Polymeric ionic liquid—assisted polymerization for soluble polyaniline nanofibers

Abstract

To enhance the solubility of polyanilines (PANI), polymeric ionic liquid (PIL) was introduced into the polymerization synthesis of PANI with various proportions. The structure and properties of the modified PANIs were characterized by ¹H NMR, Fourier transform infrared spectroscopy, thermogravimetric analysis, ultraviolet-visible spectrum, etc. It was found that the obtained PANIs doped with PILs were soluble in various organic solvents such as N,N-dimethyl formamide and acetonitrile. Compared with the pure PANI, the PANIs doped by PILs showed remarkable solubility and their chemical structure and conductivity kept integrated.

Graphical abstract

Keywords

polyaniline / polymeric ionic liquid / doping / solubility

References

[1] Jacobo S E, Aphesteguy J C, Anton R L, Schegoleva N N, Kurlyandskaya G V. Influence of the preparation procedure on the properties of polyaniline based magnetic composites. European Polymer Journal, 2007, 43(4): 1333–1346

[2] Bai S L, Zhao Y B, Sun J H, Tian Y, Luo R X, Li D Q, Chen A F. Ultrasensitive room temperature NH₃ sensor based on a graphene-polyaniline hybrid loaded on PET thin film. Chemical Communications, 2015, 51(35): 7524–7527

[3] Wang L L, Huang H, Xiao S H, Cai D P, Liu Y, Liu B, Wang D D, Wang C X, Li H, Wang Y R, Li Q, Wang T. Enhanced sensitivity and stability of room-temperature NH₃ sensors using core-shell CeO₂ nanoparticles@cross-linked PANI with p-n heterojunctions. ACS Applied Materials & Interfaces, 2014, 6(16): 14131–14140

[4] Hino T, Namiki T, Kuramoto N. Synthesis and characterization of novel conducting composites of polyaniline prepared in the presence of sodium dodecylsulfonate. Synthetic Metals, 2006, 156(21): 1327–1332

[5] Fahmy A, Eisa W H, Yosef M, Hassan A. Ultra-thin films of poly(acrylic acid)/silver nanocomposite coatings for antimicrobial applications. Journal of Spectroscopy, 2016, 5: 1–11

[6] Anisha B S, Biswas R, Chennazhi K P, Jayakumar R. Chitosan-hyaluronic acid/nano silver composite sponges for drug resistant bacteria infected diabetic wounds. International Journal of Biological Macromolecules, 2013, 62(11): 310–320

[7] Nateghi M R, Shateri-Khalilabad M. Silver nanowire-functionalized cotton fabric. Carbohydrate Polymers, 2015, 117(1): 160–168

[8] Palaniappan S, John A. Polyaniline materials by emulsion polymerization pathway. Progress in Polymer Science, 2008, 33(7): 732–758

[9] Patil A O, Heeger A J, Wudl F. Optical properties of conducting polymers. Chemical Reviews, 1988, 88(1): 183–200

[10] Bilal S, Gul S, Holze R, Shah A H A. Shah. An impressive emulsion polymerization route for the synthesis of highly soluble and conducting polyaniline salts. Synthetic Metals, 2015, 206: 131–144

[11] Cao Z F, Xia Y Q, Chen C. Fabrication of novel ionic liquids-doped polyaniline as lubricant additive for anti-corrosion and tribological properties. Tribology International, 2018, 120: 446–454

[12] Urbach B, Korbakov N, Bar-David Y, Yitzchaik S, Sa’Ar A. Composite structures of polyaniline and mesoporous silicon: Electrochemistry, optical and transport properties. Journal of Physical Chemistry C, 2007, 111(44): 16586–16592

[13] Harlev E, Gulakhmedova T, Rubinovich I, Aizenshtein G. A new method for the preparation of conductive polyaniline solutions: Application to liquid crystal devices. Advanced Materials, 1996, 8(12): 994–997

[14] Dong J Q, Shen Q. Enhancement in solubility and conductivity of polyaniline with lignosulfonate modified carbon nanotube. Journal of Polymer Science. Part B, Polymer Physics, 2010, 47(20): 2036–2046

[15] Ayad M, El-Hefnawy G, Zaghlol S. Facile synthesis of polyaniline nanoparticles; its adsorption behavior. Chemical Engineering Journal, 2013, 217(2): 460–465

[16] Kinlen P J, Frushour B G, Ding Y, Menon V. Synthesis and characterization of organically soluble polyaniline and polyaniline block copolymers. Synthetic Metals, 1999, 101(1): 758–761

[17] Wang Y, Chen K, Li T, Li H M, Zeng R C, Zhang R L, Gu Y J, Ding J X, Liu H Q. Soluble polyaniline nanofibers prepared via surfactant-free emulsion polymerization. Synthetic Metals, 2014, 198: 293–299

[18] Calheiros L F, Soares B G, Barra G M O, Livi S. Ionic liquid—assisted emulsion polymerization of aniline in organic medium. Materials Chemistry and Physics, 2016, 179: 194–203

[19] Cao Y, Smith P, Heeger A J. Counter-ion induced processibility of conducting polyaniline and of conducting polyblends of polyaniline in bulk polymers. Synthetic Metals, 1992, 48(1): 91–97

[20] Ho K. Effect of phenolic based polymeric secondary dopants on polyaniline. Synthetic Metals, 2002, 126(2): 151–158

[21] Ouyang J. Recent advances of intrinsically conductive polymers. Acta Physico-Chimica Sinica, 2018, 34(11): 1211–1220

[22] Deb K, Sarkar K, Bera A, Debnath A, Saha B. Coupled polaron-electron charge transport in graphite functionalized polyaniline on cellulose: Metal free flexible p-type semiconductor. Synthetic Metals, 2018, 245: 96–101

[23] Yuan J, Antonietti M. Poly(ionic liquid)s: Polymers expanding classical property profiles. Polymer, 2011, 52(7): 1469–1482

[24] Yuan J, Mecerreyes D, Antonietti M. Poly(ionic liquid)s: An update. Progress in Polymer Science, 2013, 38(7): 1009–1036

[25] Marcilla R, Curri M L, Cozzoli P D, Martínez M T, Loinaz I, Grande H, Pomposo J A, Mecerreyes D. Nano-objects on a round trip from water to organics in a polymeric ionic liquid vehicle. Small, 2006, 2(4): 507–512

[26] Schüler D, Kerscher B, Beckert F, Thomann R, Mülhaupt R. Hyperbranched polymeric ionic liquids with onion-like topology as transporters and compartmentalized systems. Angewandte Chemie International Edition, 2013, 52(1): 455–458

[27] Bellayer S, Gilman J W, Eidelman N, Bourbigot S, Flambard X, Fox D M, Long H C, Trulove P C. Preparation of homogeneously dispersed multiwalled carbon nanotube/polystyrene nanocomposites via melt extrusion using trialkyl imidazolium compatibilizer. Advanced Functional Materials, 2010, 15(6): 910–916

[28] Kim T Y, Lee H W, Kim J E, Suh K S. Synthesis of phase transferable graphene sheets using ionic liquid polymers. ACS Nano, 2010, 4(3): 1612–1618

[29] Zhao H L, Yu Y T, Li Z H, Luo B, Wang X H, Wang Y P, Xia Y M. Linear polymeric ionic liquids as phase-transporters for both cationic and anionic dyes with synergic effects. Polymer Chemistry, 2015, 6(39): 7060–7068

[30] Fabio R, Do N G M, Santos P S. Dissolution and doping of polyaniline emeraldine base in imidazolium ionic liquids investigated by spectroscopic techniques. Macromolecular Rapid Communications, 2010, 28(5): 666–669

[31] Calheiros L F, Soares B G, Barra G M O, Livi S. Ionic liquid-assisted emulsion polymerization of aniline in organic medium. Materials Chemistry and Physics, 2016, 179: 194–203

[32] Zhang K, Zhang L L, Zhao X S, Wu J. Graphene/polyaniline nanofiber composites as supercapacitor electrodes. Chemistry of Materials, 2010, 22(4): 1392–1401

[33] Pernak J, Smiglak M, Griffin S T, Hough W L, Wilson T B, Pernak A, Zabielska-Matejuk J, Fojutowski A, Kitad K, Rogers R D. Long alkyl chain quaternary ammonium-based ionic liquids and potential applications. Green Chemistry, 2006, 8(9): 798–806

[34] Vaidya S G, Rastogi S, Aguirre A. Surfactant assisted processable organic nanocomposite dispersions of polyaniline-single wall carbon nanotubes. Synthetic Metals, 2010, 160(1): 134–138

[35] Pouget J P, Jozefowicz M E, Epstein A J, Tang X, MacDiarmid A G. X-ray structure of polyaniline. Macromolecules, 1991, 24(3): 779–789

[36] Zhang Z, Wan M, Wei Y. Highly crystalline polyaniline nanostructures doped with dicarboxylic acids. Advanced Functional Materials, 2010, 16(8): 1100–1104

[37] Fu X Z, Liang Y, Wu R T, Shen J H, Chen Z D, Chen Y W, Wang Y P, Xia Y M. Conductive core-sheath calcium alginate/graphene composite fibers with polymeric ionic liquids as an intermediate. Carbohydrate Polymers, 2019, 206: 328–335

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