Proton exchange membranes for electrochemical reactions

A proton-conducting polymer comprising a plurality of repeating units of formula (I)

• wherein one or more of Ar1, Ar2, and X1 comprises an acid functional group, wherein the acid functional group comprises —SO3−Z+, —COO−Z+, or —PO3H−Z+, and wherein Z+ is H+, a metal cation, a quaternary ammonium cation, or mixtures thereof;
• wherein Ar1 is selected from the group consisting of:
• and mixtures thereof;
• wherein Ar2 is selected from the group consisting of:
• and mixtures thereof;
• and
• wherein X1 is selected from the group consisting of:
• or a mixture of
• one or more of:
• wherein R1-R36 are each independently hydrogen, a halogen, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group, and wherein the alkyl group, the alkenyl group, the alkynyl group, or the aryl group is optionally substituted with a halogen, an acid functional group, or the halogen and the acid functional group, and wherein the acid functional group is —SO3−Z1+, —COO−Z1+, or —PO3H−Z1+, and wherein Z1+ is H+, a metal cation, a quaternary ammonium cation, or mixtures thereof;
• wherein R37-R39 are each independently hydrogen, a halogen, a nitro group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or an alkoxy group, and wherein the alkyl group, the alkenyl group, the alkynyl group, or the aryl group is optionally substituted with a halogen, an acid functional group, or the halogen and the acid functional group, and wherein the acid functional group is —SO3−Z2+, —COO−Z2+, or —PO3H−Z2+, and wherein Z2+ is H+, a metal cation, a quaternary ammonium cation, or mixtures thereof;
• wherein R40 is an alkyl group, an alkenyl group, an alkynyl group, or an aryl group, and wherein the alkyl group, the alkenyl group, the alkynyl group, or the aryl group is optionally substituted with a halogen, an acid functional group, or the halogen and the acid functional group, and wherein the acid functional group is —SO3−Z3+, —COO−Z3+, or —PO3H−Z3+, and wherein Z3+ is H+, a metal cation, a quaternary ammonium cation, or mixtures thereof;
• wherein R50, R50′, R50″, and R50′″ are each independently hydrogen, a substituted alkyl group, a substituted alkenyl group, a substituted alkynyl group, or a substituted aryl group, and wherein the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, or the substituted aryl group are substituted with an acid functional group or are substituted with a halogen and the acid functional group;
• wherein the acid functional group is —SO3−Z4+, —COO−Z4+, or —PO3H−Z4+, and wherein Z4+ is H+, a metal cation, a quaternary ammonium cation, or mixtures thereof;
• with the proviso that one or more of R50 and R50′ is not hydrogen, or one or more of R50, R50′, R50″, and R50′″ is not hydrogen;
• wherein R100 is independently a substituted alkyl group, a substituted alkenyl group, a substituted alkynyl group, or a substituted aryl group, and wherein the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, or the substituted aryl group is substituted with an acid functional group or is substituted with a halogen and the acid functional group;
• wherein the acid functional group is —SO3−Z4+, —COO−Z4+, or —PO3H−Z4+, and wherein Z4+ is H+, a metal cation, a quaternary ammonium cation, or mixtures thereof;
• wherein the halogen is F, Cl, Br, or I;
• wherein A1, A2, and A3 are each independently O, S, or N—R200 and wherein R200 is hydrogen, a substituted alkyl group, a substituted alkenyl group, a substituted alkynyl group, or a substituted aryl group, and wherein the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, or the substituted aryl group is substituted with an acid functional group or is substituted with a halogen and the acid functional group;
• wherein the acid functional group is —SO3−Z4+, —COO−Z4+, or —PO3H−Z4+, and wherein Z4+ is H+, a metal cation, a quaternary ammonium cation, or mixtures thereof;
• wherein p is 1, 2, 3, or 4;
• wherein q is 0, 1, 2, or 3;
• wherein r, s, t, and o are independently 0, 1, 2, 3, 4, 5, or 6;
• and
• wherein n is an integer from 0 to 5000;
• wherein m is an integer from 5 to 5000;
• and
• wherein a molar ratio of n/m is in a range of 0:1 to 20:1.