Ionic polyesters, polyethers, poly(ether sulfones), and related materials

1. An ionic polymer having the formula:

wherein L 1 and L 2 are independently selected from a chemical bond, C 1-4 alkyl, O, or S;

X 1 and X 2 are independently selected from O and S;

Z is selected from C(O), S(O), SO 2 , or P(O)(OR p ), wherein R p is selected from hydrogen, C 1-8 alkyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, and C 1-8 heterocyclyl;

Cy 1 , Cy 2 , Cy 3 , and Cy 4 are independently selected from aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;

Q 1 and Q 2 are independently selected from C 1-8 alkyl, C 2-8 alkyl, C 2-8 alkyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl; wherein each of Q 1 and Q 2 comprise at least one cationic Group 15 atom that is not bonded to a hydrogen atom;

L 3 is a linker group; and

each A comprises at least one anionic group, and m is a integer such that the polymer is electrically balanced.

2. The polymer of claim 1 , wherein Q 1 and Q 2 independently comprise a group having the formula:

wherein each R is independently selected from C 1-8 alkyl, C 2-8 alkyl, C 2-8 alkyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl, and two or more R groups may together form a ring.

3. The polymer of claim 1 , wherein Q 1 comprises a group having the formula:

wherein R Q1a and R Q1b are independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;

R Q1c and R Q1d are independently selected from null, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;

wherein any two or more of R Q1a , R Q1b , R Q1c , and R Q1d may together form a ring.

4. The polymer of claim 1 , wherein Q 2 comprises a group having the formula:

wherein R Q2a and R Q2b are independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;

R Q2c and R Q2d are independently selected from null, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;

wherein any two or more of R Q2a , R Q2b , R Q2c , and R Q2d may together form a ring.

5. The polymer of claim 1 , wherein Q 1 and Q 2 independently comprise a cationic heterocyclic selected from the group consisting of pyrazolium, pyridinium, pyrazinium, pyrimidinium, pryidazinium, piperidinium, pyrrolidinium, indolizinium, isoindolium, indolium, indazolium, imidazolium, oxazolium, triazolium, tetrazolium, thiazolium, purinium, isoquinolinium, quinolinium, phthalazinium, quinooxalinium, phenazinium, morpholininium, and mixtures thereof.

6. The polymer of claim 1 , wherein Q 1 comprises a cationic heterocycle having the formula:

wherein

each R is independently selected from L 1 , L 3 , F, Cl, Br, I, NO 2 , CN, R a , OR a , N(R a ) 2 , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;

each R 1 is independently selected from L 1 , L 3 , R a′ , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl, and R a′ is in each case independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl,

each R 1a is selected from null, L 1 , L 3 , R a′ , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl; R a′ is in each case independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl,

wherein any two or more R, R 1 and R 1a groups may together form a ring, and

wherein no Q 1 group contains more than one R 1a , L 1 and L 3 groups.

7. The polymer of claim 1 , wherein Q 2 comprises a cationic heterocycle having the formula:

wherein each R is independently selected from L 2 , L 3 , F, Cl, Br, I, NO 2 , CN, R a , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;

each R 1 is independently selected from L 2 , L 3 , R a′ , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl; and R a′ is in each case independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl,

each R 1a is either absent or independently selected from L 2 , L 3 , R a′ , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl;

R a′ is in each case independently selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl,

wherein any two or more R, R 1 and R 1a groups may together form a ring, and

wherein no Q 2 group contains more than one R 1a , L 2 and L 3 groups.

8. The polymer of claim 1 , wherein Q 1 is

wherein R is in each case independently selected from F, Cl, Br, I, NO 2 , CN, R a , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl, wherein any two or more R groups may together form a ring.

9. The polymer of claim 1 , wherein Q 2 is

wherein R is in each case independently selected from F, Cl, Br, I, NO 2 , CN, R a , OR a , N(R a ) 2 , SR a , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl, wherein any two or more R groups may together form a ring.

10. The polymer of claim 1 , wherein L 3 has the formula:

wherein Y 1 and Y 2 are independently selected from null, O, S, and —X 3 —(CH 2 ) n —X 4 —, wherein X 3 and X 4 are independently selected from null, O, and S, and n is an integer from 0-10; and

L 3a is selected from C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl.

11. The polymer of claim 1 , wherein L 3 has the formula:

wherein Y 1 and Y 2 are independently selected from null, O, S, and —X 3 —(CH 2 ) n —X 4 —, wherein X 3 and X 4 are independently selected from null, O and S, and n is an integer from 0-10; and

R L is independently selected from F, Cl, Br, I, NO 2 , CN, R aL , OR aL , N(R aL ) 2 , SR aL , SO 2 R aL , SO 2 N(R aL ) 2 , C(O)R aL ; C(O)OR aL , OC(O)R aL ; C(O)N(R aL ) 2 , N(R aL )C(O)R aL , OC(O)N(R aL ) 2 , N(R aL )C(O)N(R aL ) 2 , wherein R aL is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl, wherein any two or more R L groups may together form a ring.

12. The polymer of claim 11 , wherein Y 1 is para to Y 2 .

13. The polymer of claim 11 , wherein R L is in each case hydrogen.

14. The polymer of claim 11 , wherein Y 1 and Y 2 are each —X 3 —(CH 2 )—X 4 —, wherein X 3 and X 4 are independently selected from null, O and S.

15. The polymer of claim 14 , wherein X 3 and X 4 are in each case null.

16. The polymer of claim 1 , wherein L 3 has the structure:

17. The polymer of claim 1 , having the formula:

R 1 , R 2 , R 3 , and R 4 are in each case independently selected from F, Cl, Br, I, NO 2 , CN, R a , OR a , N(R a ) 2 , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl.

18. The polymer of claim 1 , having the formula:

R 1 , R 2 , R 3 , and R 4 are in each case independently selected from F, Cl, Br, I, NO 2 , CN, R a , OR a , N(R a ) 2 , SO 2 R a , SO 2 N(R a ) 2 , C(O)R a ; C(O)OR a , OC(O)R a ; C(O)N(R a ) 2 , N(R a )C(O)R a , OC(O)N(R a ) 2 , N(R a )C(O)N(R a ) 2 , wherein R a is in each case independently selected from hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, aryl, C 1-8 heteroaryl, C 3-8 cycloalkyl, or C 1-8 heterocyclyl.

19. The polymer of claim 18 , wherein R 1 , R 2 , R 3 , and R 4 are each hydrogen.

20. The polymer of claim 1 , wherein A is chloride, bromide, iodide, nitrate, dicyanamide, acetate, trifluoroacetate, tartrate, succinate, fumarate, citrate, bis(trifluoromethane)sulfonamide, bis(trifluoromethylsulfonyl)imidate, hexafluorophosphate, tetrafluoroborate, sulfate, ethylsulfate, formate, phosphate, tris(perfluoroalkyl)trifluorophosphatemesylate, aluminum chloride, thiocyanide, mesylate, triflate, glycinate, alanate, methioninate, prolinate, taurine, lactate, benzoate, pivalate, or tosylate.