of 1 or more.

8. The composition of claim 7 , wherein each L A , L A′ , and L A″ comprises, independently, an optionally substituted alkylene, optionally substituted alkyleneoxy, optionally substituted heteroalkylene, optionally substituted arylene, and/or optionally substituted aryleneoxy.

9. The composition of claim 7 , wherein each X A , X A′ , and X A″ comprises, independently, sulfo, sulfonate anion, sulfonium cation, carboxy, carboxylate anion, phosphono, phosphonate anion, phosphonium cation, phosphazenium cation, amino, ammonium cation, heterocyclic cation, piperidinium cation, azepanium cation, or a salt form thereof.

10. The composition of claim 1 , wherein the optionally substituted rings a-c are substituted with one or more substituents; and wherein the substituent is selected from the group consisting of alkyl, alkoxy, alkoxyalkyl, amino, aminoalkyl, aryl, arylalkylene, aryloyl, aryloxy, arylalkoxy, cyano, hydroxy, hydroxyalkyl, nitro, halo, and haloalkyl.

11. The composition of claim 1 , wherein the composition comprises a polymer or a copolymer.

12. The composition of claim 1 , wherein the composition comprises a film, a membrane, or a cross-linked polymeric matrix.

13. An electrochemical cell comprising:

an anode;

a cathode; and

a polymer electrolyte membrane disposed between the anode and the cathode, wherein the polymer electrolyte membrane comprises a composition of claim 1 .

14. A method of making a polymer, the method comprising:

providing one or more polymeric units in the presence of an interpenetrating agent and a Friedel-Crafts alkylation agent, wherein the interpenetrating agent comprises a core moiety Z and the Friedel-Crafts alkylation agent comprises a haloalkyl group and a reactive group, thereby forming an initial polymer having a reactive group; and

substituting the reactive group with an ionic moiety, thereby providing an ionic polymer, wherein the ionic polymer comprises a composition of claim 1 .