Low-potential electrosynthesis of a novel nitrogen analog of PEDOT in an ionic liquid and its optoelectronic properties

Electrochimica Acta

Volumn 160, Issue , 2015, Pages 160-168

  Feng, Zilan ^a   Mo, Daize ^a   Wang, Zhipeng ^a   Zhen, Shijie ^a   Xu, Jingkun ^a   Lu, Baoyang ^a   Ming, Shouli ^a   Lin, Kaiwen ^a   Xiong, Jinhua ^a  

^a JIANGXI SCIENCE AND TECHNOLOGY NORMAL UNIVERSITY   (China)

Author keywords

Electrochromics; Electropolymerization; Ionic liquid; PEDOT analog; Spectroelectrochemistry

Indexed keywords

CYCLIC VOLTAMMETRY; ELECTROPOLYMERIZATION; ENERGY GAP; IONIC LIQUIDS; NITROGEN; SEMICONDUCTOR DOPING; SPECTROELECTROCHEMISTRY;

1-BUTYL-3-METHYL-IMIDAZOLIUM HEXAFLUOROPHOSPHATE; 3 ,4 ETHYLENEDIOXYTHIOPHENE (EDOT); ELECTROCHEMICAL STABILITIES; ELECTROCHEMICAL STUDIES; ELECTROCHROMICS; OPTOELECTRONIC PROPERTIES; OXIDATION POTENTIALS; PEDOT ANALOG;

LIQUIDS;

EID: 84922867374     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2015.02.054     Document Type: Article

References (50)

1. A. Elschner, S. Kirchmeyer, W. Lovenich, U. Merker, and K. Reuter PEDOT: Principles and applications of an intrinsically conductive polymer 2011 CRC Press
2. L. Groenendaal, F. Jonas, D. Freitag, H. Pielartzik, and J.R. Reynolds Poly(3,4-ethylenedioxythiophene) and its derivatives: Past, present, and future Advanced Materials 12 2000 481 494
3. L. Groenendaal, G. Zotti, P.H. Aubert, S.M. Waybright, and J.R. Reynolds Electrochemistry of poly(3,4-alkylenedioxythiophene) derivatives Advanced Materials 15 2003 855 879
4. T.A. Skotheim, and J. Reynolds Conjugated polymers: processing and applications 2006 CRC press
5. G. Heywang, and F. Jonas Poly(alkylenedioxythiophene) s-New very stable conducting polymers Advanced Materials 4 1992 116 118
6. S.C. Ng, H.S.O. CHAN, and W.L. Yu Synthesis and characterization of electrically conducting copolymers of ethylenedioxythiophene and 1,3-propylenedioxythiophene with ω-functional substituents Journal of Materials Science Letters 16 1997 809 811
7. A. Kumar, D.M. Welsh, M.C. Morvant, F. Piroux, K.A. Abboud, and J.R. Reynolds Conducting poly(3,4-alkylenedioxythiophene) derivatives as fast electrochromics with high-contrast ratios Chemistry of Materials 10 1998 896 902
8. Z.C. Xu, J.H. Kang, F. Wang, S.M. Paek, S.J. Hwang, Y. Kim, S.J. Kim, J.H. Choy, and J. Yoon Synthesis of large ring 3,4-alkylenedioxythiophenes (ADOT) derivatives via Mitsunobu reaction Tetrahedron Letters 52 2011 2823 2825
9. C. Alemán, E. Armelin, J.I. Iribarren, F. Liesa, M. Laso, and J. Casanovas Structural and electronic properties of 3,4-ethylenedioxythiophene, 3,4-ethylenedisulfanylfurane and thiophene oligomers: A theoretical investigation Synthetic Metals 149 2005 151 156
10. H. Pang, P.J. Skabara, S. Gordeyev, J.J.W. McDouall, S.J. Coles, and M.B. Hursthouse Poly(3,4-ethylenediselena) thiophene-The selenium equivalent of PEDOT Chemistry of Materials 19 2006 301 307
11. Y.H. Wijsboom, Y. Sheynin, A. Patra, N. Zamoshchik, R. Vardimon, G. Leitus, and M. Bendikov Tuning of electronic properties and rigidity in PEDOT analogs Journal of Materials Chemistry 21 2011 1368 1372
12. H.C. Li, C. Lambert, and R. Stahl Conducting polymers based on alkylthiopyrroles Macromolecules 39 2006 2049 2055
13. S. Chen, B.Y. Lu, X.M. Duan, and 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 1978
14. M. Turbiez, P. Frère, M. Allain, N. Gallego-Planas, and J. Roncali Effect of structural factor on the electropolymerization of bithiophenic precursors containing a 3,4-ethylenedisulfanylthiophene unit Macromolecules 38 2005 6806 6812
15. P. Blanchard, A. Cappon, E. Levillain, Y. Nicolas, P. Frère, and J. Roncali Thieno[3,4-b]-1,4-oxathiane:è An unsymmetrical sulfur analogue of 3,4-ethylenedioxythiophene (EDOT) as a building block for linear π-conjugated systems Organic Letters 4 2002 607 609
16. S. Inagi, and T. Fuchigami Electronic property and reactivity of novel fused thiophene Synthetic Metals 158 2008 782 784
17. H.C. Li, and C. Lambert 3,4-Methylenedithiopyrrole: Convenient synthesis and application as a novel monomer for electroactive polymers Carbon 15 2005 1235 1237
18. G. Zotti, S. Zecchin, G. Schiavon, and L.B. Groenendaal Conductive and magnetic properties of 3,4-dimethoxy-and 3,4-ethylenedioxy-capped polypyrrole and polythiophene Chemistry of Materials 12 2000 2996 3005
19. P. Schottland, K. Zong, C.L. Gaupp, B.C. Thompson, C.A. Thomas, I. Giurgiu, R. Hickman, K.A. Abboud, and J.R. Reynolds Poly(3,4-alkylenedioxypyrrole) s: Highly stable electronically conducting and electrochromic polymers Macromolecules 33 2000 7051 7061
20. C.A. Thomas, K. Zong, P. Schottland, and J.R. Reynolds Poly(3,4-alkylenedioxypyrrole) s as highly stable aqueous-compatible conducting polymers with biomedical implications Advanced Materials 12 2000 222 225
21. E. Ermiş, D. Yiʇit, and M. Güllü Synthesis of poly(N-alkyl-3,4-dihydrothieno[3,4-b][1,4]oxazine) derivatives and investigation of their supercapacitive performances for charge storage applications Electrochimica Acta 90 2013 623 633
22. A.P. Abbott, and K.J. McKenzie Application of ionic liquids to the electrodeposition of metals Physical Chemistry Chemical Physics 8 2006 4265 4279
23. D.R. MacFarlane, J.M. Pringle, P.C. Howlett, and M. Forsyth Ionic liquids and reactions at the electrochemical interface Physical Chemistry Chemical Physics 12 2010 1659 1669
24. F. Endres, D. MacFarlane, and A. Abbott Electrodeposition from ionic liquids 2008 John Wiley & Sons
25. K. Sekiguchi, M. Atobe, and T. Fuchigami Electrooxidative polymerization of aromatic compounds in 1-ethyl-3-methylimidazolium trifluoromethanesulfonate room-temperature ionic liquid Journal of Electroanalytical Chemistry 557 2003 1 7
26. 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, and M. Forsyth Electrochemical synthesis of polypyrrole in ionic liquids Polymer 45 2004 1447 1453
27. D. Wei, C. Kvarnstrom, T. Lindfors, and A. Ivaska Electrochemical functionalization of single walled carbon nanotubes with polyaniline in ionic liquids Electrochemistry Communications 9 2007 206 210
28. M.C. Li, C.A. Ma, B.Y. Liu, and Z.M. Jin A novel electrolyte 1-ethylimidazolium trifluoroacetate used for electropolymerization of aniline Electrochemistry Communications 7 2005 209 212
29. B. Dong, D.F. Song, L.Q. Zheng, J.K. Xu, and 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 70
30. P. Damlin, C. Kvarnström, and 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 113 122
31. H. Randriamahazaka, C. Plesse, D. Teyssié, and 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 299 305
32. B. Dong, S.H. Zhang, L.Q. Zheng, and J.K. Xu Ionic liquid microemulsions: A new medium for electropolymerization Journal of Electroanalytical Chemistry 619-620 2008 193 196
33. X.M. Qi Preparation in ionic liquids, properties and applications of conducting polymers [D] 2005 East China Normal Universiy Shanghai, China
34. B.Y. Lu, S.M. Zhang, L.Q. Qin, S. Chen, S.J. Zhen, and J.K. Xu Electrosynthesis of poly(3,4-ethylenedithiathiophene) in an ionic liquid and its electrochemistry and electrochromic properties Electrochimica Acta 106 2013 201 208
35. Z.P. Wang, J.K. Xu, B.Y. Lu, S.M. Zhang, L.Q. Qin, D.Z. Mo, and S.J. Zhen Poly(thieno[3,4-b]-1,4-oxathiane): Medium effect on electropolymerization and electrochromic performance Langmuir 30 2014 15581 15589
36. B.D. Reeves, C.R.G. Grenier, A.A. Argun, A. Cirpan, T.D. McCarley, and J.R. Reynolds Spray coatable electrochromic dioxythiophene polymers with high coloration efficiencies Macromolecules 37 2004 7559 7569
37. C.L. Gaupp, D.M. Welsh, R.D. Rauh, and J.R. Reynolds Composite coloration efficiency measurements of electrochromic polymers based on 3,4-alkylenedioxythiophenes Chemistry of Materials 14 2002 3964 3970
38. M. Zhou, and J. Heinze Electropolymerization of pyrrole and electrochemical study of polypyrrole. 3. Nature of water effect in acetonitrile The Journal of Physical Chemistry B 103 1999 8451 8457
39. C. Li, and T. Imae Electrochemical and optical properties of the poly(3,4-ethylenedioxythiophene) film electropolymerized in an aqueous sodium dodecyl sulfate and lithium tetrafluoroborate medium Macromolecules 37 2004 2411 2416
40. N. Sakmeche, S. Aeiyach, J.J. Aaron, M. Jouini, J.C. Lacroix, and P.C. Lacaze Improvement of the electrosynthesis and physicochemical properties of poly(3,4-ethylenedioxythiophene) using a sodium dodecyl sulfate micellar aqueous medium Langmuir 15 1999 2566 2574
41. B. Dong, J.K. Xu, L.Q. Zheng, and J. Hou Electrodeposition of conductive poly(3-methoxythiophene) in ionic liquid microemulsions Journal of Electroanalytical Chemistry 628 2009 60 66
42. S. Beyazyildirim, P. Camurlu, D. Yilmaz, M. Gullu, and L. Toppare Synthesis and electrochromic properties of conducting copolymers of dioxocino- and dithiocino-quinoxalines with bithiophene Journal of Electroanalytical Chemistry 587 2006 235 246
43. C. Wang, J.L. Schindler, C.R. Kannewurf, and M.G. Kanatzidis Poly(3,4-ethylenedithiathiophene). A new soluble conductive polythiophene derivative Chemistry of Materials 7 1995 58 68
44. W. Chen, and 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 783 811
45. B. Dong, L.Q. Zheng, J.K. Xu, H.T. Liu, and S.Z. Pu Electropolymerization of 1,2-methylenedioxybenzene in 1-butyl-3-methylimidazolium hexafluorophosphate room temperature ionic liquid Polymer 48 2007 5548 5555
46. M.X. Fu, G.Q. Shi, F.G. Chen, and X.Y. Hong Doping level change of polythiophene film during its electrochemical growth process Physical Chemistry Chemical Physics 4 2002 2685 2690
47. H. Goto, and K. Akagi Optically active electrochromism of poly(3,4-ethylenedioxythiophene) synthesized by electrochemical polymerization in lyotropic liquid crystal of hydroxypropyl cellulose/water: Active control of optical activity Chemistry of Materials 18 2006 255 262
48. H.J. Spencer, P.J. Skabara, M. Giles, I. McCulloch, S.J. Coles, and 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
49. W. Domagala, D. Palutkiewicz, D. Cortizo-Lacalle, A.L. Kanibolotsky, and P.J. Skabara Redox doping behaviour of poly(3,4-ethylenedithiothiophene)-The counterion effect Optical Materials 33 2011 1405 1409
50. C. Zhang, Y. Xu, N.C. Wang, Y. Xu, W.Q. Xiang, O.Y. Mi, and C.N. Ma Electrosyntheses and characterizations of novel electrochromic copolymers based on pyrene and 3,4-ethylenedioxythiophene Electrochimica Acta 55 2009 13 18