Conjugated polymer fiber, preparation and use thereof

A method of preparing a conjugated polymer fiber, comprising:

• electrospinning a solution consisting of a solvent and an intrinsically conductive polymer precursor to form a fiber;
• and
• subsequently, crosslinking the intrinsically conductive polymer precursor by chemical solid-state oxidation or electrochemical solid-state oxidation to form a conjugated polymer fiber, wherein the intrinsically conductive polymer precursor comprises the ring opening metathesis polymerization product of a thiophene-containing norbornylene compound, wherein the thiophene-containing norbornylene compound is (bicyclo[2.2.1]hept-5-en-2-yl)methyl 2-(2,5-di(thiophen-3-yl)thiophen-3-yl)acetate, ((bicyclo[2.2.1]hept-5-en-2-yl)2-(2,5-di(thiophen-3-yl)thiophen-3-yl)acetate), or a combination comprising at least one of the foregoing thiophene-containing norbornylene compounds,
• optionally further comprising polymerizing the thiophene-containing norbornylene compound in the presence of (bicyclo[2.2.1]hept-5-en-2-yl)methyl acetate), ((bicyclo[2.2.1]hept-5-en-2-yl)acetate), ((bicyclo[2.2.1]hept-5-en-2-yl)acrylate), ((bicyclo[2.2.1]hept-5-en-2-yl)methacrylate), or a combination comprising at least one of the foregoing, wherein the acetate is optionally substituted with an alkyl, haloalkyl, or aryl group.

A conjugated polymer fiber prepared by the method comprising

• electrospinning a solution consisting of a solvent and an intrinsically conductive polymer precursor to form a fiber;
• and
• subsequently, crosslinking the intrinsically conductive polymer precursor by chemical solid-state oxidation or electrochemical solid-state oxidation to form a conjugated polymer fiber,
• wherein the conjugated polymer fiber has a diameter of about 1 to about 500 nanometers, and wherein the intrinsically conductive polymer precursor comprises a polynorbornylene according to the structure (XLII), (XLIII), (XLIV), (XLV), (XLVI) or (XLVII):
• wherein k is about 10 to about 3000;
• L is an ester, amide, carbamate, carbonate, ether, thioether, amine, alkylene, or arylene linking group;
• each Q is independently 3,4-ethylenedioxythiophene, 3,4-propylenedioxythiophene, 3,4-propylenedithiathiophene, 3,4-ethylenedithiathiophene, isathianaphthene, pyridothiophene, pyrizinothiophene, pyrrole, 3,4-ethylenedioxypyrrole, 3,4-ethylenedithiinopyrrole, 3,4-propylenedioxypyrrole, 3,4-propylenedithiinopyrrole, aniline, thionapthene, benzofuran, polyindole, dibenzothiophene, dibenzofuran, carbazole, bifuran, bipyrrole, thienothiophene, thienofuran, thienopyrrole, furanylpyrrole, furanylfuran, pyyrolylpyrrole, thieno[3,4-b]thiophene, thieno[3,4-b]furan, terfuran, or terpyrrole, wherein the foregoing are optionally substituted with alkyl, alkoxy, haloalkyl, haloalkoxy, or aryl substituent;
• wherein k is about 10 to about 3000;
• b is about 1 to about 3000;
• L is an ester, amide, carbamate, carbonate, ether, thioether, amine, alkylene, or arylene linking group;
• each Q is independently 3,4-ethylenedioxythiophene, 3,4-propylenedioxythiophene, 3,4-propylenedithiathiophene, 3,4-ethylenedithiathiophene, isathianaphthene, pyridothiophene, pyrizinothiophene, pyrrole, 3,4-ethylenedioxypyrrole, 3,4-ethylenedithiinopyrrole, 3,4-propylenedioxypyrrole, 3,4-propylenedithiinopyrrole, aniline, thionapthene, benzofuran, polyindole, dibenzothiophene, dibenzofuran, carbazole, bifuran, bipyrrole, thienothiophene, thienofuran, thienopyrrole, furanylpyrrole, furanylfuran, pyyrolylpyrrole, thieno[3,4-b]thiophene, thieno[3,4-b]furan, terfuran, or terpyrrole, wherein the foregoing are optionally substituted with alkyl, alkoxy, haloalkyl, haloalkoxy, or aryl substituent;
• each Y1 is independently hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, aryl, or alkylacetate;
• wherein k is about 10 to about 3000;
• b is about 1 to about 3000;
• q is about 1 to about 3000;
• each L and L1 is an ester, amide, carbamate, carbonate, ether, thioether, amine, alkylene, or arylene linking group;
• each Q is independently 3,4-ethylenedioxythiophene, 3,4-propylenedioxythiophene, 3,4-propylenedithiathiophene, 3,4-ethylenedithiathiophene, isathianaphthene, pyridothiophene, pyrizinothiophene, pyrrole, 3,4-ethylenedioxypyrrole, 3,4-ethylenedithiinopyrrole, 3,4-propylenedioxypyrrole, 3,4-propylenedithiinopyrrole, aniline, thionapthene, benzofuran, polyindole, dibenzothiophene, dibenzofuran, carbazole, bifuran, bipyrrole, thienothiophene, thienofuran, thienopyrrole, furanylpyrrole, furanylfuran, pyyrolylpyrrole, thieno[3,4-b]thiophene, thieno[3,4-b]furan, terfuran, or terpyrrole, wherein the foregoing are optionally substituted with alkyl, alkoxy, haloalkyl, haloalkoxy, or aryl substituent;
• each Y1 is independently hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, aryl, or alkylacetate;
• and
• each Z is independently vinyl, acryloyl, methacryloyl, acrylamido, or methacrylamido.

A conjugated polymer fiber prepared by the method comprising

• electrospinning a solution consisting of a solvent and an intrinsically conductive polymer precursor to form a fiber;
• and
• subsequently, crosslinking the intrinsically conductive polymer precursor by chemical solid-state oxidation or electrochemical solid-state oxidation to form a conjugated polymer fiber,
• wherein the conjugated polymer fiber has a diameter of about 1 to about 500 nanometers, and wherein the intrinsically conductive polymer precursor comprises the ring opening metathesis polymerization product of a thiophene-containing norbornylene compound, wherein the thiophene-containing norbornylene compound is (bicyclo[2.2.1]hept-5-en-2-yl)methyl 2-(2,5-di(thiophen-3-yl)thiophen-3-yl)acetate, ((bicyclo[2.2.1]hept-5-en-2-yl) 2-(2,5-di(thiophen-3-yl)thiophen-3-yl)acetate), or a combination comprising at least one of the foregoing thiophene-containing norbornylene compounds,
• optionally further comprising polymerizing the thiophene-containing norbornylene compound in the presence of (bicyclo[2.2.1]hept-5-en-2-yl)methyl acetate), ((bicyclo[2.2.1]hept-5-en-2-yl)acetate), ((bicyclo[2.2.1]hept-5-en-2-yl)acrylate), ((bicyclo[2.2.1]hept-5-en-2-yl)methacrylate), or a combination comprising at least one of the foregoing, wherein the acetate is optionally substituted with an alkyl, haloalkyl, or aryl group.