Abstract
Poly(p-phenylene/pyrrole) (PPP-PPY) films were electrochemically synthesised on transparent indium-tin-oxide-covered glass (ITO) electrodes. The presence of two monomers, p-phenylene and pyrrole, in the polymerisation medium facilitated the synthesis process, yielding electroactive, uniform and stable films. In order to obtain materials with improved quality, PPP, PPY and PPP-PPY films were prepared in a mild, dry atmosphere. The morphological, electrochemical and optical properties were compared for different films obtained by varying the number of cycles with and without controlling humidity.
Similar content being viewed by others
References
Aeiyach, S., & Lacaze, P. C. (1989). Electropolymerization of benzene and biphenyl in organic media: Influence of different parameters (solvent, water, acidity, salt) on the formation of polyparaphenylene films (PPP). Journal of Polymer Science Part A: Polymer Chemistry, 27 515–526. DOI: 10.1002/pola.1989.080270212.
Arslan, A., & Hur, E. (2014). Electrochemical storage properties of polyaniline-, poly(N-methylaniline)-, and poly(N-ethylaniline)-coated pencil grafite electrodes. Chemical Papers, 68 504–515. DOI: 10.2478/s11696-013-0475-9.
Brédas, J. L., Chance, R. R., Silbey, R., Nicolas, G., & Durand, P. (1982). Valence effective hamiltonian study of the electronic structure of poly(p-phenylene) and poly(p-phenylene sulfide). The Journal of Chemical Physics, 77 371–378. DOI: 10.1063/1.443615.
Descroix, S., Hallias, G., Lagrost, C., & Pinson, J. (2013). Regular poly(para-phenylene) films bound to gold surfaces through the electrochemical reduction of diazonium salts followed by electropolymerization in an ionic liquid. Electrochimica Acta, 106 172–180. DOI: 10.1016/j.electacta.2013.05.063.
Fauvarque, J. F., Petit, M. A., Pfluger, F., Jutand, A., Chevrot, C., & Troupel, M. (1983). Preparation of poly(1,4-phenylene) by nickel(0) complex catalyzed electropolymerization. Macromolecular Rapid Communications, 4 455–457. DOI: 10.1002/marc.1983.030040703.
Goldenberg, L. M., Aeiyach, S., & Lacaze, P. C. (1992a). Electropolymerization of benzene in a two-phase benzene/acid system: comparative study in strong proton acid and superacid media. Journal of Electroanalytical Chemistry, 327 173–184. DOI: 10.1016/0022-0728(92)80145-t.
Goldenberg, L. M., Aeiyach, S., & Lacaze, P. C. (1992b). Electropolymerization of benzene in a two-phase strong proton acid-benzene system. Synthetic Metals, 51 343–348. DOI: 10.1016/0379-6779(92)90289-u.
Kovacic, P., & Oziomek, J. (1964). p-Polyphenyl from benzene-Lewis acid catalyst-oxidant. Reaction scope and investigation of the benzene-aluminum chloride-cupric system. The Journal of Organic Chemistry, 29 100–104. DOI: 10.1021/jo01024a023.
Lee, H. J., Cui S. Y., & Park, S. M. (2001). Electrochemistry of conductive polymers. XXV. Electrochemical preparation and characterization of poly(p-phenylenes) from biphenyl and p-terphenyl. Journal of the Electrochemical Society, 148, D139–D145. DOI: 10.1149/1.1401080.
Mailhe-Randolph, C., & Desilvestro, J. (1989). Morphology of electropolymerized aniline films modified by para-phenylenediamine. Journal of Electroanalytical Chemistry, 262 289–295. DOI: 10.1016/0022-0728(89)80030-0.
Mazurkiewicz, J. H., Innis, P. C., Wallace, G. G., MacFarlane, D. R., & Forsyth, M. (2003). Conducting polymer electrochemistry in ionic liquids. Synthetic Metals, 135–136 31–32. DOI: 10.1016/s0379-6779(02)00688-4.
Rault-Berthelot, J., & Tahri-Hassani, J. (1996). Anodic oxidation of biphenyl and p-terphenyl in dry CH2Cl2 +0.2 M Bu4NF4. Towards poly(p-phenylene) possessing stable and reversible p- and n-doping processes. Journal of Electroanalytical Chemistry, 408 247–256. DOI: 10.1016/0022-0728(95)04452-3.
Soares, J. C., Foschini, M., Eiras, C., Sanches, E. A., & Gonçalves, D. (2014). Electrosynthesis and optical characterization of poly(p-phenylene), polypyrrole and poly(p-phenylene)-polypyrrole films. Materials Research, 17 332–337. DOI: 10.1590/s1516-14392014005000008.
Soubiran, P., Aeiyach, S., & Lacaze, P. C. (1991). Formation of polyparaphenylene (PPP) films by electrooxidation of biphenyl in CH2Cl2: A study of nucleation process at platinum electrode. Journal of Electroanalytical Chemistry, 303 125–137. DOI: 10.1016/0022-0728(91)85120-e.
Stejskal, J. (2013). Conducting polymer-silver composites. Chemical Papers, 67 814–848. DOI: 10.2478/s11696-012-0304-6.
Talipov, M. R., Boddeda, A., Timerghazin, Q. K., & Rathore, R. (2014). Key role of end-capping groups in optoelectronic properties of poly-p-phenylene cation radicals. The Journal of Physical Chemistry C, 118 21400–21408. DOI: 10.1021/jp5082752.
Viau, L., Hihn, J. Y., Lakard, S., Moutarlier, V., Flaud, V., & Lakard, B. (2014). Full characterization of polypyrrole thin films electrosynthesized in room temperature ionic liquids, water or acetonitrile. Electrochimica Acta, 137 298–310. DOI: 10.1016/j.electacta.2014.05.143.
Yamamoto, T., Hayashi, Y., & Yamamoto, A. (1978). A novel type of polycondensation utilizing metal-catalyzed C-C coupling. I. Preparation of thermostable polyphenylene type polymers. Bulletin of the Chemical Society of Japan, 51 2091–2097. DOI: 10.1246/bcsj.51.2091.
Yoshida, A., Mori, Y., Watanabe, M., & Naito, S. (2014). Hydrogen storage materials comprising conjugated hydrocarbon polymers with LiH: Comparison of cyclic durability between LiH-polyacetylene, -poly(p-phenylene), and -poly(diphenylacetylene) and mechanistic investigation upon LiH-poly(p-phenylene). The Journal of Physical Chemistry C, 118 19683–19687. DOI: 10.1021/jp507802b.
Zhou, W., Xu, J., Du, Y., & Yang, P. (2010). Electrochemical polymerization of p-terphenyl in mixed electrolyte of boron trifluoride diethyl etherate and CH2Cl2. Journal of Applied Polymer Science, 117 2688–2694. DOI: 10.1002/app.30927.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Eiras, C., Foschini, M., Soares, J.C. et al. Electrosynthesis of poly(p-phenylene) and poly(p-phenylene/pyrrole) films under controlled humidity. Chem. Pap. 69, 958–963 (2015). https://doi.org/10.1515/chempap-2015-0107
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1515/chempap-2015-0107