High performance, durable polymers including poly(phenylene)

1. A composition comprising a structure having the formula (I):

or a salt thereof, wherein:

each R 3 is, independently, H, optionally substituted C 1-12 alkyl, optionally substituted C 1-12 haloalkyl, optionally substituted C 1-12 perfluoroalkyl, R S , R P , or R F , wherein R S is an acidic moiety comprising a sulfonyl group, R P is an acidic moiety comprising a phosphoryl group, and R F is an electron-withdrawing moiety selected from the group consisting of optionally substituted aryloyl, carboxyaldehyde, optionally substituted alkanoyl, and optionally substituted alkyl;

each Ar L is, independently, a bivalent linker comprising optionally substituted arylene;

each R 1 is, independently, H, R S , R P , or R F ;

each Ar M is, independently, a bivalent linker comprising optionally substituted arylene;

each q is, independently, an integer of from 1 to 5;

m is an integer of from about 1 to 500; and

wherein at least one R 1 or Ar L in formula (I) comprises R S , R P , or R F .

2. The composition of claim 1 , wherein each and every R 3 is, independently, R S , R P , or R F .

3. The composition of claim 1 , wherein R S is —SO 2 —R S1 or —SO 2 —NR N1 —R S2 or —SO 2 —NR N1 —SO 2 —R S3 , wherein each R S1 is independently, H, optionally substituted alkyl, optionally substituted haloalkyl, optionally substituted perfluoroalkyl, optionally substituted aryl, optionally substituted alkaryl, or hydroxyl; each R N1 is, independently, H or optionally substituted C 1-12 alkyl, optionally substituted aryl, or optionally substituted alkaryl; each R S2 is, independently, H, hydroxyl, optionally substituted alkyl, optionally substituted alkylsulfonyl, optionally substituted aryl, or optionally substituted alkaryl; and each R S3 is, independently, H, hydroxyl, optionally substituted alkyl, optionally substituted C 1-12 haloalkyl, optionally substituted perfluoroalkyl, optionally substituted aryl, or optionally substituted alkaryl.

4. The composition of claim 1 , wherein R P is —P(O)(OH) 2 or —O—PO(OH) 2 or —P(O)<R P1 R P2 or —P(O)<R Ar R P2 or —P(O)<R Ar R Ar , and wherein each of R P1 and R P2 is, independently, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted alkaryl, optionally substituted aryloxy, hydroxyl, or H; and each of R Ar is, independently, optionally substituted aryl, optionally substituted alkaryl, or optionally substituted aryloxy.

5. The composition of claim 1 , wherein each and every R 1 and Ar L in formula (I) comprises R S , R P , or R F .

6. The composition of claim 1 , wherein R F is substituted with perfluoroalkyl.

7. The composition of claim 1 , wherein Ar L is optionally substituted phenylene, optionally substituted naphthylene, or optionally substituted phenanthrylene.

8. The composition of claim 7 , wherein the optional substitution for Ar L is R S , R P , or R F .

9. The composition of claim 1 , wherein Ar M is optionally substituted phenylene, optionally substituted naphthylene, or optionally substituted phenanthrylene.

10. The composition of claim 9 , wherein the optional substitution for Ar M is R S , R P , R F , or a label.

11. The composition of claim 1 , further comprising the structure having the formula (I) covalently bonded to a structure having the formula (III′):

or a salt thereof, by way of a linking segment L,

wherein:

each R S is, independently, an acidic moiety comprising a sulfonyl group;

each R 1 is, independently, H, R S , R P , or R F , wherein R P is an acidic moiety comprising a phosphoryl group and R F is an electron-withdrawing moiety; and

each R 2 is, independently, H, R S , R P , R F , halo, optionally substituted C 1-12 alkyl, optionally substituted C 1-12 haloalkyl, optionally substituted C 1-12 perfluoroalkyl, or a label.

12. A composition comprising a structure having the formula (II):

or a salt thereof, wherein:

each R 3 is, independently, H, optionally substituted C 1-12 alkyl, optionally substituted C 1-12 haloalkyl, optionally substituted C 1-12 perfluoroalkyl, R S , R P , or R F , wherein R S is an acidic moiety comprising a sulfonyl group, R P is an acidic moiety comprising a phosphoryl group, and R F is an electron-withdrawing moiety selected from the group consisting of optionally substituted aryloyl, carboxyaldehyde, optionally substituted alkanoyl, and optionally substituted alkyl;

each Ar L is, independently, a bivalent linker comprising optionally substituted arylene;

each R 1 is, independently, H, R S , R P , or R F ;

each Ar M is, independently, a bivalent linker comprising optionally substituted arylene;

each q is, independently, an integer of from 1 to 5;

each of m and n is, independently, an integer of from about 1 to 500;

L is a linking segment; and

Ar H is a hydrophobic segment, and

wherein at least one R 1 or Ar L in formula (II) comprises R S , R P , or R F .

13. The composition of claim 12 , wherein L comprises a covalent bond, carbonyl, oxy, phosphonoyl, phosphoryl, sulfonyl, sulfinyl, sultam, imino, nitrilo, optionally substituted C 1-12 alkylene, optionally substituted C 1-12 alkyleneoxy, optionally substituted C 1-12 heteroalkylene, optionally substituted C 1-12 heteroalkyleneoxy, optionally substituted C 4-18 arylene, optionally substituted C 4-18 aryleneoxy, optionally substituted polyphenylene, or a structure of formula (I).

14. The composition of claim 12 , wherein Ar H comprises a structure of formula (I), a sulfone subunit, an arylene sulfone subunit, an ether sulfone subunit, an arylene ether subunit, a perfluoroalkyl subunit, or a perfluoroalkoxy subunit.

15. The composition of claim 12 , wherein m is less than n.

16. A composition having the formula (IV):

or a salt thereof, wherein:

each R 3 is, independently, H, R S , R P , or R F , wherein R S is an acidic moiety comprising a sulfonyl group, R P is an acidic moiety comprising a phosphoryl group, and R F is an electron-withdrawing moiety selected from the group consisting of optionally substituted aryloyl, carboxyaldehyde, optionally substituted alkanoyl, and optionally substituted alkyl;

each Ar L is, independently, a bivalent linker comprising optionally substituted arylene;

each R 1 is, independently, H, R S , R P , or R F ;

each Ar M is, independently, a bivalent linker comprising optionally substituted arylene;

each q is, independently, an integer of from 1 to 5;

m is an integer of from about 1 to 500;

L′ is a sublink;

wherein at least one R 1 or Ar L in formula (IV) comprises R S , R P , or R F ; and

each R L is, independently, a electrophilic reactive end group.

17. The composition of claim 16 , wherein L′ comprises a covalent bond, carbonyl, oxy, phosphonoyl, phosphoryl, sulfonyl, sulfinyl, sultam, imino, nitrilo, optionally substituted C 1-12 alkylene, optionally substituted C 1-12 alkyleneoxy, optionally substituted C 1-12 heteroalkylene, optionally substituted C 1-12 heteroalkyleneoxy, optionally substituted C 4-18 arylene, optionally substituted C 4-18 aryleneoxy, optionally substituted polyphenylene, or a structure of formula (I).

18. The composition of claim 16 , wherein R L is optionally substituted C 7-11 aryloyl or optionally substituted C 6-18 aryl.

19. A method of forming a polymer, the method comprising reacting the composition of claim 16 with a reagent having the structure of formula (V):

or a salt thereof, wherein:

each R M is, independently, a nucleophilic reactive end group;

L″ is a sublink;

Ar H is a hydrophobic segment; and

n is an integer of from about 1 to 500,

thereby promoting a nucleophilic addition reaction of R M as a nucleophile and R L as an electrophile in order to provide the polymer.

20. The method of claim 19 , further comprising sulfonating the polymer by attaching one or more R S , wherein R S is an acid moiety comprising a sulfonyl group.

21. The method of claim 19 , further comprising phosphonating the polymer by attaching one or more R P , wherein R P is an acidic moiety comprising a phosphoryl group.

22. The method of claim 19 , further comprising protecting the polymer by attaching one or more R F , wherein R F is an electron-withdrawing moiety.