Flame retardant polymers with exchangeable counterions for enhanced properties

Abstract

A polymer comprising pyridinium salt moieties, wherein the polymer has the following structure: In this structure, R1 and R6 are each N. At least a portion of R2 and R7 groups in the polymer are each negatively charged counterions selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatob orates, metaborates, phosphorus-containing anions, halides, sulfates, SO4 -2, HSO4 -1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof. R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups including one or more carbon atoms. R5 and R10 are any group including one or more carbon atoms. The n is an integer from 2 to about 100,000.

Description

[0001] Thorpe North & Western, LLP Docket No.: 4917-002.PCT FLAME RETARDANT POLYMERS WITH EXCHANGEABLE COUNTERIONS FOR ENHANCED PROPERTIES PRIORITY DATA This application claims the benefit of U.S. Provisional Patent Application No. 63 / 631,292, filed April 8, 2024, which is hereby incorporated herein by reference in its entirety. TECHNOLOGY FIELD The present technology involves flame resistant / retardant polymers and uses therefore. Accordingly, this technology involves the fields of chemistry and materials sciences. BACKGROUND Polymers and polymeric materials are used in a very wide array of products across many industries. Depending on the nature and intended use of a given product, polymers which contribute flame resistant / retardant properties to the product can be very useful. In fact, government requirements regarding a degree of fire resistance / retardance have been imposed on many products across many industries. Examples of such industries include construction, automobiles, boats, aircraft, adhesives, insulation for electronics, textiles, and others. In practice, some polymers are made more flame resistant / retardant by adding a flame resistant / retardant additive, such as polychlorinated biphenyls or brominated flame retardants. Unfortunately, implementation of some flame resistant / retardant additives comes with a number of negative tradeoffs and poses environmental and health risks. SUMMARY The present disclosure describes flame resistant / retardant polymers with exchangeable counterions. A variety of polymers and methods of making the polymers are described. The polymers can include pyridinium salt moieties, where the pyridinium salt can include a counterion that may be exchanged for a variety of different counterions to alter the properties of the polymers. In one example, a polymer comprising pyridinium salt moieties can have the following structure: Thorpe North & Western, LLP Docket No.: 4917-002.PCT R7 are each negatively charged counterions; R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; R5 is any group comprising one or more carbon atoms; and R10 has the following structure: about 70. The n is an integer from 2 to about 100,000. In certain examples, R5 can be devoid of phosphorus atoms. R5 can include a phenylene group in some examples. In certain examples, at least one of R3, R4, R8, or R9 can include a phenyl group. In further examples, x can be an integer from 2 to 5, or from 5 to 10, or from 30 to 35, or from 65 to 70. In some cases, R2 and R7 can be tosylate counterions or triflimide counterions. A first portion of the R2 and R7 groups can be tosylate counterions or triflimide counterions, and a second portion of the R2 and R7 groups can be exchanged for a different counterion in some examples. The first portion can include from about 1% to about 33% of the R2 and R7 groups and the second portion can include from about 67% to about 99% of the R2 and R7 groups. In some examples, the different counterion can include a negatively charged counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof. In other examples, at least a portion of the R2 and R7 groups can include a negatively charged counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, Thorpe North & Western, LLP Docket No.: 4917-002.PCT metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus- containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof. In further examples, at least a portion of the R2 and R7 groups can include a negatively charged counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof. In still further examples, at least a portion of the R2 and R7 groups can include dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2- ethylehexyl) hydrogen phosphate, or a combination thereof. In alternative examples, at least a portion of the R2 and R7 groups can include sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof. In other examples, at least a portion of the R2 and R7 groups can include benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarcosinate, stearate, or a combination thereof. In further examples, at least a portion of the R2 and R7 groups can include tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, tetrafluoroborate, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p- tolyl)borate, or a combination thereof. Another polymer comprising pyridinium salt moieties can have the following structure: Thorpe North & Western, LLP Docket No.: 4917-002.PCT R7 groups in the polymer are each negatively charged counterions selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof; R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; R5 and R10 are any group comprising one or more carbon atoms; and n is an integer from 2 to about 100,000. In some examples, R5 can be devoid of phosphorus atoms. In further examples, R10 can be devoid of phosphorus atoms. A first portion of the R2 and R7 groups can be tosylate counterions or triflimide counterions, and a second portion of the R2 and R7 groups can be the negative charged counterions. The first portion can include from about 1% to about 33% of the R2 and R7 groups and the second portion can include from about 67% to about 99% of the R2 and R7 groups. In some examples, at least a portion of the R2 and R7 groups can include dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof. In certain examples, at least a portion of the R2 and R7 groups can include lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof. In other examples, at least a portion of the R2 and R7 groups can include comprise benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof. In Thorpe North & Western, LLP Docket No.: 4917-002.PCT still further examples, at least a portion of the R2 and R7 groups can include tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof. In some examples, R10 can include at least one of the following structures: , Thorpe North & Western, LLP Docket No.: 4917-002.PCT , 70. Another example polymer comprising pyridinium salt moieties can have the following structure: R7 groups in the polymer are each negatively charged counterions selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof; R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; R5 and R10 are any group comprising one or more carbon atoms and which are devoid of phosphorus atoms; and n is an integer from 2 to about 100,000. In some examples, a first portion of the R2 and R7 groups are tosylate counterions or triflimide counterions, and a second portion of the R2 and R7 groups are the negative charged counterions. The first portion can include from about 1% to about 33% of the R2 and R7 groups and the second portion can include from about 67% to about 99% of the R2 and R7 groups. At least a portion of the R2 and R7 groups can include dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof. Thorpe North & Western, LLP Docket No.: 4917-002.PCT In further examples, at least a portion of the R2 and R7 groups can include sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof. In other examples, at least a portion of the R2 and R7 groups can include benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof. In further examples, at least a portion of the R2 and R7 groups can include tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof. In still further examples, R10 can include at least one of the following structures: , Thorpe North & Western, LLP Docket No.: 4917-002.PCT , 70. An example flame-retardant polymer comprising pyridinium salt moieties can have the following structure: R7 groups in the polymer are each negatively charged flame-retardant counterions; R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; R5 and R10 are any group comprising one or more carbon atoms and which are devoid of phosphorus atoms; and n is an integer from 2 to about 100,000. In some examples, a first portion of the R2 and R7 groups are tosylate counterions or triflimide counterions, and a second portion of the R2 and R7 groups are the negative charged counterions. In certain examples, the first portion can include from about 1% to about 33% of the R2 and R7 groups and the second portion can include from about 67% to about 99% of the R2 and R7 groups. In some examples, at least a portion of the R2 and R7 groups can include dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof. In other examples, at least a portion of the R2 and R7 groups can include sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, Thorpe North & Western, LLP Docket No.: 4917-002.PCT persulfate, methanesulfonate, or a combination thereof. In further examples, at least a portion of the R2 and R7 groups can include benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof. In still further examples, at least a portion of the R2 and R7 groups can include tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof. In some examples, R10 can include at least one of the following structures: , wherein x is an integer from 2 to about 70. Thorpe North & Western, LLP Docket No.: 4917-002.PCT Another example can include a polymer mixture having a base polymer mixed with a flame-retardant polymeric additive. The flame-retardant polymeric additive can have the following structure: R7 groups in the polymer are each negatively charged counterions selected to modulate compatibility of the flame-retardant polymeric additive with the base polymer; R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; R5 and R10 are any group comprising one or more carbon atoms; and n is an integer from 2 to about 100,000. In some examples, the base polymer can include polyolefins, polyacrylonitriles, polystyrenes, polyamides, polyimides, polyethers, polyester, polycarbonates, polyurethanes, viscose rayon, cellulous acetate, epoxies, natural and synthetic rubbers, or a combination thereof. The mixture can include from 50% to 99% of the base polymer and from about 1% to about 50% of the flame retardant polymeric additive. In certain examples, a first portion of the R2 and R7 groups can be tosylate counterions or triflimide counterions, and a second portion of the R2 and R7 groups can be the negative charged counterions. The first portion can include from about 1% to about 33% of the R2 and R7 groups and the second portion can include from about 67% to about 99% of the R2 and R7 groups. In some examples, at least a portion of the R2 and R7 groups can include dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof. In further examples, at least a portion of the R2 and R7 groups can include sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl Thorpe North & Western, LLP Docket No.: 4917-002.PCT ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof. In other examples, at least a portion of the R2 and R7 groups can include benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof. In still further examples, at least a portion of the R2 and R7 groups can include tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof. In some examples, R10 can include at least one of the following structures: , Thorpe North & Western, LLP Docket No.: 4917-002.PCT The present disclosure also describes methods of making the polymers. In one example, a method of making a counterion-exchanged polymer includes: reacting a bispyrylium monomer comprising a first counterion with a diamine monomer using a ring-transmutation polymerization reaction to form a first polymer, wherein the diamine monomer is devoid of phosphorus atoms; exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof; and recovering the first polymer with the second counterion as a counterion-exchanged polymer. In some examples, the exchanging is performed by dissolving the first polymer in a solvent and dissolving a salt comprising the second counterion in the solvent, then adding a non-solvent to precipitate the counterion-exchanged polymer. In other examples, the exchanging is performed by dissolving a salt comprising the second counterion in water, dissolving the first polymer in a solvent, then adding the solvent with the dissolved first polymer to the water with the dissolved salt, thereby precipitating the counterion-exchanged polymer, wherein the solvent is a water-miscible solvent. In further examples, the exchanging is performed by dissolving the first polymer in a solvent and passing the solvent with the dissolved first polymer through an ion-exchange column containing the second counterion. In still further examples, the exchanging is performed by dissolving the first polymer in a solvent and placing the solvent with the dissolved first polymer in contact with a dialysis membrane, and placing a Thorpe North & Western, LLP Docket No.: 4917-002.PCT solution comprising the second counterion in contact with an opposite side of the dialysis membrane. In other examples, the exchanging can be performed by milling the first polymer with a salt comprising the second counterion for a time sufficient to exchange at least a portion of the first counterion with the second counterion. In further examples, the exchanging can be performed by melting the first polymer and a salt comprising the second counterion and mixing the melted polymer and salt together. In some examples, the first counterion can include tosylate counterions or triflimide counterions. In further examples, the counterions in the counterion-exchanged polymer can include from about 1% to about 33% of the first counterion and from about 67% to about 99% of the second counterion. In some examples, the second counterion can include dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof. In other examples, the second counterion can include sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof. In still other examples, the second counterion can include benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof. In further examples, the second counterion can include tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof. In some examples, the diamine monomer can include at least one of the following structures: Thorpe North & Western, LLP Docket No.: 4917-002.PCT , , wherein x is an integer from 2 to about 70. Another example method of making a counterion-exchanged polymer can include: dissolving a bispyrylium monomer comprising a first counterion in a solvent; exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof to form a counterion- exchanged bispyrylium monomer; and reacting the counterion-exchanged bispyrylium monomer with a diamine monomer using a ring-transmutation polymerization reaction to form a counterion-exchanged polymer, wherein the diamine monomer is devoid of phosphorus atoms. In some examples, the exchanging is performed by dissolving a salt comprising the second counterion in the solvent, then adding a non-solvent to precipitate the counterion- Thorpe North & Western, LLP Docket No.: 4917-002.PCT exchanged bispyrylium monomer. In further examples, the exchanging is performed by dissolving a salt comprising the second counterion in water, then adding the solvent with the dissolved bispyrylium monomer to the water with the dissolved salt, thereby precipitating the counterion-exchanged bispyrylium monomer, wherein the solvent is a water-miscible solvent. In still further examples, the exchanging is performed by passing the solvent with the dissolved bispyrylium monomer through an ion-exchange column containing the second counterion. In other examples, the exchanging is performed by placing the solvent with the dissolved bispyrylium monomer in contact with a dialysis membrane, and placing a solution comprising the second counterion in contact with an opposite side of the dialysis membrane. In some examples, the first counterion can include tosylate counterions or triflimide counterions. In further examples, the counterions in the counterion-exchanged polymer can include from about 1% to about 33% of the first counterion and from about 67% to about 99% of the second counterion. In some examples, the second counterion can include dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof. In other examples, the second counterion can include sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof. In further examples, the second counterion can include benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof. In still further examples, the second counterion can include tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof. In some examples, the diamine monomer can include at least one of the following structures: Thorpe North & Western, LLP Docket No.: 4917-002.PCT , , wherein x is an integer from 2 to about 70. Another example method of making a counterion-exchanged polymer can include: reacting a bispyrylium monomer comprising a first counterion with a diamine monomer using a ring-transmutation polymerization reaction to form a first polymer; exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof; and recovering the first polymer with the second counterion as a counterion-exchanged polymer. In some examples, the exchanging is performed by dissolving the first polymer in a solvent and dissolving a salt comprising the second counterion in the solvent, then adding a non-solvent to precipitate the counterion- Thorpe North & Western, LLP Docket No.: 4917-002.PCT exchanged polymer. In other examples, the exchanging is performed by dissolving a salt comprising the second counterion in water, dissolving the first polymer in a solvent, then adding the solvent with the dissolved first polymer to the water with the dissolved salt, thereby precipitating the counterion-exchanged polymer, wherein the solvent is a water-miscible solvent. In further examples, the exchanging is performed by dissolving the first polymer in a solvent and passing the solvent with the dissolved first polymer through an ion-exchange column containing the second counterion. In still further examples, the exchanging is performed by dissolving the first polymer in a solvent and placing the solvent with the dissolved first polymer in contact with a dialysis membrane, and placing a solution comprising the second counterion in contact with an opposite side of the dialysis membrane. In other examples, the exchanging can be performed by milling the first polymer with a salt comprising the second counterion for a time sufficient to exchange at least a portion of the first counterion with the second counterion. In further examples, the exchanging can be performed by melting the first polymer and a salt comprising the second counterion and mixing the melted polymer and salt together. In some examples, the first counterion can include tosylate counterions or triflimide counterions. In certain examples, the counterions in the counterion-exchanged polymer can include from about 1% to about 33% of the first counterion and from about 67% to about 99% of the second counterion. In some examples, the second counterion can include dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof. In other examples, the second counterion can include lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof. In further examples, the second counterion can include benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof. In still further examples, the second counterion can include tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, Thorpe North & Western, LLP Docket No.: 4917-002.PCT pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof. In some examples, the diamine monomer can include at least one of the following structures:

[0002] Thorpe North & Western, LLP Docket No.: 4917-002.PCT , , wherein x is an integer from 2 to about 70. Another example method of making a counterion-exchanged polymer can include: dissolving a bispyrylium monomer comprising a first counterion in a solvent; exchanging the Thorpe North & Western, LLP Docket No.: 4917-002.PCT first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof to form a counterion-exchanged bispyrylium monomer; and reacting the counterion-exchanged bispyrylium monomer with a diamine monomer using a ring-transmutation polymerization reaction to form a counterion- exchanged polymer. In some examples, the exchanging is performed by dissolving a salt comprising the second counterion in the solvent, then adding a non-solvent to precipitate the counterion-exchanged bispyrylium monomer. In other examples, the exchanging is performed by dissolving a salt comprising the second counterion in water, then adding the solvent with the dissolved bispyrylium monomer to the water with the dissolved salt, thereby precipitating the counterion-exchanged bispyrylium monomer, wherein the solvent is a water-miscible solvent. In further examples, the exchanging is performed by passing the solvent with the dissolved bispyrylium monomer through an ion-exchange column containing the second counterion. In still further examples, the exchanging is performed by placing the solvent with the dissolved bispyrylium monomer in contact with a dialysis membrane, and placing a solution comprising the second counterion in contact with an opposite side of the dialysis membrane. In some examples, the first counterion can include tosylate counterions or triflimide counterions. In certain examples, the counterions in the counterion-exchanged polymer can include from about 1% to about 33% of the first counterion and from about 67% to about 99% of the second counterion. In some examples, the second counterion can include dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof. In other examples, the second counterion can include lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof. In further examples, the second counterion can include benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a Thorpe North & Western, LLP Docket No.: 4917-002.PCT combination thereof. In still further examples, the second counterion can include tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl) borate, or a combination thereof. In some examples, the diamine monomer can include at least one of the following structures: , , wherein x is an integer from 2 to about 70. Thorpe North & Western, LLP Docket No.: 4917-002.PCT BRIEF DESCRIPTION OF THE DRAWINGS Additional features and advantages of invention embodiments will be apparent from the detailed description which follows, taken in conjunction with the accompanying drawings, which together illustrate, by way of example, features of the invention; and, wherein: FIG. 1 is a chemical structure of an example polymer in accordance with the present technology. FIG. 2 is a chemical structure of another example polymer in accordance with the present technology. FIG. 3 is a chemical structure of an example monomer that can be used to make a polymer in accordance with the present technology. FIG. 4 shows chemical structures of several example counterions that can be used to make a polymer in accordance with the present technology. FIG.5 shows chemical structures of several example sulfur based counterions that can be used to make a polymer in accordance with the present technology. FIG.6 shows chemical structures of several example carbon based counterions that can be used to make a polymer in accordance with the present technology. FIG.7 shows chemical structures of several example boron based counterions that can be used to make a polymer in accordance with the present technology. FIG.8 shows a chemical structure of another example polymer in accordance with the present technology. FIG. 9 shows a graph of differential scanning calorimetry (DSC) data for an example polymer in accordance with the present technology. FIG. 10 shows a graph of thermogravimetric analysis (TGA) data for an example polymer in accordance with the present technology. FIG. 11 shows a graph of differential scanning calorimetry (DSC) data for another example polymer in accordance with the present technology. FIG. 12 shows a graph of differential scanning calorimetry (DSC) data for another example polymer in accordance with the present technology. FIG. 13 shows a graph of differential scanning calorimetry (DSC) data for another example polymer in accordance with the present technology. Thorpe North & Western, LLP Docket No.: 4917-002.PCT Reference will now be made to the exemplary embodiments illustrated, and specific language will be used herein to describe the same. It will nevertheless be understood that no limitation of the scope of the invention is thereby intended. DETAILED DESCRIPTION OF EXAMPLE EMBODIMENTS Before invention embodiments are described, it is to be understood that this disclosure is not limited to the particular structures, process steps, or materials disclosed herein, but is extended to equivalents thereof as would be recognized by those ordinarily skilled in the relevant arts. It should also be understood that terminology employed herein is used for the purpose of describing particular examples or embodiments only and is not intended to be limiting. The same reference numerals in different drawings represent the same element. Numbers provided in flow charts and processes are provided for clarity in illustrating steps and operations and do not necessarily indicate a particular order or sequence. Furthermore, the described features, structures, or characteristics can be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided, such as examples of compositions, dosage forms, treatments, etc., to provide a thorough understanding of various invention embodiments. One skilled in the relevant art will recognize, however, that such detailed embodiments do not limit the overall inventive concepts articulated herein, but are merely representative thereof. It should be noted that as used herein, the singular forms “a,” “an,” and, “the” include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to “a counterion” includes reference to one or more of such groups, and reference to “the polymer” includes reference to one or more of such materials. In this disclosure, “comprises,” “comprising,” “containing” and “having” and the like can have the meaning ascribed to them in U.S. Patent law and can mean “includes,” “including,” and the like, and are generally interpreted to be open ended terms. The terms “consisting of” or “consists of” are closed terms, and include only the components, structures, steps, or the like specifically listed in conjunction with such terms, as well as that which is in accordance with U.S. Patent law. “Consisting essentially of” or “consists essentially of” have the meaning generally ascribed to them by U.S. Patent law. In particular, such terms are generally closed terms, with the exception of allowing inclusion of additional items, materials, components, Thorpe North & Western, LLP Docket No.: 4917-002.PCT steps, or elements, that do not materially affect the basic and novel characteristics or function of the item(s) used in connection therewith. For example, trace elements present in a composition, but not affecting the compositions nature or characteristics would be permissible if present under the “consisting essentially of” language, even though not expressly recited in a list of items following such terminology. When using an open ended term, like “comprising” or “including,” in the written description it is understood that direct support should be afforded also to “consisting essentially of” language as well as “consisting of” language as if stated explicitly and vice versa. The terms “first,” “second,” “third,” “fourth,” and the like in the description and in the claims, if any, are used for distinguishing between similar elements and not necessarily for describing a particular sequential or chronological order. It is to be understood that any terms so used are interchangeable under appropriate circumstances such that the embodiments described herein are, for example, capable of operation in sequences other than those illustrated or otherwise described herein. Similarly, if a method is described herein as comprising a series of steps, the order of such steps as presented herein is not necessarily the only order in which such steps may be performed, and certain of the stated steps may possibly be omitted and / or certain other steps not described herein may possibly be added to the method. As used herein, comparative terms such as “increased,” “decreased,” “better,” “worse,” “higher,” “lower,” “enhanced,” “maximized,” “minimized,” and the like refer to a property of a device, component, composition, or activity that is measurably different from other devices, components, compositions or activities that are in a surrounding or adjacent area, that are similarly situated, that are in a single device or composition or in multiple comparable devices or compositions, that are in a group or class, that are in multiple groups or classes, or as compared to the known state of the art. Occurrences of the phrase “in one embodiment,” or “in one aspect,” herein do not necessarily all refer to the same embodiment or aspect. As used herein, the term “substantially” refers to the complete or nearly complete extent or degree of an action, characteristic, property, state, structure, item, or result. For example, an object that is “substantially” enclosed would mean that the object is either completely enclosed or nearly completely enclosed. The exact allowable degree of deviation from absolute completeness may in some cases depend on the specific context. However, generally speaking Thorpe North & Western, LLP Docket No.: 4917-002.PCT the nearness of completion will be so as to have the same overall result as if absolute and total completion were obtained. The use of “substantially” is equally applicable when used in a negative connotation to refer to the complete or near complete lack of an action, characteristic, property, state, structure, item, or result. For example, a composition that is “substantially free of” a certain compound would either completely lack that compound, or so nearly completely lack the compound that the effect would be the same as if it completely lacked the compound. In other words, a composition that is “substantially free of” an ingredient or element may still actually contain such item as long as there is no measurable effect thereof. As used herein, the term “about” is used to provide flexibility to a numerical range endpoint by providing that a given value may be “a little above” or “a little below” the endpoint. Unless otherwise stated, use of the term “about” in accordance with a specific number or numerical range should also be understood to provide support for such numerical terms or range without the term “about”. For example, for the sake of convenience and brevity, a numerical range of “about 50 angstroms to about 80 angstroms” should also be understood to provide support for the range of “50 angstroms to 80 angstroms.” Furthermore, it is to be understood that in this specification support for actual numerical values is provided even when the term “about” is used therewith. For example, the recitation of “about” 30 should be construed as not only providing support for values a little above and a little below 30, but also for the actual numerical value of 30 as well. As used herein, “flame retardant” and “fire retardant” refers to a property of a substance that allows the substance to slow down ignition and burning, either of the fire retardant substance itself or of surrounding materials. As used herein, “flame resistant” and “fire resistant” refers to a property of a substance that allows the substance to withstand high heat for extended periods of time without catching fire. It is noted that the polymers described herein can often have both fire retardant and fire resistant properties, and therefore the polymers are referred to herein interchangeably as fire retardant polymers and fire resistant (or flame retardant or flame resistant) polymers. As used herein, the term “at least one of” is intended to be synonymous with “one or more of.” For example, “at least one of A, B and C” and “at least one of A, B, or C” explicitly include only A, only B, only C, or combinations of each. Thorpe North & Western, LLP Docket No.: 4917-002.PCT As used herein, a plurality of items, structural elements, compositional elements, and / or materials may be presented in a common list for convenience. However, these lists should be construed as though each member of the list is individually identified as a separate and unique member. Thus, no individual member of such list should be construed as a de facto equivalent of any other member of the same list solely based on their presentation in a common group without indications to the contrary. Concentrations, amounts, levels and other numerical data may be expressed or presented herein in a range format. It is to be understood that such a range format is used merely for convenience and brevity and thus should be interpreted flexibly to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges or decimal units encompassed within that range as if each numerical value and sub-range is explicitly recited. As an illustration, a numerical range of “about 1 to about 5” should be interpreted to include not only the explicitly recited values of about 1 to about 5, but also include individual values and sub-ranges within the indicated range. Thus, included in this numerical range are individual values such as 2, 3, and 4 and sub-ranges such as from 1-3, from 2-4, and from 3-5, etc., as well as 1, 2, 3, 4, and 5, individually. This same principle applies to ranges reciting only one numerical value as a minimum or a maximum. Furthermore, such an interpretation should apply regardless of the breadth of the range or the characteristics being described. Reference throughout this specification to “an example” means that a particular feature, structure, or characteristic described in connection with the example is included in at least one embodiment. Thus, appearances of the phrases “in an example” in various places throughout this specification are not necessarily all referring to the same embodiment. The polymers described herein can be poly(pyridinium salt)s made using bispyrylium monomers and diamine monomers. The bispyrylium monomer can be any monomer that includes two pyrylium groups. Pyrylium is a cation with the formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom bonded thereto, and one positively charge oxygen atom. The pyrylium groups can react with amine groups in a polymerization reaction. In certain examples, the polymers can be made from 4,4’-(1,4- Phenylene)-bis(2,6-diphenylpyrylium) polymerized with a diamine monomer, and various counterions can be added to tune the polymer properties such as decomposition temperature, Thorpe North & Western, LLP Docket No.: 4917-002.PCT solubility, wettability, blending with others solids or polymers. In particular, the bispyrylium monomer can be prepared with certain initial counterions, such as tosylate or triflimide counterions. These can be negative anions that balance the positive charge of the pyrylium groups. In some examples, a portion or all of the initial counterions can be exchanged for a variety of different counterions. Various counterions can impart different properties to the polymer. Therefore, the counterion exchange can be useful for tuning the properties of the polymer. In some examples, the polymer can have the following general chemical structure: 10 In this structure, the R10 group can be derived from the diamine monomer. The remainder of the structure can be derived from the bispyrylium monomer, with R2 and R7 being counterions that can include the original counterions that were present with the bispyrylium monomer, or other counterions that have been exchanged for the initial counterions, or some combination thereof. Additionally, R1 and R6 can each be a nitrogen atom (N) in the polymer. R5 can be any group comprising one or more carbon atoms. In certain examples, R5 can be a phenylene group. The remaining groups R3, R4, R8, R9, R13, R14, R15, and R16 can each be a hydrogen atom or a group comprising one or more carbon atoms. In certain examples, at least one of R3, R4, R8, or R9 can be a phenyl group. In a particular example, all of R3, R4, R8, and R9 can be phenyl groups, and R13, R14, R15, and R16 can be hydrogen atoms. The polymer can be made with various molecular weights, with n being an integer from 2 to about 100,000 in some examples. Some example R10 groups can have the following chemical structures: Thorpe North & Western, LLP Docket No.: 4917-002.PCT , wherein x is an integer from 2 to about 70. These R10 groups can be derived from the diamine monomer used in making the polymer. Therefore, some example diamine monomers that can be used to make the polymer can have the structures shown above, with amino (NH2) groups on either end of the structures where bonding locations are indicated by wavy lines. Other diamine monomers can also be used. In certain examples, the diamine monomer can include a Thorpe North & Western, LLP Docket No.: 4917-002.PCT phosphorous atom, while in other examples the diamine monomer can be devoid of phosphorous groups. FIG.1 shows one example polymer according to the present technology. This polymer includes a counterion that is inositol hexaphosphate having a -2 charge. Thus, each inositol hexaphosphate counterion balances the positive charge of two pyridinium groups in the polymer. FIG. 2 shows another example polymer according to the present technology. In this example, the polymer includes bis(2-ethylhexyl) phosphate as the counterion. Each counterion molecule has a -1 charge, so two of the counterion molecules are needed to balance the +2 charge of the two pyridinium groups in the polymer unit. The bispyrylium monomer can be made as the ditosylate salt as per the literature: Alam, Maksudul M., et al. "Phosphine oxide containing poly (pyridinium salt)s as fire retardant materials." Polymers 11.7 (2019): 1141, which is incorporated herein by reference. This literature also describes polymerization reactions that can be used to prepare a polymer from the bispyrylium ditosylate monomer and a diamine monomer. As an example, FIG.3 shows an example bispyrylium monomer with tosylate counterions, which can be used in the polymerization reaction. In other examples, the bispyrylium monomer can be prepared as a ditriflimide salt. The tosylate or triflimide counterions of the bispyrylium monomer can be exchanged with any number of counterions to tune various properties including solubility, decomposition temperature, blend-ability into other polymers, vary elemental composition including phosphorous, boron, nitrogen, zinc, aluminum, etc. This can be done by counterion metathesis in a single displacement reaction, double displacement reaction, ion exchange column, dialysis membrane, or other exchange processes. The initial counterions can be exchanged for other counterions either before the polymerization or after the polymerization. In some examples, a bispyrylium ditosylate monomer can be prepared and then polymerized with a diamine monomer through a ring- transmutation polymerization reaction. For example, the bispyrylium ditosylate monomer and the diamine monomer can be mixed with a solvent and heated to initiate the polymerization reaction. In this polymerization reaction, the nitrogen atoms of the diamine monomer can replace the oxygen atoms in the pyrylium groups of the bispyrylium monomer, and the oxygen can combine with hydrogen atoms from amino groups of the diamine monomer to form water. Thorpe North & Western, LLP Docket No.: 4917-002.PCT Water generated by the polymerization reaction can be removed from the mixture by distillation in some examples. Some example diamine monomers that can be used in the polymerization reaction include the following structures: , Thorpe North & Western, LLP Docket No.: 4917-002.PCT where x can be examples, x can be about 2.5 (i.e., a mixture of multiple molecules with an average x value of 2.5), or about 6.1, or about 33, or about 68. In further examples, the last structure can have various molecular weights (weight averaged) from about 200 to about 4,000. In certain examples, the molecular weight can be 230, 430, 2,000, or 4,000. The polymerization reaction can yield a polymer having the original tosylate counterions from the bispyrylium ditosylate monomer. The tosylate counterions can then be exchanged for other counterions. In alternative examples, the tosylate counterions of the bispyrylium ditosylate monomer can be exchanged with other counterions before the polymerization reaction. The bispyrylium monomer with the new counterions can then be used in a polymerization reaction in the same way as described above to form a polymer having the new counterions. The counterions exchanged for the tosylate counterions (or any other initial counterions that may be present with the bispyrylium monomer) can include a wide variety of counterions. Phosphorous based ions can increase flame retardancy and vary phosphorous content. Phosphorous based ions can increase char yield. Phosphorous ions with short or long alkyl chains can decrease brittleness and increase blending with commercial solids and polymers. Phosphorous ions with aromatic rings can decrease brittleness and increase blending with commercial solids and polymers. Boron based ions can increase flame retardancy and vary boron content. Boron based ions can increase char yield. Boron based ions with short or long alkyl chains can decrease brittleness and increase blending with commercial solids and polymers. Boron based ions with aromatic rings can decrease brittleness and increase blending with commercial solids and polymers. Sulfur based ions can increase flame retardancy and vary sulfur content. Sulfur based ions can also increase char yield. Sulfur based ions with short or long alkyl chains can decrease brittleness and increase blending with commercial solids and polymers. Sulfur based ions with aromatic rings can decrease brittleness and increase blending with commercial solids and polymers. Oxygen based ions can increase flame retardancy and Thorpe North & Western, LLP Docket No.: 4917-002.PCT vary oxygen content. Oxygen based ions can also increase char yield. Oxygen based ions with short or long alkyl chains can decrease brittleness and increase blending with commercial solids and polymers. Oxygen based ions with aromatic rings can decrease brittleness and increase blending with commercial solids and polymers. Nearly any monoanion can be used, such as halides, nitrates, dibasic phosphates, or combinations thereof. Any dianion can also be used, such as carbonate, sulfates, dibasic phosphates, boronates, and combinations thereof. Any polyanion can be used, such as phosphate, polyphosphates, mono, di, tri-, or more basic phytic acid, polysulfonates, and combinations thereof. Any anionic surfactant can be used, such as ammonium lauryl sulfate, sodium laureth sulfate, sodium lauryl sarcosinate, sodium myreth sulfate, sodium pareth sulfate, sodium stearate, sodium lauryl sulfate, α olefin sulfonate, ammonium laureth sulfate, and combinations thereof. Several example counterions are shown in FIG. 4. These counterions can be exchanged with the initial counterions, either by exchanging the counterions of the bispyrylium monomer before the polymerization, or by exchanging the counterions of the polymer after polymerization. In FIG. 4, some of the examples are shown in the ionic form, with negative charges. Others are shown as a salt with a cation, such as sodium. Still others are shown as an acid form, which can be converted to an anionic form when dissolved in water or another solvent. In some embodiments, the counter ion can be selected based on cost and / or results to be achieved, such as char effect. In this way specific polymers with specific properties (e.g. S, P, N, Si, and B content) which affect char yield and other properties vs. required cost can be prepared. Some examples of sulfur based counterions and their effects of increasing or lowering the content of certain elements include sulfate (SO4)-2, bisulfate (HSO4)-1, thiosulfate (S2O3)-2, dithionite (S2O4)-2, metabisulfate (S2O5)-2, persulfate (S2O8)-2, and methanesulfonate (CH3SO3)-1, which are inexpensive and which can be used to increase the relative amount of sulfur and reduce the relative amount of carbon in the polymer. Additionally, dodecylsulfate (CH3(CH2)11OSO3)-1is inexpensive, can be used to increase sulfur content, decrease carbon content, and can also lower the melting point of the polymer. Several example sulfur based counterions are shown in FIG.5. The examples shown include sulfonic acid, sodium dodecyl sulfate, ammonium dodecyl sulfate, ammonium lauryl sulfate, dioctyl sodium sulfosuccinate, sodium lauryl ether sulfate, sodium dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, perfluorooctanesulfonic acid, and perfluorobutanesulfonic acid. Thorpe North & Western, LLP Docket No.: 4917-002.PCT Examples of phosphorous based counterions and their effects can include phosphate mono (H2PO4)-1, phosphate di (HPO4)-2, phosphate tri (PO4)-3, tripolyphosphate (P3O10)-5, hypophosphite (HPO2)-2, pyrophosphate (P2O7)-4, pyrophosphate / dibasic (H2P2O7)-2, and hexametaphosphate (NaPO3)n, which are inexpensive and can be used to increase the relative amount of phosphorous and decrease the relative amount of carbon in the polymer. Examples of carbon based counterions and their effects include benzoate (C6H5CO2)-1, acetate (CH3CO2)-1, formate (HCO2)-1, octanoate (CH3(CH2)6CO2)-1, citrate HOC(CO2)(CH2CO2)2-3, tartrate (C6H4O6)-2, and gluconate (C6H11O7)-1, which are inexpensive and which can increase the relative amount of carbon in the polymer. Several example carbon- based counterions that can be used are shown in FIG.6. In the first structure shown in FIG.6, the values of X and Y can be any integer from 1 to about 100 in some examples. Some of the examples are shown in acid form, including capric acid, monocaprin, lauric acid, glycerol monolaurate, oleic acid, elaidic acid, linoleic acid, and α-linoleic acid. When these acids are deprotonated, their anions can be used as the counterion in the polymers described herein. Examples of nitrogen based counterions and their effects include azide (N3)-1, Nitrate (NO3)-1, and L-glutamate (C5H8NO4)-1, which are inexpensive and which can increase the relative amount of nitrogen in the polymer, decrease the relative amount of carbon in the polymer, and which can also lower the decomposition temperature of the polymer. Nitrite (NO2)-1can also increase the nitrogen content and decrease the carbon content. Combinations of these can also be used. Examples of silicon based counterions include metasilicate Na2O3Si ^ 9H2O, which is inexpensive, increases the relative amount of silicon in the polymer, decreases the relative amount of carbon in the polymer, and increases char yield. Examples of boron based counterions include borate (B4O7)-2and perborate (BO3)-1, which are inexpensive and which can increase the relative amount of boron in the polymer, decrease the relative amount of carbon in the polymer, and increase char yield. FIG. 7 also shows several example boron-based counterions that can be used in the polymer. Many of the examples are shown in salt form. Some of the examples include tris-pentafluorophenyl borane, lithium bis-oxalato borate, lithium difluoro(oxalate)borate, lithium borohydride, lithium tetrafluoroborate, boron nitride, lithium metaborate, trimethyl borate, butylboronic acid, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron Thorpe North & Western, LLP Docket No.: 4917-002.PCT oxide, bis(oxalate)borate, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, sodium borate, and sodium tetratolyl borate. In a particular embodiment the counterions of the monomer are exchanged before the monomer is polymerized to form the polymer. For example, the ditosylate monomer can be dissolved in a solvent good for both the monomer and the salt containing the counter ion. In certain examples, the ditosylate monomer can be dissolved in methanol, acetonitrile, or DMSO depending upon the solubility of the exchanging salt. Subsequently, 5-20 equivalents of the salt can be combined, and the solution can be stirred for 1-24 hours. This solution is then poured into a non-solvent to precipitate the monomer as a solid. In some examples, the non-solvent can be water. The subsequent solid is collected. Elemental analysis can be used to confirm the presence of the salt exchanged by elemental differences. In another example, the monomers can be polymerized to form a polymer and then the counterions of the polymer can be exchanged with other counterions. For example, the ditosylate polymer can be dissolved in a solvent good for both the polymer and the salt containing the counter ion. In one embodiment, the ditosylate polymer can be dissolved in methanol, acetonitrile, or DMSO depending upon the solubility of the polymer and exchanging salt. Subsequently, 5-20 equivalents of the salt can be added, and the solution is stirred for 1- 24 hours. This solution is then poured into a non-solvent to precipitate the polymer as a solid. In one example, the non-solvent can be water. The subsequent solid is collected. Elemental analysis can be used to confirm the present of salt exchanged by elemental differences. Example processes that can be used to produce the ion exchanged polymers can include solution displacement. In this process, both polymer and salt are in the same solvent and then precipitated into a non-solvent. In another example, the process can involve solution displacement of the monomer, in which both the monomer and salt are in the same solvent and then precipitated into a non-solvent. Another example process can involve precipitation displacement of the monomer. The monomer can be dissolved in a water miscible solvent and then the solution can be precipitated into water containing 1-100 equivalents of the salt with the exchanging anion. Another example process can involve precipitation displacement of the polymer. The polymer can be dissolved in a water miscible solvent and then the solution can be precipitated into water containing 1-100 equivalents of the salt with the exchanging anion. Another example process can involve ion exchange column displacement of the monomer. The Thorpe North & Western, LLP Docket No.: 4917-002.PCT monomer can be run through an ion exchange column containing the new counter ion and then isolated. In another example, ion exchange column displacement of the polymer can be performed by running the polymer in through an ion exchange column containing the new counter ion and then the polymer can be isolated. Another example can involve dialysis displacement of the monomer, in which the monomer is dissolved in an appropriate solvent and placed in a dialysis tube and then placed in a bath with the anion to be exchanged. Dialysis displacement can also be performed with the polymer, in which the polymer is dissolved in an appropriate solvent and placed in a dialysis tube and then placed in a bath with the anion to be exchanged. In one example, a method of making the polymer can include a monomer solution displacement process. In this example, the ditosylate monomer can be dissolved in a solvent good for both the monomer and the salt containing the counter ion. In certain examples, the ditosylate monomer can be dissolved in methanol, acetonitrile, DMSO or another appropriate solvent depending upon the solubility of the exchanging salt. Subsequently, 5-20 equivalents of the salt can be added, and the solution can be stirred for 1-24 hours. This solution is then poured into a non-solvent to precipitate the monomer. In one example, the non-solvent can be water. The subsequent solid is collected and analyzed. Elemental analysis can be used to confirm the present of salt exchanged by elemental differences. In another example, a method of making the polymer can include a polymer solution displacement process. The ditosylate polymer can be dissolved in a solvent good for both the polymer and the salt containing the counter ion. In certain examples, the ditosylate polymer can be dissolved in methanol, acetonitrile, DMSO or other appropriate solvent depending upon the solubility of the polymer and exchanging salt. Subsequently, 5-20 equivalents of the salt can be combined, and the solution is stirred for 1-24 hours. This solution is then poured into a non- solvent to precipitate the polymer. In one example, the non-solvent can be water. The subsequent solid is collected and analyzed. Elemental analysis can be used to confirm the present of salt exchanged by elemental differences. In another example, a method of making the polymer can include a monomer precipitation displacement process. For salts that do not dissolve in methanol, acetonitrile, DMSO or propylene carbonate, the salts can be dissolved in water and the ditosylate monomer can be dissolved in a water miscible solvent. The monomer can then be precipitated by pouring Thorpe North & Western, LLP Docket No.: 4917-002.PCT the solution into water containing 5-20 equivalents of the salt. The monomer solid can be collected, purified for polymerization, and analyzed. In another example, a method of making the polymer can include a polymer precipitation displacement process. For salts that do not dissolve in methanol, acetonitrile, DMSO or propylene carbonate, the salts can be dissolved in water and the ditosylate polymer can be dissolved in a water miscible solvent. The polymer can then be precipitated by pouring the solution into water containing 5-20 equivalents of the salt. The polymer solid can be collected, dried and analyzed. In some examples, between 33% and 66% of the counter ions can be exchanged in just one precipitation. In a particular example, mono sodium phosphate can be used as the counterion salt, and about 33% of the counterions in the polymer can be exchanged in a single precipitation. In another example, sodium chloride can be used as the counterion salt, and about 66% of the counterions in the polymer can be exchanged in a single precipitation. In another example, a method of making the polymer can include an ion exchange column monomer displacement process. To ensure complete substitution of the tosylate ions, an ion exchange resin with an anion of interest can be used. The ditosylate monomer can be dissolved into methanol or other appropriate solvent and the solution can be run through the column. The solution is collected, and the pure monomer can be isolated and analyzed. This method can be used for many ions including but not limited to citrate, HSO4-, NO3-, HSO3-, NO2-, Cl-, HCO3-, H2PO4-,HPO4-, formate, acetate, and / or propionate. In another example, a method of making the polymer can include an ion exchange column polymer displacement process. To ensure complete substitution of the tosylate ions, an ion exchange resin with an anion of interest can be used. The ditosylate polymer can be dissolved into methanol or other appropriate solvent and the solution can be run through the column. The solution is collected, and the pure polymer can be isolated and analyzed. This method can be used for many ions including but not limited to citrate, HSO4-, NO3-, HSO3-, NO2-, Cl-, HCO3-, H2PO4-,HPO4-, formate, acetate, and / or propionate. These ion exchange columns can be made by using an anion exchange resin including but not limited to AmberLite™ FPA66 Anion Exchange Resin free base and then adding a 1N solution of an acid or acidic salt through the column. To change to a higher selective ion, 2-5 bed volumes of 1N Thorpe North & Western, LLP Docket No.: 4917-002.PCT solution of the new counterion can be passed through the sorbent. To change to a lower selective ion, 5-65 bed volumes of 1N solution of the new counterion can be passed through the sorbent. In another example, a method of making the polymer can include a dialysis monomer displacement process. The ditosylate monomer can be dissolved in an appropriate solvent including but not limited to methanol. The solution can be placed in a dialysis tube or bag with a molecular weight cutoff of 300 Daltons and then placed in a bath with the anion to be exchanged. After 1-10 exchanges of the bath solution, with the preferred number of exchanges being 2-4, the solution in the dialysis tube can be collected and the solvent can be removed. The monomer can then be dried and analyzed. In another example, a method of making the polymer can include a dialysis polymer displacement process. The ditosylate polymer can be dissolved in an appropriate solvent including but not limited to methanol. The solution can be placed in a dialysis tube or bag with a molecular weight cutoff of 10,000 Daltons and then placed in a bath with the anion to be exchanged. After 1-10 exchanges of the bath solution, with the preferred number of exchanges being 2-4, the solution in the dialysis tube can be collected. The solvent can be removed. The polymer can then be dried and analyzed. The polymers described herein can include fire retardant monomers and polymers based on Poly(pyridinium salt)s made from 4,4’-(1,4-Phenylene)-bis(2,6-diphenylpyrylium) with various counter ions to tune the polymer properties such as decomposition temperature, solubility, wettability, blending with others solids or polymers. In some examples, bispyrylium ditosylate monomer can be a basic building block for the design and development of ionic polymers having fire retardant properties. The bispyrylium ditosylate monomer contains a stable phenyl group and heteroatom in the aromatic ring that increases the thermal stability. The polymers made from the bispyrylium ditosylate monomer are cationic polymers and hence, have great potential for building up multilayer assemblies with anionic polymers by sequential electrostatic deposition technique. The bispyrylium ditosylate monomer is capable of being exchanged with any number of counter ions to tune various fire retarding properties of the bispyrylium ditosylate monomer including solubility, decomposition temperature, blend-ability into other polymers, varying elemental composition including phosphorous, boron, nitrogen, zinc, aluminum and the like. In an embodiment, the exchange of the cation with counter ions is done by counterion metathesis Thorpe North & Western, LLP Docket No.: 4917-002.PCT in a single displacement reaction, double displacement reaction, ion exchange column and / or combination thereof. In particular embodiment, the present invention provides a bispyrylium ditosylate monomer. Specifically, the bispyrylium ditosylate monomer is 4,4’-(1,4-Phenylene)-bis(2,6- diphenylpyrylium) ditosylate monomer. The bispyrylium ditosylate monomer is capable of being exchanged with a number of counter ions. In an embodiment, the counter ions are selected from but not limited to phosphorous based ions, nitrogen-based ions, silicon-based ions, aliphatic and aromatic carbonate-based ions, sulfur-based ions, oxygen-based ions, boron-based ions, sulfur-based ions, oxygen-based ions, monoanions, dianions, polyanions, anionic surfactants and the like. In another embodiment, the present invention provides a bispyrylium ditosylate polymer. Specifically, the bispyrylium ditosylate polymer is 4,4’-(1,4-Phenylene)-bis(2,6- diphenylpyrylium) ditosylate polymer. The bispyrylium ditosylate polymer is capable of being exchanged with a number of counter ions. The counter ions are selected from but not limited phosphorous-based ions, boron-based ions, nitrogen-based ions, silicon-based ions, aliphatic and aromatic carbonate-based ions, sulfur-based ions, oxygen-based ions, monoanions, dianions, polyanions and anionic surfactants. In another aspect, the present invention provides a method of preparation of the fire- retardant material using a bispyrylium ditosylate monomer as a base material. At a first step, the method can comprise preparing bispyrylium ditosylate monomer i.e.4,4’-(1,4-Phenylene)- bis(2,6-diphenylpyrylium) ditosylate monomer. The bispyrylium ditosylate monomer can be prepared by first reacting terephthalaldehyde and acetophenone in ethanol and then adding a solution of potassium hydroxide (KOH) in water dropwise to the solution to form a yellow- colored precipitate. The heterogenous mixture containing the yellow precipitate can be heated under reflux till the mixture turns pink. Further, triphenylmethanol and p-toluenesulfonic acid monohydrate can be added to acetic anhydride, and stirred at room temperature for at least 3 hrs. Then, solid tetraketone can be added to the reaction mixture, and the mixture can be heated to 100 ºC for at least 1 hr. The heterogeneous mixture becomes clear. Upon cooling, yellow crystals appear and cam be collected by filtration, after which they can be washed carefully with acetic anhydride and ethanol to obtain bispyrylium ditosylate monomer. Thorpe North & Western, LLP Docket No.: 4917-002.PCT At a second step, the method can comprise dissolving the ditosylate monomer in a solvent to prepare a ditosylate monomer solution. In an embodiment, the solvent is selected from but not limited to methanol, acetonitrile and DMSO. Specifically, the solvent is selected depending upon the solubility of a salt containing a counter ion. In an embodiment, the proportion used of the ditosylate monomer is 1-100 gm%. In another embodiment, the proportion of the solvent being used in 1-100 gm%. In yet another embodiment, the ratio of the ditosylate monomer in a solvent is 1-100:100-1. At a third step, the method can comprise dissolving 5 to 20 equivalents of the salt containing the counter ion into the ditosylate monomer solution of the second step to form a mixture. The mixture is then stirred for a predefined time period ranging from 1 to 24 hrs. At a fourth step, the method can comprise pouring the mixture of the third step into a non-solvent and collecting the subsequent solid. Elemental analysis can be used to confirm the presence of the salt exchanged by elemental differences. In an embodiment, the non-solvent can be water. However, it may be evident to those skilled in the art to use any suitable non- solvent known in the art. In further examples, the ditosylate monomer ion can be exchanged with counterions to modify various properties. In one example, phosphorous based ions can be exchanged with the ditosylate monomer cations to increase flame retardancy, vary phosphorous content, and increase char yield. In another example, phosphorous based ions with short or long alkyl chains can be exchanged with ditosylate monomer cations to decrease brittleness and increase blending with commercial solids and polymers. In yet another example, phosphorous based ions with aromatic rings can be exchanged with ditosylate monomer cations to decrease brittleness and increase blending with commercial solids and polymers. In further examples, boron-based ions can be exchanged with the ditosylate monomer cations to increase flame retardancy and vary boron content. In a certain example, the boron- based ions can be exchanged with ditosylate monomer cations to increase char yield. In some examples, boron-based ions with short or long alkyl chains can be exchanged with the ditosylate monomer cations to decrease brittleness and increase blending with commercial solids and polymers. In other examples, boron-based ions with aromatic rings can be exchanged with the ditosylate monomer cations to decrease brittleness and increase blending with commercial solids and polymers. Thorpe North & Western, LLP Docket No.: 4917-002.PCT In still further examples, sulfur-based ions can be exchanged with the ditosylate monomer cations to increase flame retardancy and vary sulfur content. The sulfur-based ions can also be exchanged with the ditosylate monomer cations to increase char yield. In certain examples, sulfur-based ions with short or long alkyl chains can be exchanged with the ditosylate monomer cations to decrease brittleness and increase blending with commercial solids and polymers. In other examples, sulfur-based ions with aromatic rings can be exchanged with the ditosylate monomer cations to decrease brittleness and increase blending with commercial solids and polymers. In further examples, oxygen-based ions can be exchanged with the ditosylate monomer cations to increase flame retardancy and vary oxygen content. Oxygen-based ions can also be exchanged with ditosylate monomer cations to increase char yield. In certain examples, oxygen- based ions with short or long alkyl chains can be exchanged with the ditosylate monomer cations to decrease brittleness and increase blending with commercial solids and polymers. In further examples, oxygen-based ions with aromatic rings can be exchanged with the ditosylate monomer cations to decrease brittleness and increase blending with commercial solids and polymers. Some example monoanions that can be used for preparation of flame-retardant material in accordance with the present invention can be selected from but not limited to aromatic and aliphatic carbonates, halides, nitrates, dibasic phosphates, and the like. Example dianions that can be used in accordance with the present invention can be selected from but not limited to carbonates, sulfates, dibasic phosphates, boronates and the like. As explained above, any of these anions can be exchanged with the tosylate counterions of the ditosylate monomer or polymer. In yet another aspect, the present invention provides a method of preparation of the fire-retardant material using a bispyrylium ditosylate polymer as a base material. A dianion can be exchanged with the counterions of the ditosylate monomer or polymer. Dianions can include carbonates, sulfates, dibasic phosphates, boronates and the like. In an embodiment, the sulfur-based ions include but are not limited to sulfate (SO4)-2ions, bisulfate (HSO4)-1ions, thiosulfate (S2O3)-2ions, dithionite (S2O4)-2ions, metabisulfate (S2O5)-2ions, persulfate (S2O8)-2ions, methanesulfonate (CH3SO3)-1ions, dodecylsulfate (CH3(CH2)11OSO3)-1ions, or combinations thereof. Thorpe North & Western, LLP Docket No.: 4917-002.PCT In a preferred embodiment, the sulfur-based ions include bisulfate (HSO4)-1ions. In another preferred embodiment, the sulfur-based ions include dodecylsulfate (CH3(CH2)11OSO3)-1ions. In an embodiment, the phosphorous-based ions include but are not limited to monophosphate (H2PO4)-1ions, diphosphate (HPO4)-2ions, phosphate tri (PO4)3ions, tripolyphosphate (P3O10)-5ions, hypophosphite (HPO2)-2ions, pyrophosphate (P2O7)-4ions, dibasic pyrophosphate / dibasic (H2P2O7)-2ions, hexametaphosphate (NaPO3)n ions, or combinations thereof. In a preferred embodiment, the phosphorous-based ions include monophosphate (H2PO4)-1ions. In another preferred embodiment, the phosphorous-based ions include dibasic pyrophosphate (H2P2O7)-2ions. In an embodiment, the aromatic and aliphatic carbonate ions include but are not limited to benzoate (C6H5CO2)-1ions, acetate (CH3CO2)-1ions, formate (HCO2)-1ions, octanoate (CH3(CH2)6CO2)-1ions, citrate HOC(CO2)(CH2CO2)2-3ions, tartrate (C6H4O6)-2ions, gluconate (C6H11O7)-1ions, or combinations thereof. In a preferred embodiment, the aromatic and aliphatic carbonate ions include acetate (CH3CO2)-1ions. In another preferred embodiment, the aromatic and aliphatic carbonate ions include gluconate (C6H11O7)-1ions. In an embodiment, the nitrogen-based ions include but are not limited to Azide (N3)-1ions, Nitrate (NO3)-1ions, nitrite (NO2)-1ions, L-glutamate (C5H8NO4)-1ions, or combinations thereof. In a preferred embodiment, the nitrogen-based ions include Nitrate (NO3)-1ions. In another preferred embodiment, the nitrogen-based ions include gluconate L- glutamate (C5H8NO4)-1ions. In another embodiment, the silicon-based ion includes Metasilicate Na2O3Si ^ 9H2O ions. In another embodiment, the boron-based ion includes but are not limited to borate (B4O7)-2ions, perborate (BO3)-1ions, or combinations thereof. Thorpe North & Western, LLP Docket No.: 4917-002.PCT In yet another aspect, the present invention provides a method of preparation of the fire-retardant material using a bispyrylium ditosylate polymer as a base material. At first step, the method comprises preparing bispyrylium ditosylate monomer i.e. 4,4’-(1,4-Phenylene)-bis(2,6-diphenylpyrylium) ditosylate monomer. In an embodiment, the bispyrylium ditosylate monomer is prepared by first reacting terephthalaldehyde and acetophenone in ethanol and then adding a solution of potassium hydroxide (KOH) in water dropwise to the solution to form a yellow-colored precipitate. The heterogenous mixture containing the yellow precipitate is heated under reflux till the mixture turns pink. Further, triphenylmethanol and p-toluenesulfonic acid monohydrate are added to acetic anhydride, and stirred at room temperature for at least 3 hrs. Then, solid tetraketone is added to the reaction mixture, and the mixture is heated to 100ºC for at least 1 hr. The heterogeneous mixture becomes clear. Upon cooling, yellow crystals appear and are collected by filtration, after which they are washed carefully with acetic anhydride and ethanol to obtain bispyrylium ditosylate monomer. The monomer can then be polymerized with a diamine monomer through a ring transmutation polymerization reaction to form a ditosylate polymer. At second step, the method comprises dissolving the ditosylate polymer in a solvent to prepare a ditosylate polymer solution. In an embodiment, the solvent is selected from but not limited to methanol, acetonitrile and DMSO. Specifically, the solvent is selected depending upon the solubility of a salt containing a counter ion. In an embodiment, the proportion used of the ditosylate polymer is 1-100 gm%. In another embodiment, the proportion of the solvent being used in 1-100 gm%. In yet another embodiment, the ratio of the ditosylate polymer in the solvent is 1-100:100-1. At third step, the method comprises dissolving 5 to 20 equivalents of the salt containing the counter ion into the ditosylate polymer solution of the second step to form a mixture. The mixture is then stirred for a predefined time period ranging from 1 to 24 hrs. At fourth step, the method comprises pouring the mixture of the third step into a non- solvent and collecting the subsequent solid. Elemental analysis is used to confirm the present of salt exchanged by elemental differences. In an embodiment, the non-solvent is water. However, it may be evident to those skilled in the art to use any suitable non-solvent known in the art. This process can exchange a portion or all of the tosylate counterions in the polymer Thorpe North & Western, LLP Docket No.: 4917-002.PCT with new counterions from the salt. In various examples, the salt that is used can include an anion that can modify various properties of the polymer, such as flame retardancy, char yield, brittleness, blending ability with other polymers, and proportions of various elements in the polymer. Any of the example ions described above with respect to the counterion exchange of the ditosylate monomers can also be used for counterion exchange of the ditosylate polymers. Any of the various features and components of the systems described above can also be used in the methods described herein. Similarly, any equipment or features described in the methods can be incorporated in the systems described herein. While the forgoing examples are illustrative of the principles of the present invention in one or more particular applications, it will be apparent to those of ordinary skill in the art that numerous modifications in form, usage and details of implementation can be made without the exercise of inventive faculty, and without departing from the principles and concepts of the invention. Accordingly, it is not intended that the invention be limited, except as by the claims set forth below. Examples A polymer was prepared having the chemical structure shown in FIG. 8. In this structure, the n is an integer from 2 to about 100,000. The polymer included tosylate counterions, which are not shown in the figure. Samples of this polymer were then converted to a series of counterion-exchanged polymers using various counterion exchange processes and various salts having different anions. One set of samples were prepared by dissolving the salt in water and separately dissolving the polymer in a solvent. The polymer solution was then added to the water solution, causing the polymer to precipitate. In this method, the ion exchange occurs just before the polymer changes phase from dissolved to solid. The following salts were used with this method: sodium chloride, sodium metasilicate, sodium bisulfate, sodium acetate trihydrate, sodium dodecyl sulfate, inositol hexaphosphate, monopotassium phosphate, monosodium phosphate, and phytic acid. This method resulted in polymers having anions that originated from the salts exchanged for some or all of the tosylate anions in the original polymer. The polymers were tested using differential scanning calorimetry and thermogravimetric analysis. FIG.9 shows the Thorpe North & Western, LLP Docket No.: 4917-002.PCT differential scanning calorimetry results and FIG. 10 shows the thermogravimetric analysis results. A second set of polymer samples were prepared by mixing both the polymer and the salt into a solvent together. This solution was then added to water, causing the polymer to precipitate as a solid. In this method, the ion exchange occurs in the liquid phase of solvent where both the polymer and the salt are dissolved. This method was used with the following salts: sodium monododecyl phosphate and inositol hexaphosphate. The resulting polymers had anions that originated from the salts exchanged for some or all of the tosylate counterions of the original polymer. The polymers of this second set were analyzed using differential scanning calorimetry. The results of differential scanning calorimetry are shown in FIG.11. A polymer sample was prepared using a third method. This method included ball milling the polymer and the salt together for about 12 hours. In this example, the ion exchange occurs when the polymer contacts the salt in the ball mill. Inositol hexaphosphate was used as the salt in this method. The resulting polymer included phosphate anions exchanged for some or all of the tosylate anions that were present in the original polymer. This polymer was analyzed using differential scanning calorimetry. The results of the differential scanning calorimetry are shown in FIG.12. A fourth set of polymer samples were prepared using a fourth method. In this method, The polymer and the salt are melted together and the mixed with a carrier polymer (nylon) through extrusion. In this method, the ion exchange occurs when the polymer and salt are in the melted phase. The salts used with this method included: inositol hexaphosphate, monopotassium phosphate, ammonium phytate, diammonium phosphate, and monoammonium phosphate. The resulting polymers each included the anion originating from the respective salt exchanged for some or all of the tosylate counterions in the original polymer. The polymer formed using inositol hexaphosphate was analyzed using differential scanning calorimetry. The differential scanning calorimetry results are shown in FIG.13. Additional Enumerated Examples The invention described herein can include the following enumerated examples. Thorpe North & Western, LLP Docket No.: 4917-002.PCT 1. A polymer comprising pyridinium salt moieties, wherein the polymer has the following structure: wherein R2 and R7 are each negatively charged counterions; wherein R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; wherein R5 is any group comprising one or more carbon atoms; wherein R10 has the following structure: x an 2 to about 70; and wherein n is an integer from 2 to about 100,000. 2. A polymer comprising pyridinium salt moieties, wherein the polymer has the following structure: Thorpe North & Western, LLP Docket No.: 4917-002.PCT wherein R1 and R6 are each N; wherein at least a portion of R2 and R7 groups in the polymer are each negatively charged counterions selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus- containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof; wherein R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; wherein R5 and R10 are any group comprising one or more carbon atoms; and wherein n is an integer from 2 to about 100,000. 3. A polymer comprising pyridinium salt moieties, wherein the polymer has the following structure: wherein at least a portion of R2 and R7 groups in the polymer are each negatively charged counterions selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus- containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof; wherein R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; wherein R5 and R10 are any group comprising one or more carbon atoms and which are devoid of phosphorus atoms; and wherein n is an integer from 2 to about 100,000. Thorpe North & Western, LLP Docket No.: 4917-002.PCT 4. A flame-retardant polymer comprising pyridinium salt moieties, wherein the polymer has the following structure: wherein at least a portion of R2 and R7 groups in the polymer are each negatively charged flame-retardant counterions; wherein R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; wherein R5 and R10 are any group comprising one or more carbon atoms and which are devoid of phosphorus atoms; and wherein n is an integer from 2 to about 100,000. 5. A polymer mixture comprising a base polymer mixed with a flame-retardant polymeric additive, wherein the flame-retardant polymeric additive has the following structure: wherein R1 and R6 are each N; Thorpe North & Western, LLP Docket No.: 4917-002.PCT wherein at least a portion of R2 and R7 groups in the polymer are each negatively charged counterions selected to modulate compatibility of the flame-retardant polymeric additive with the base polymer; wherein R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; wherein R5 and R10 are any group comprising one or more carbon atoms; and wherein n is an integer from 2 to about 100,000. 6. A method of making a counterion-exchanged polymer, comprising: reacting a bispyrylium monomer comprising a first counterion with a diamine monomer using a ring-transmutation polymerization reaction to form a first polymer, wherein the diamine monomer is devoid of phosphorus atoms; dissolving the first polymer in a solvent; exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof; and recovering the first polymer with the second counterion as a counterion-exchanged polymer. 7. A method of making a counterion-exchanged polymer, comprising: dissolving a bispyrylium monomer comprising a first counterion in a solvent; exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof to form a counterion-exchanged bispyrylium monomer; and reacting the counterion-exchanged bispyrylium monomer with a diamine monomer using a ring-transmutation polymerization reaction to form a counterion-exchanged polymer, wherein the diamine monomer is devoid of phosphorus atoms. Thorpe North & Western, LLP Docket No.: 4917-002.PCT 8. A method of making a counterion-exchanged polymer, comprising: reacting a bispyrylium monomer comprising a first counterion with a diamine monomer using a ring-transmutation polymerization reaction to form a first polymer; dissolving the first polymer in a solvent; exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof; and recovering the first polymer with the second counterion as a counterion-exchanged polymer. 9. A method of making a counterion-exchanged polymer, comprising: dissolving a bispyrylium monomer comprising a first counterion in a solvent; exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof to form a counterion-exchanged bispyrylium monomer; and reacting the counterion-exchanged bispyrylium monomer with a diamine monomer using a ring-transmutation polymerization reaction to form a counterion-exchanged polymer. 10. The polymer, polymer mixture, or method of any of examples 1-44, wherein R5 is devoid of phosphorus atoms. 11. The polymer, polymer mixture, or method of any of examples 1-44, wherein R10 is devoid of phosphorus atoms. Thorpe North & Western, LLP Docket No.: 4917-002.PCT 12. The polymer, polymer mixture, or method of any of examples 1-44, wherein R5 comprises a phenylene group. 13. The polymer, polymer mixture, or method of any of examples 1-44, wherein at least one of R3, R4, R8, or R9 comprises a phenyl group. 14. The polymer, polymer mixture, or method of any of examples 1-44, wherein x is an integer from 2 to 5, or from 5 to 10, or from 30 to 35, or from 65 to 70. 15. The polymer, polymer mixture, or method of any of examples 1-44, wherein R2 and R7 are independently tosylate counterions or triflimide counterions. 16. The polymer, polymer mixture, or method of any of examples 1-44, wherein a first portion of the R2 and R7 groups are tosylate counterions or triflimide counterions, and wherein a second portion of the R2 and R7 groups have been exchanged for a different counterion. 17. The polymer, polymer mixture, or method of any of examples 1-44, wherein the first portion comprises from about 1% to about 33% of the R2 and R7 groups and the second portion comprises from about 67% to about 99% of the R2 and R7 groups. 18. The polymer, polymer mixture, or method of any of examples 1-44, wherein the different counterion comprises a negatively charged counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof. 19. The polymer, polymer mixture, or method of any of examples 1-44, wherein at least a portion of the R2 and R7 groups comprise a negatively charged counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof. Thorpe North & Western, LLP Docket No.: 4917-002.PCT 20. The polymer, polymer mixture, or method of any of examples 1-44, wherein at least a portion of the R2 and R7 groups comprise a negatively charged counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof. 21. The polymer, polymer mixture, or method of any of examples 1-44, wherein at least a portion of the R2 and R7 groups comprise dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof. 22. The polymer, polymer mixture, or method of any of examples 1-44, wherein at least a portion of the R2 and R7 groups comprise sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof. 23. The polymer, polymer mixture, or method of any of examples 1-44, wherein at least a portion of the R2 and R7 groups comprise benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarcosinate, stearate, or a combination thereof. 24. The polymer, polymer mixture, or method of any of examples 1-44, wherein at least a portion of the R2 and R7 groups comprise tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, tetrafluoroborate, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, Thorpe North & Western, LLP Docket No.: 4917-002.PCT bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof. 25. The polymer, polymer mixture, or method of any of examples 1-44, wherein R10 comprises at least one of the following structures: , wherein x is an integer from 2 to about 70. Thorpe North & Western, LLP Docket No.: 4917-002.PCT 26. The polymer, polymer mixture, or method of any of examples 1-44, wherein the base polymer comprises polyolefins, polyacrylonitriles, polystyrenes, polyamides, polyimides, polyethers, polyester, polycarbonates, polyurethanes, viscose rayon, cellulous acetate, epoxies, natural and synthetic rubbers, or a combination thereof. 27. The polymer, polymer mixture, or method of any of examples 1-44, wherein the mixture comprises from 50% to 99% of the base polymer and from about 1% to about 50% of the flame retardant polymeric additive. 28. The polymer, polymer mixture, or method of any of examples 1-44, wherein the exchanging is performed by dissolving the first polymer in a solvent and dissolving a salt comprising the second counterion in the solvent, then adding a non-solvent to precipitate the counterion- exchanged polymer. 29. The polymer, polymer mixture, or method of any of examples 1-44, wherein the exchanging is performed by dissolving the first polymer in a solvent and dissolving a salt comprising the second counterion in water, then adding the solvent with the dissolved first polymer to the water with the dissolved salt, thereby precipitating the counterion-exchanged polymer, wherein the solvent is a water-miscible solvent. 30. The polymer, polymer mixture, or method of any of examples 1-44, wherein the exchanging is performed by dissolving the first polymer in a solvent and passing the solvent with the dissolved first polymer through an ion-exchange column containing the second counterion. 31. The polymer, polymer mixture, or method of any of examples 1-44, wherein the exchanging is performed by dissolving the first polymer in a solvent and placing the solvent with the dissolved first polymer in contact with a dialysis membrane, and placing a solution comprising the second counterion in contact with an opposite side of the dialysis membrane. Thorpe North & Western, LLP Docket No.: 4917-002.PCT 32. The polymer, polymer mixture, or method of any of examples 1-44, wherein the exchanging is performed by milling the first polymer with a salt comprising the second counterion for a time sufficient to exchange at least a portion of the first counterion with the second counterion. 33. The polymer, polymer mixture, or method of any of examples 1-44, wherein the exchanging is performed by melting the first polymer and a salt comprising the second counterion and mixing the melted polymer and salt together. 34. The polymer, polymer mixture, or method of any of examples 1-44, wherein the first counterion comprises tosylate counterions or triflimide counterions. 35. The polymer, polymer mixture, or method of any of examples 1-44, wherein counterions in the counterion-exchanged polymer comprise from about 1% to about 33% of the first counterion and from about 67% to about 99% of the second counterion. 36. The polymer, polymer mixture, or method of any of examples 1-44, wherein the second counterion comprises dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof. 37. The polymer, polymer mixture, or method of any of examples 1-44, wherein the second counterion comprises sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof. 38. The polymer, polymer mixture, or method of any of examples 1-44, wherein the second counterion comprises benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, Thorpe North & Western, LLP Docket No.: 4917-002.PCT glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarcosinate, stearate, or a combination thereof. 39. The polymer, polymer mixture, or method of any of examples 1-44, wherein the second counterion comprises tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof. 40. The polymer, polymer mixture, or method of any of examples 1-44, wherein the diamine monomer comprises at least one of the following structures: , , Thorpe North & Western, LLP Docket No.: 4917-002.PCT wherein x is an integer from 2 to about 70. 41. The polymer, polymer mixture, or method of any of examples 1-44, wherein the exchanging is performed by dissolving a salt comprising the second counterion in the solvent, then adding a non-solvent to precipitate the counterion-exchanged bispyrylium monomer. 42. The polymer, polymer mixture, or method of any of examples 1-44, wherein the exchanging is performed by dissolving a salt comprising the second counterion in water, then adding the solvent with the dissolved bispyrylium monomer to the water with the dissolved salt, thereby precipitating the counterion-exchanged bispyrylium monomer, wherein the solvent is a water- miscible solvent. 43. The polymer, polymer mixture, or method of any of examples 1-44, wherein the exchanging is performed by passing the solvent with the dissolved bispyrylium monomer through an ion- exchange column containing the second counterion. 44. The polymer, polymer mixture, or method of any of examples 1-44, wherein the exchanging is performed by placing the solvent with the dissolved bispyrylium monomer in contact with a dialysis membrane, and placing a solution comprising the second counterion in contact with an opposite side of the dialysis membrane.

Claims

Thorpe North & Western, LLP Docket No.: 4917-002.PCT CLAIMS What is claimed is:

1. A polymer comprising pyridinium salt moieties, wherein the polymer has the following structure:wherein R2 and R7 are each negatively charged counterions; wherein R3, R4, R8, R9, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; wherein R5 is any group comprising one or more carbon atoms; wherein R10 has the following structure:wherein x is an integer from 2 to about 70; and wherein n is an integer from 2 to about 100,000.

2. The polymer of claim 1, wherein R5 is devoid of phosphorus atoms.

3. The polymer of claim 1, wherein R5 comprises a phenylene group.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 4. The polymer of claim 1, wherein at least one of R3, R4, R8, or R9 comprises a phenyl group.

5. The polymer of claim 1, wherein x is an integer from 2 to 5, or from 5 to 10, or from 30 to 35, or from 65 to 70.

6. The polymer of claim 1, wherein R2 and R7 are independently tosylate counterions or triflimide counterions.

7. The polymer of claim 1, wherein a first portion of the R2 and R7 groups are tosylate counterions or triflimide counterions, and wherein a second portion of the R2 and R7 groups have been exchanged for a different counterion.

8. The polymer of claim 7, wherein the first portion comprises from about 1% to about 33% of the R2 and R7 groups and the second portion comprises from about 67% to about 99% of the R2 and R7 groups.

9. The polymer of claim 7, wherein the different counterion comprises a negatively charged counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus- containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof.

10. The polymer of claim 1, wherein at least a portion of the R2 and R7 groups comprise a negatively charged counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof.

11. The polymer of claim 1, wherein at least a portion of the R2 and R7 groups comprise a negatively charged counterion selected from the group consisting of carboxylates, nitrates,Thorpe North & Western, LLP Docket No.: 4917-002.PCT nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof.

12. The polymer of claim 1, wherein at least a portion of the R2 and R7 groups comprise dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof.

13. The polymer of claim 1, wherein at least a portion of the R2 and R7 groups comprise sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof.

14. The polymer of claim 1, wherein at least a portion of the R2 and R7 groups comprise benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof.

15. The polymer of claim 1, wherein at least a portion of the R2 and R7 groups comprise tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, tetrafluoroborate, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof.

16. A polymer comprising pyridinium salt moieties, wherein the polymer has the following structure:Thorpe North & Western, LLP Docket No.: 4917-002.PCTwherein at least a portion of R2 and R7 groups in the polymer are each negatively charged counterions selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof; wherein R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; wherein R5 and R10 are any group comprising one or more carbon atoms; and wherein n is an integer from 2 to about 100,000.

17. The polymer of claim 16, wherein R5 is devoid of phosphorus atoms.

18. The polymer of claim 16, wherein R10 is devoid of phosphorus atoms.

19. The polymer of claim 16, wherein R5 comprises a phenylene group.

20. The polymer of claim 16, wherein at least one of R3, R4, R8, or R9 comprises a phenyl group.

21. The polymer of claim 16, wherein a first portion of the R2 and R7 groups are tosylate counterions or triflimide counterions, and wherein a second portion of the R2 and R7 groups are the negative charged counterions.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 22. The polymer of claim 21, wherein the first portion comprises from about 1% to about 33% of the R2 and R7 groups and the second portion comprises from about 67% to about 99% of the R2 and R7 groups.

23. The polymer of claim 16, wherein at least a portion of the R2 and R7 groups comprise dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof.

24. The polymer of claim 16, wherein at least a portion of the R2 and R7 groups comprise lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, dioctyl sulfosuccinate, 3- sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof.

25. The polymer of claim 16, wherein at least a portion of the R2 and R7 groups comprise benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof.

26. The polymer of claim 16, wherein at least a portion of the R2 and R7 groups comprise tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof.

27. The polymer of claim 16, wherein R10 comprises at least one of the following structures:Thorpe North & Western, LLP Docket No.: 4917-002.PCT , ,wherein x is an integer from 2 to about 70.

28. A polymer comprising pyridinium salt moieties, wherein the polymer has the following structure:Thorpe North & Western, LLP Docket No.: 4917-002.PCTwherein at least a portion of R2 and R7 groups in the polymer are each negatively charged counterions selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof; wherein R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; wherein R5 and R10 are any group comprising one or more carbon atoms and which are devoid of phosphorus atoms; and wherein n is an integer from 2 to about 100,000.

29. The polymer of claim 28, wherein R5 comprises a phenylene group.

30. The polymer of claim 28, wherein at least one of R3, R4, R8, or R9 comprises a phenyl group.

31. The polymer of claim 28, wherein a first portion of the R2 and R7 groups are tosylate counterions or triflimide counterions, and wherein a second portion of the R2 and R7 groups are the negative charged counterions.

32. The polymer of claim 31, wherein the first portion comprises from about 1% to about 33% of the R2 and R7 groups and the second portion comprises from about 67% to about 99% of the R2 and R7 groups.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 33. The polymer of claim 28, wherein at least a portion of the R2 and R7 groups comprise dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof.

34. The polymer of claim 28, wherein at least a portion of the R2 and R7 groups comprise sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof.

35. The polymer of claim 28, wherein at least a portion of the R2 and R7 groups comprise benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof.

36. The polymer of claim 28, wherein at least a portion of the R2 and R7 groups comprise tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof.

37. The polymer of claim 28, wherein R10 comprises at least one of the following structures: , ,Thorpe North & Western, LLP Docket No.: 4917-002.PCT or wherein x is an38. A flame-retardant polymer comprising pyridinium salt moieties, wherein the polymer has the following structure:wherein at least a portion of R2 and R7 groups in the polymer are each negatively charged flame-retardant counterions; wherein R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; wherein R5 and R10 are any group comprising one or more carbon atoms and which are devoid of phosphorus atoms; and wherein n is an integer from 2 to about 100,000.

39. The polymer of claim 38, wherein R5 comprises a phenylene group.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 40. The polymer of claim 38, wherein at least one of R3, R4, R8, or R9 comprises a phenyl group.

41. The polymer of claim 38, wherein a first portion of the R2 and R7 groups are tosylate counterions or triflimide counterions, and wherein a second portion of the R2 and R7 groups are the negative charged counterions.

42. The polymer of claim 41, wherein the first portion comprises from about 1% to about 33% of the R2 and R7 groups and the second portion comprises from about 67% to about 99% of the R2 and R7 groups.

43. The polymer of claim 38, wherein at least a portion of the R2 and R7 groups comprise dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof.

44. The polymer of claim 38, wherein at least a portion of the R2 and R7 groups comprise sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof.

45. The polymer of claim 38, wherein at least a portion of the R2 and R7 groups comprise benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof.

46. The polymer of claim 38, wherein at least a portion of the R2 and R7 groups comprise tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide,Thorpe North & Western, LLP Docket No.: 4917-002.PCT boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof.

47. The polymer of claim 38, wherein R10 comprises at least one of the following structures: , ,wherein x is an integer from 2 to about 70.

48. A polymer mixture comprising a base polymer mixed with a flame-retardant polymeric additive, wherein the flame-retardant polymeric additive has the following structure:Thorpe North & Western, LLP Docket No.: 4917-002.PCTwherein at least a portion of R2 and R7 groups in the polymer are each negatively charged counterions selected to modulate compatibility of the flame-retardant polymeric additive with the base polymer; wherein R3, R4, R8, R9, R11, R13, R14, R15, and R16 are each selected from the group consisting of H and groups comprising one or more carbon atoms; wherein R5 and R10 are any group comprising one or more carbon atoms; and wherein n is an integer from 2 to about 100,000.

49. The polymer mixture of claim 48, wherein R5 comprises a phenylene group.

50. The polymer mixture of claim 48, wherein at least one of R3, R4, R8, or R9 comprises a phenyl group.

51. The polymer mixture of claim 48, wherein the base polymer comprises polyolefins, polyacrylonitriles, polystyrenes, polyamides, polyimides, polyethers, polyester, polycarbonates, polyurethanes, viscose rayon, cellulous acetate, epoxies, natural and synthetic rubbers, or a combination thereof.

52. The polymer mixture of claim 48, wherein the mixture comprises from 50% to 99% of the base polymer and from about 1% to about 50% of the flame retardant polymeric additive.

53. The polymer mixture of claim 48, wherein a first portion of the R2 and R7 groups are tosylate counterions or triflimide counterions, and wherein a second portion of the R2 and R7 groups are the negative charged counterions.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 54. The polymer mixture of claim 53, wherein the first portion comprises from about 1% to about 33% of the R2 and R7 groups and the second portion comprises from about 67% to about 99% of the R2 and R7 groups.

55. The polymer mixture of claim 48, wherein at least a portion of the R2 and R7 groups comprise dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof.

56. The polymer mixture of claim 48, wherein at least a portion of the R2 and R7 groups comprise sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof.

57. The polymer mixture of claim 48, wherein at least a portion of the R2 and R7 groups comprise benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof.

58. The polymer mixture of claim 48, wherein at least a portion of the R2 and R7 groups comprise tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof.

59. The polymer of claim 48, wherein R10 comprises at least one of the following structures:Thorpe North & Western, LLP Docket No.: 4917-002.PCT , ,wherein x is an integer from 2 to about 70.

60. A method of making a counterion-exchanged polymer, comprising: reacting a bispyrylium monomer comprising a first counterion with a diamine monomer using a ring-transmutation polymerization reaction to form a first polymer, wherein the diamine monomer is devoid of phosphorus atoms;Thorpe North & Western, LLP Docket No.: 4917-002.PCT exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof; and recovering the first polymer with the second counterion as a counterion-exchanged polymer.

61. The method of claim 60, wherein the exchanging is performed by dissolving the first polymer in a solvent and dissolving a salt comprising the second counterion in the solvent, then adding a non-solvent to precipitate the counterion-exchanged polymer.

62. The method of claim 60, wherein the exchanging is performed by dissolving the first polymer in a solvent and dissolving a salt comprising the second counterion in water, then adding the solvent with the dissolved first polymer to the water with the dissolved salt, thereby precipitating the counterion-exchanged polymer, wherein the solvent is a water- miscible solvent.

63. The method of claim 60, wherein the exchanging is performed by dissolving the first polymer in a solvent and passing the solvent with the dissolved first polymer through an ion- exchange column containing the second counterion.

64. The method of claim 60, wherein the exchanging is performed by dissolving the first polymer in a solvent and placing the solvent with the dissolved first polymer in contact with a dialysis membrane, and placing a solution comprising the second counterion in contact with an opposite side of the dialysis membrane.

65. The method of claim 60, wherein the exchanging is performed by milling the first polymer with a salt comprising the second counterion for a time sufficient to exchange at least a portion of the first counterion with the second counterion.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 66. The method of claim 60, wherein the exchanging is performed by melting the first polymer and a salt comprising the second counterion and mixing the melted polymer and salt together.

67. The method of claim 60, wherein the first counterion comprises tosylate counterions or triflimide counterions.

68. The method of claim 60, wherein counterions in the counterion-exchanged polymer comprise from about 1% to about 33% of the first counterion and from about 67% to about 99% of the second counterion.

69. The method of claim 60, wherein the second counterion comprises dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2- ethylehexyl) hydrogen phosphate, or a combination thereof.

70. The method of claim 60, wherein the second counterion comprises sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof.

71. The method of claim 60, wherein the second counterion comprises benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof.

72. The method of claim 60, wherein the second counterion comprises tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide,Thorpe North & Western, LLP Docket No.: 4917-002.PCT bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof.

73. The method of claim 60, wherein the diamine monomer comprises at least one of the following structures: , ,wherein x is an integer from 2 to about 70.

74. A method of making a counterion-exchanged polymer, comprising: dissolving a bispyrylium monomer comprising a first counterion in a solvent; exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-Thorpe North & Western, LLP Docket No.: 4917-002.PCT2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, sulfonates, and combinations thereof to form a counterion-exchanged bispyrylium monomer; and reacting the counterion-exchanged bispyrylium monomer with a diamine monomer using a ring-transmutation polymerization reaction to form a counterion-exchanged polymer, wherein the diamine monomer is devoid of phosphorus atoms.

75. The method of claim 74, wherein the exchanging is performed by dissolving a salt comprising the second counterion in the solvent, then adding a non-solvent to precipitate the counterion-exchanged bispyrylium monomer.

76. The method of claim 74, wherein the exchanging is performed by dissolving a salt comprising the second counterion in water, then adding the solvent with the dissolved bispyrylium monomer to the water with the dissolved salt, thereby precipitating the counterion-exchanged bispyrylium monomer, wherein the solvent is a water-miscible solvent.

77. The method of claim 74, wherein the exchanging is performed by passing the solvent with the dissolved bispyrylium monomer through an ion-exchange column containing the second counterion.

78. The method of claim 74, wherein the exchanging is performed by placing the solvent with the dissolved bispyrylium monomer in contact with a dialysis membrane, and placing a solution comprising the second counterion in contact with an opposite side of the dialysis membrane.

79. The method of claim 74, wherein the first counterion comprises tosylate counterions or triflimide counterions.

80. The method of claim 74, wherein counterions in the counterion-exchanged polymer comprise from about 1% to about 33% of the first counterion and from about 67% to about 99% of the second counterion.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 81. The method of claim 74, wherein the second counterion comprises dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2- ethylehexyl) hydrogen phosphate, or a combination thereof.

82. The method of claim 74, wherein the second counterion comprises sulfonate, dodecyl sulfate, lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, perfluorooctanesulfonate, perfluorobutanesulfonate, dioctyl sulfosuccinate, dodecylbenzenesulfonate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof.

83. The method of claim 74, wherein the second counterion comprises benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof.

84. The method of claim 74, wherein the second counterion comprises tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 85. The method of claim 74, wherein the diamine monomer comprises at least one of the following structures: , ,wherein x is an integer from 2 to about 70.

86. A method of making a counterion-exchanged polymer, comprising: reacting a bispyrylium monomer comprising a first counterion with a diamine monomer using a ring-transmutation polymerization reaction to form a first polymer; exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof; andThorpe North & Western, LLP Docket No.: 4917-002.PCT recovering the first polymer with the second counterion as a counterion-exchanged polymer.

87. The method of claim 86, wherein the exchanging is performed by dissolving the first polymer in a solvent and dissolving a salt comprising the second counterion in the solvent, then adding a non-solvent to precipitate the counterion-exchanged polymer.

88. The method of claim 86, wherein the exchanging is performed by dissolving the first polymer in a solvent and dissolving a salt comprising the second counterion in water, then adding the solvent with the dissolved first polymer to the water with the dissolved salt, thereby precipitating the counterion-exchanged polymer, wherein the solvent is a water- miscible solvent.

89. The method of claim 86, wherein the exchanging is performed by dissolving the first polymer in a solvent and passing the solvent with the dissolved first polymer through an ion- exchange column containing the second counterion.

90. The method of claim 86, wherein the exchanging is performed by dissolving the first polymer in a solvent and placing the solvent with the dissolved first polymer in contact with a dialysis membrane, and placing a solution comprising the second counterion in contact with an opposite side of the dialysis membrane.

91. The method of claim 86, wherein the exchanging is performed by milling the first polymer with a salt comprising the second counterion for a time sufficient to exchange at least a portion of the first counterion with the second counterion.

92. The method of claim 86, wherein the exchanging is performed by melting the first polymer and a salt comprising the second counterion and mixing the melted polymer and salt together.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 93. The method of claim 86, wherein the first counterion comprises tosylate counterions or triflimide counterions.

94. The method of claim 86, wherein counterions in the counterion-exchanged polymer comprise from about 1% to about 33% of the first counterion and from about 67% to about 99% of the second counterion.

95. The method of claim 86, wherein the second counterion comprises dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2- ethylehexyl) hydrogen phosphate, or a combination thereof.

96. The method of claim 86, wherein the second counterion comprises lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof.

97. The method of claim 86, wherein the second counterion comprises benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof.

98. The method of claim 86, wherein the second counterion comprises tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl)borate, or a combination thereof.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 99. The method of claim 86, wherein the diamine monomer comprises at least one of the following structures: , ,wherein x is an integer from 2 to about 70.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 100. A method of making a counterion-exchanged polymer, comprising: dissolving a bispyrylium monomer comprising a first counterion in a solvent; exchanging the first counterion with a second counterion selected from the group consisting of carboxylates, nitrates, nitrites, azides, metasilicates, tetraborate, perborates, boronates, oxalatoborates, metaborates, phosphorus-containing anions, halides, sulfates, SO4-2, HSO4-1, thiosulfate, dithionite, metabisulfite, persulfate, methanesulfonate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, and combinations thereof to form a counterion-exchanged bispyrylium monomer; and reacting the counterion-exchanged bispyrylium monomer with a diamine monomer using a ring-transmutation polymerization reaction to form a counterion-exchanged polymer.

101. The method of claim 100, wherein the exchanging is performed by dissolving a salt comprising the second counterion in the solvent, then adding a non-solvent to precipitate the counterion-exchanged bispyrylium monomer.

102. The method of claim 100, wherein the exchanging is performed by dissolving a salt comprising the second counterion in water, then adding the solvent with the dissolved bispyrylium monomer to the water with the dissolved salt, thereby precipitating the counterion-exchanged bispyrylium monomer, wherein the solvent is a water-miscible solvent.

103. The method of claim 100, wherein the exchanging is performed by passing the solvent with the dissolved bispyrylium monomer through an ion-exchange column containing the second counterion.

104. The method of claim 100, wherein the exchanging is performed by placing the solvent with the dissolved bispyrylium monomer in contact with a dialysis membrane, and placing a solution comprising the second counterion in contact with an opposite side of the dialysis membrane.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 105. The method of claim 100, wherein the first counterion comprises tosylate counterions or triflimide counterions.

106. The method of claim 100, wherein counterions in the counterion-exchanged polymer comprise from about 1% to about 33% of the first counterion and from about 67% to about 99% of the second counterion.

107. The method of claim 100, wherein the second counterion comprises dihydrogen phosphate, hydrogen phosphate, orthophosphate, tripolyphosphate, hypophosphite, a phosphinate, pyrophosphate, pyrophosphate dibasic, hexametaphosphate, inositol hexaphosphate, bis(2-ethylehexyl) hydrogen phosphate, or a combination thereof.

108. The method of claim 100, wherein the second counterion comprises lauryl ether sulfate, laureth sulfate, myreth sulfate, pareth sulfate, dioctyl sulfosuccinate, 3-sulfopropyl ethoxylate laurylphenyl ether, sulfate, bisulfate, thiosulfate, dithionite, metabisulfate, persulfate, methanesulfonate, or a combination thereof.

109. The method of claim 100, wherein the second counterion comprises benzoate, acetate, formate, octanoate, citrate, tartrate, gluconate, glutamate, decanoate, laurate, oleate, linoleate, glyceryl monocaprate, glycerol monolaurate, elaidate, linolenate, lauroyl sarconsinate, stearate, or a combination thereof.

110. The method of claim 100, wherein the second counterion comprises tetraborate, perborate, boronate, oxalatoborate, metaborate, tris pentafluorophenyl borane, bis(oxalate) borate, difluoro(oxolato)borate, borohydride, boron nitride, butylboronate, trimethyl borate, pyridine boron trifluoride, boron trifluoride, boron phosphate, boron carbide, boric acid, boron oxide, bis(malonato)borate, bis(salicylate)borate, bis(mandelato)borate, tetra(p-tolyl) borate, or a combination thereof.Thorpe North & Western, LLP Docket No.: 4917-002.PCT 111. The method of claim 100, wherein the diamine monomer comprises at least one of the following structures: , ,Thorpe North & Western, LLP Docket No.: 4917-002.PCT wherein x is an integer from 2 to about 70.

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