Electrosynthesis of poly(3,4-ethylenedithiathiophene) in an ionic liquid and its electrochemistry and electrochromic properties

Electrochimica Acta

Volumn 106, Issue , 2013, Pages 201-208

  Lu, Baoyang ^a,b   Zhang, Shimin ^a   Qin, Leiqiang ^a   Chen, Shuai ^c   Zhen, Shijie ^a   Xu, Jingkun ^a,b,c  

^a JIANGXI SCIENCE AND TECHNOLOGY NORMAL UNIVERSITY   (China)

^b SHANDONG UNIVERSITY   (China)

^c XINJIANG TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

Author keywords

Electrochromics; Electropolymerization; Ionic liquids; Poly(3,4 ethylenedithiathiophene); Redoping

Indexed keywords

CYCLIC VOLTAMMETRY; ELECTROCHEMISTRY; ELECTROCHROMISM; ELECTROPOLYMERIZATION; LIQUIDS; SEMICONDUCTOR DOPING; THERMOANALYSIS; ULTRAVIOLET VISIBLE SPECTROSCOPY;

1-BUTYL-3-METHYL-IMIDAZOLIUM HEXAFLUOROPHOSPHATE; COLORATION EFFICIENCIES; ELECTROCHROMIC PROPERTIES; ELECTROCHROMICS; POLY(3,4-ETHYLENEDITHIATHIOPHENE); RE-DOPING; SWITCHING VOLTAGES; UV-VIS SPECTROSCOPY;

IONIC LIQUIDS;

EID: 84879207333     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2013.05.068     Document Type: Article

References (51)

1. A. Elschner, S. Kirchmeyer, W. Lvenich, U. Merker, K. Reuter, PEDOT:. Principles and Application of an Intrinsically Conductive Polymer, Taylor & Francis Group, Boca Raton, 2011.
2. M. Turbiez, P. Frre, M. Allain, N. Gallego-Planas, J. Roncali, Effect of structural factor on the electropolymerization of bithiophenic precursors containing a 3,4-ethylenedisulfanylthiophene unit, Macromolecules 38 (2005) 6806.
3. H.J. Spencer, P.J. Skabara, M. Giles, I. McCulloch, S.J. Coles, M.B. Hursthouse, The first direct experimental comparison between the hugely contrasting properties of PEDOT and the all-sulfur analogue PEDTT by analogy with well-defined EDTT-EDOT copolymers, Journal of Materials Chemistry 15 (2005) 4783.
4. K. Zhang, B. Tieke, J.C. Forgie, F. Vilela, J.A. Parkinson, P.J. Skabara, Cross-linked polymers based on 2,3,5,6-tetra-substituted pyrrolo[3,4-c]pyrrole- 1,4(2H,5H)-dione (DPP): synthesis, optical and electronic properties, Polymer 51 (2010) 6107.
5. C.R. Mason, P.J. Skabara, D. Cupertino, J. Schofield, F. Meghdadi, B. Ebner, N.S. Sariciftci, Synthesis and properties of end-capped sexithiophenes incorporating the ethylene dithiothiophene unit, Journal of Materials Chemistry 15 (2005) 1446.
6. C.R. Mason, Y. Li, P. O'Brien, N.J. Findlay, P.J. Skabara, Sexithiophenes as efficient luminescence quenchers of quantum dots, Beilstein Journal of Organic Chemistry 7 (2011) 1722.
7. H. Pang, P.J. Skabara, D.J. Crouch, W. Duffy, M. Heeney, I. McCulloch, S.J. Coles, P.N. Horton, M.B. Hursthouse, Structural and electronic effects of 1,3,4-thiadiazole units incorporated into polythiophene chains, Macromolecules 40 (2007) 6585.
8. G.J. McEntee, P.J. Skabara, F. Vilela, S. Tierney, I.D.W. Samuel, S. Gambino, S.J. Coles, M.B. Hursthouse, R.W. Harrington, W. Clegg, Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units, Chemistry of Materials 22 (2010) 3000.
9. J. Tang, Z.P. Song, N. Shan, L.Z. Zhan, J.Y. Zhang, H. Zhan, Y.H. Zhou, C.M. Zhan, Poly[3,4-(ethylenedithio)thiophene]: high specific capacity cathode active material for lithium rechargeable batteries, Journal of Power Sources 185 (2008) 1434.
10. C.G. Wang, J.L. Schindler, C.R. Kannewurf, M.G. Kanatzidis, Poly(3,4-ethylenedithiathiophene), a new soluble conductive polythiophene derivative, Chemistry of Materials 7 (1995) 58.
11. Y. Son, K.S. Kang, C.Y. Shim, J.S. Choi, D.Y. Lee, S.Y. Hong, Preparation of conducting polymer PEDiTT thin film using SAM method, Polymer (Korea) 26 (2002) 589.
12. S.Y. Hong, Proposal of novel actuators using conducting polymer laminates, Synthetic Metals 135 (2003) 439.
13. A. Cravino, H. Neugebauer, A. Peter, P.J. Skabara, H.J. Spencer, J.J.W. McDouall, L. Dunsch, N.S. Sariciftci, Spectroelectrochemistry of poly(ethylenedithiathiophene) - the sulfur analogue of poly(ethylenedioxythiophene), Journal of Physical Chemistry B 110 (2006) 2662.
14. W. Chen, G. Xue, Low potential electrochemical syntheses of heteroaromatic conducting polymers in a novel solvent system based on trifluroborate-ethyl ether, Progress in Polymer Science 30 (2005) 783.
15. Y.H. Wijsboom, A. Patra, S.S. Zade, Y. Sheynin, M. Li, L.J.W. Shimon, M. Bendikov, Controlling rigidity and planarity in conjugated polymers: poly(3,4-ethylenedithioselenophene), Angewandte Chemie International Edition 48 (2009) 5443.
16. K. Zhang, B. Tieke, J.C. Forgie, F. Vilela, P.J. Skabara, Donor-acceptor conjugated polymers based on p- and o-benzodifuranone and thiophene derivatives: electrochemical preparation and optical and electronic properties, Macromolecules 45 (2012) 743.
17. W. Domagala, D. Palutkiewicz, D. Cortizo-Lacalle, A.L. Kanibolotsky, P.J. Skabara, Redox doping behaviour of poly(3,4-ethylenedithiothiophene) - the counterion effect, Optical Materials 33 (2011) 1405.
18. Y. Son, J. Lee, J. Kim, E. Kwon, Y. Lee, Preparation of conducting polymer/metal nanocomposites, Molecular Crystals and Liquid Crystals 444 (2006) 275.
19. R. Blanco, C. Seoane, J.L. Segura, Functionalized 3,4- ethylenedithiathiophenes (EDTTs) as building blocks for poly (3,4-ethylenedithiathiophene) (PEDTT) derivatives, Tetrahedron Letters 49 (2008) 2056.
20. C. Pozo-Gonzalo, T. Khan, J.J.W. McDouall, P.J. Skabara, D.M. Roberts, M.E. Light, S.J. Coles, M.B. Hursthouse, H. Neugebauer, A. Cravinod, N.S. Sariciftci, Synthesis and electropolymerisation of 3′,4′- bis(alkylsulfanyl)terthiophenes and the significance of the fused dithiin ring in 2,5-dithienyl-3,4-ethylenedithiothiophene (DT-EDTT), Journal of Materials Chemistry 12 (2002) 500.
21. B. Dong, J.K. Xu, L.Q. Zheng, Ionic liquids for the electrosyntheses of conducting polymers, Progress in Chemistry 21 (2009) 1792.
22. K. Sekiguchi, M. Atobe, T. Fuchigami, Electrooxidative polymerization of aromatic compounds in 1-ethyl-3-methylimidazolium trifluoromethanesulfonate room-temperature ionic liquid, Journal of Electroanalytical Chemistry 557 (2003) 1.
23. J.M. Pringle, J. Efthimiadis, P.C. Howlett, J. Efthimiadis, D.R. MacFarlane, A.B. Chaplin, S.B. Hall, D.L. Officer, G.G. Wallace, M. Forsyth, Electrochemical synthesis of polypyrrole in ionic liquids, Polymer 45 (2004) 1447.
24. J.M. Pringle, M. Forsyth, D.R. MacFarlane, K. Wagner, S.B. Hall, D.L. Officer, The influence of the monomer and the ionic liquid on the electrochemical preparation of polythiophene, Polymer 46 (2005) 2047.
25. Y.H. Pang, X.Y. Li, H.L. Ding, G.Y. Shi, L.T. Jin, Electropolymerization of high quality electrochromic poly(3-alkyl-thiophene)s via a room temperature ionic liquid, Electrochimica Acta 52 (2007) 6172.
26. C. Arbizzani, F. Soavi, M. Mastragostino, A novel galvanostatic polymerization for high specific capacitance poly(3-methylthiophene) in ionic liquid, Journal of Power Sources 162 (2006) 735.
27. E. Naudin, H.A. Ho, S. Branchaud, L. Breau, D. Béanger, Electrochemical polymerization and characterization of poly(3-(4-fluorophenyl) thiophene) in pure ionic liquids, Journal of Physical Chemistry B 106 (2002) 10585.
28. P. Damlin, C. Kvarnstrm, A. Ivaska, Electrochemical synthesis and in situ spectroelectrochemical characterization of poly(3,4-ethylenedioxythiophene) (PEDOT) in room temperature ionic liquids, Journal of Electroanalytical Chemistry 570 (2004) 113.
29. H. Randriamahazaka, C. Plesse, D. Teyssié, C. Chevrot, Ions transfer mechanisms during the electrochemical oxidation of poly(3,4- ethylenedioxythiophene) in 1-ethyl-3-methylimidazolium bis((trifluoromethyl) sulfonyl)amide ionic liquid, Electrochemistry Communications 6 (2004) 299.
30. D. Wei, C. Kvarnström, T. Lindfors, A. Ivaska, Electrochemical functionalization of single walled carbon nanotubes with polyaniline in ionic liquids, Electrochemistry Communications 9 (2007) 206.
31. M.C. Li, C.A. Ma, B.Y. Liu, Z.M. Jin, A novel electrolyte 1-ethylimidazolium trifluoroacetate used for electropolymerization of aniline, Electrochemistry Communications 7 (2005) 209.
32. O. Schneider, A. Bund, A. Ispas, N. Borissenko, S. Zein El Abedin, F. Endres, An EQCM study of the electropolymerization of benzene in an ionic liquid and ion exchange characteristics of the resulting polymer film, Journal of Physical Chemistry B 109 (2005) 7159.
33. B. Dong, L.Q. Zheng, J.K. Xu, H.T. Liu, S.Z. Pu, Electropolymerization of 1,2-methylenedioxybenzene in 1-butyl-3-methylimidazolium hexafluorophosphate room temperature ionic liquid, Polymer 48 (2007) 5548.
34. B. Dong, Y.H. Xing, J.K. Xu, L.Q. Zheng, J. Hou, F. Zhao, Electrosyntheses of free-standing and highly conducting polyselenophene films in an ionic liquid, Electrochimica Acta 53 (2008) 5745.
35. B. Dong, S.H. Zhang, L.Q. Zheng, J.K. Xu, Ionic liquid microemulsions: a new medium for electropolymerization, Journal of Electroanalytical Chemistry 619-620 (2008) 193.
36. B. Dong, J.K. Xu, L.Q. Zheng, J. Hou, Electrodeposition of conductive poly(3-methoxythiophene) in ionic liquid microemulsions, Journal of Electroanalytical Chemistry 628 (2009) 60.
37. B. Dong, D.F. Song, L.Q. Zheng, J.K. Xu, N. Li, Electrosynthesis of polyfluorene in an ionic liquid and characterization of its stable electrocatalytic activity for formic acid oxidation, Journal of Electroanalytical Chemistry 633 (2009) 63.
38. S. Chen, B.Y. Lu, X.M. Duan, J.K. Xu, Systematic study on chemical oxidative and solid-state polymerization of poly(3,4-ethylenedithiathiophene), Journal of Polymer Science Part A: Polymer Chemistry 50 (2012) 1967.
39. J. Dupont, C.S. Consorti, P.A.Z. Suarez, R.F. de Souza, S.L. Fulmer, D.P. Richardson, T.E. Smith, S. Wolff, Preparation of 1-butyl-3-methyl imidazolium-based room temperature ionic liquids, Organic Syntheses 79 (2002) 236.
40. C.L. Gaupp, D.M. Welsh, R.D. Rauh, J.R. Reynolds, Composite coloration efficiency measurements of electrochromic polymers based on 3,4- alkylenedioxythiophenes, Chemistry of Materials 14 (2002) 3964.
41. B.D. Reeves, C.R.G. Grenier, A.A. Argun, A. Cirpan, T.D. McCarley, J.R. Reynolds, Spray coatable electrochromic dioxythiophene polymers with high coloration efficiencies, Macromolecules 37 (2004) 7559.
42. J. Roncali, Conjugated poly(thiophenes): synthesis, functionalization, and applications, Chemical Reviews 92 (1992) 711.
43. A.J. Downard, D. Pletcher, A study of the conditions for the electrodeposition of polythiophene in acetonitrile, Journal of Electroanalytical Chemistry 206 (1986) 147.
44. M. Zhou, J. Heinze, Electropolymerization of pyrrole and electrochemical study of polypyrrole: 1. Evidence for structural diversity of polypyrrole, Electrochimica Acta 44 (1999) 1733.
45. G.Q. Shi, J.K. Xu, M.X. Fu, Raman spectroscopic and electrochemical studies on the doping level changes of polythiophene films during their electrochemical growth processes, Journal of Physical Chemistry B 106 (2002) 288-292.
46. M.X.G. Fu, Q. Shi, F.E. Chen, X.Y. Hong, Doping level change of polythiophene film during its electrochemical growth process, Physical Chemistry Chemical Physics 4 (2002) 2685.
47. G. Inzelt, M. Pineri, J.W. Schultze, M.A. Vorotyntsev, Electron and proton conducting polymers: recent developments and prospects, Electrochimica Acta 45 (2000) 2403.
48. M.A. Vorotyntsev, J.P. Badiali, Short-range electron-ion interaction effects in charging the electroactive polymer films, Electrochimica Acta 39 (1994) 289.
49. F. Uckert, Y.H. Tak, K. Müllen, H. Bässler, 2,7-Poly(9-fluorenone): a trap-free electron-injection material with a high charge carrier mobility for use in lightemitting diodes, Advanced Materials 12 (2000) 905.
50. S.D.D.V. Rughooputh, S. Hotta, A.J. Heeger, F. Wudl, Chromism of soluble polythienylenes, Journal of Polymer Science Part B: Polymer Physics 25 (1987) 1071.
51. P.M. Beaujuge, J.R. Reynolds, Color control in π-conjugated organic polymers for use in electrochromic, Chemical Reviews 110 (2010) 268.