Low potential electrosyntheses of free-standing polyfluorene films in boron trifluoride diethyl etherate

European Polymer Journal

Volumn 42, Issue 5, 2006, Pages 1154-1163

  Xu, Jingkun ^a   Zhang, Yajuan ^a,b   Hou, Jian ^a   Wei, Zhenhong ^a,c   Pu, Shouzhi ^a   Zhao, Jiquan ^b   Du, Yukou ^c  

^a Nanchang Normal University   (China)

^b HEBEI UNIVERSITY OF TECHNOLOGY   (China)

^c SOOCHOW UNIVERSITY   (China)

Author keywords

Boron trifluoride diethyl etherate; Electrochemical polymerization; Inherently conducting polymers; Polyfluorene

Indexed keywords

ACETONITRILE; ELECTROCHEMISTRY; POLYMERIZATION; STAINLESS STEEL; SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY;

BORON TRIFLUORIDE DIETHYL ETHERATE; INHERENTLY CONDUCTING POLYMERS; POLYFLUORENE;

PLASTIC FILMS;

EID: 33645976892     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2005.10.014     Document Type: Article

References (63)

1. Leclerc M. Polyfluorenes: twenty years of progress. J Polym Sci Part A: Polym Chem 39 (2001) 2867-2873
2. Scherf U., and List E.J.W. Semiconducting polyfluorenes-towards reliable structure-property relationships. Adv Mater 14 7 (2002) 477-487
3. Hou Q., Zhou Q.M., Zhang Y., Yang W., Yang R.Q., and Cao Y. Synthesis and electroluminescent properties of high-efficiency saturated red emitter based on copolymers from fluorene and 4,7-di(4-hexylthien-2-yl)-2,1,3-benzothiadiazole. Macromolecules 37 17 (2004) 6299-6305
4. Fu Y.Q., Li Y., Li J., Yan S., and Bo Z.S. High molecular weight dendronized poly(fluorene)s with peripheral carbazole groups: Synthesis, characterization, and properties. Macromolecules 37 17 (2004) 6395-6400
5. Fang Q., and Yamamoto T. New alternative copolymer constituted of fluorene and triphenylamine units with a tunable -CHO group in the side chain. Quantitative transformation of the -CHO group to -CH{double bond, long}CHAr groups and optical and electrochemical properties of the polymers. Macromolecules 37 16 (2004) 5894-5899
6. Liu X.M., He C.B., Hao X.T., Tan L.W., Li Y.Q., and Ong K.S. Hyperbranched blue-light-emitting alternating copolymers of tetrabromoarylmethane/silane and 9,9-dihexylfluorene-2,7-diboronic acid. Macromolecules 37 16 (2004) 5965-5970
7. Banach M.J., Friend R.H., and Sirringhaus H. Influence of the casting solvent on the thermotropic alignment of thin liquid crystalline polyfluorene copolymer films. Macromolecules 37 16 (2004) 6079-6085
8. Wu L.B., Sato T., Tang H.Z., and Fujiki M. Conformation of a polyfluorene derivative in solution. Macromolecules 37 16 (2004) 6183-6188
9. Cho N.S., Hwang D.H., Jung B.J., Lim E., Lee J., and Shim H.K. Synthesis, characterization, and electroluminescence of new conjugated polyfluorene derivatives containing various dyes as comonomers. Macromolecules 37 14 (2004) 5265-5273
10. Asawapirom U., Bulut F., Farrell T., Gadermaier C., Gamerith S., Guntner R., et al. Materials for polymer electronics applications semiconducting polymer thin films and nanoparticles. Macromol Symp 212 (2004) 83-91
11. Martin S.J., Kambili A., and Walker A.B. Effect of spatial irregularities on the temperature and field dependence of the mobility in liquid-crystalline conjugated polymer films. Macromol Symp 212 (2004) 263-268
12. Morgado J., Charas A., Barbagallo N., Alcacer L., Matos M., and Cacialli F. Effect of a dipolar self-assembly monolayer formation on indium-tin oxide on the performance of single-layer polymer-based light-emitting diodes. Macromol Symp 212 (2004) 381-386
13. Imamoglu T., and Onal A.M. Electrochemical polymerization of 2-aminofluorene in ethylalcohol/water medium. Eur Polym J 40 8 (2004) 1875-1880
14. Rault-Berthelot J., Raoult E., Tahri-Hassani J., Le Deit H., and Simonet J. Anodic polymerization of N-(9-fluorenylmethoxycarbonyl) amino acids towards chiral conducting polymers. Electrochim Acta 44 19 (1999) 3409-3419
15. Klaerner G., and Miller R.D. Polyfluorene derivatives: Effective conjugation lengths from well-defined oligomers. Macromolecules 31 6 (1998) 2007-2009
16. Higgins S.J., Jones C.L., and Francs S.M. Synthesis and electropolymerization of 1,1′-bis(5-oligothienyl) ferrocenes: poly (oligothiophene-ferrocene) modified electrodes. Synth Met 97 3 (1998) 211-215
17. Raultberthelot J., Massaoudi M., Ledeit H., and Simonet J. Anodic polymerization of difluorenyls linked with polyether or alkyl spacers: Synthesis of polyfluorenes with potential complexing properties. Synth Met 75 1 (1995) 11-23
18. Raultberthelot J., Massaoudi M., and Roze C. Anodic-oxidation of the 1-(pyrrol-1-yl)-5-(fluoren-9-yl)-3-oxapentane synthesis of a conducting poly (pyrrole-fluorene). J Electroanal Chem 388 1-2 (1995) 187-193
19. Simonet J., Raultberthelot J., Granger M.M., and Ledeit H. Cathodic cleavage of organic-compounds on electrodes coated with polymeric materials-catalytic efficiency of solid cathodes modified by polyfluorenes or polydibenzofuran. J Electroanal Chem 372 (1994) 185-193
20. Raultberthelot J., Angely L., Delaunay J., and Simonet J. The polyfluorenes-a family of versatile electroactive polymers. 2. Poly (9,9-disubstituted fluorenes) existence of reversible para-doping or normal-doping. New J Chem 11 6 (1987) 487-494
21. 4: Electrochemical behavior of the derived oxidation products. J Solid State Electrochem 3 5 (1999) 292-298
22. Raultberthelot J., Roze C., and Granger M.M. Anodic oxidation of 2(9H-fluoren-9-ylidene) malononitrile and 2(9H-fluoren-9-ylidene)-2-phenylacetonitrile. Electrochemical behavior and physicochemical properties of the derived polymers. J Electroanal Chem 436 1-2 (1997) 85-101
23. Novak P., Muller K., Santhanam K.S.V., and Haas O. Electrochemically active polymers for rechargeable batteries. Chem Rev 97 1 (1997) 207-281
24. Raultberthelot J., and Granger M.M. Bi- and trilayer electrodes employing polyfluorenes and polydibenzofuran. A cyclic voltammetry investigation. Synth Met 82 2 (1996) 103-109
25. Raultberthelot J., Cariou M., and Tahrihassani J. Anodic oxidation of 9,9-dimethyl-2-phenylfluorene: Towards sequential poly (fluorine-phenylene)-Comparison with polymers obtained in mixtures of oligophenylene and 9,9-dimethylfluorene. J Electroanal Chem 402 1-2 (1996) 203-210
26. Raultberthelot J., Massaoud M.I., Ledeit H., and Simonet J. Anodic polymerization of difluorenyls linked with polyether or alkyl spacers: Synthesis of polyfluorenes with potential complexing properties. Synth Met 75 1 (1995) 11-23
27. Knaapila M., Lyons B.P., Hase T.P.A., Pearson C., Petty M.C., Bouchenoire L., et al. Influence of molecular weight on the surface morphology of aligned, branched side-chain polyfluorene. Adv Funct Mater 15 9 (2005) 1517-1522
28. Raultberthelot J., Granger M., Simonet J., Ledeit H., Lemennquestaigne V., Massaoudi M., et al. Polyfluorenes-assessment and future perspectives. J Chem Phys PCB 92 4 (1995) 867-870
29. Raultberthelot J., and Granger M.M. Cathodic polymerization of acrylonitrile at polyfluorene-modified electrodes in aprotic media. J Electroanal Chem 382 1-2 (1995) 169-174
30. Raultberthelot J., Ledeit H., Massaoudi M., and Simonet J. Anodic-oxidation of 9,9′-bifluorenylidene-electrochemical behavior and physicochemical properties of relevant polymers. J Electroanal Chem 380 1-2 (1995) 237-247
31. Su H.J., Wu F.I., Tseng Y.H., and Shu C.F. Color tuning of a light-emitting polymer: Polyfluorene-containing pendant amino-substituted distyrylarylene units. Adv Funct Mater 15 7 (2005) 1209-1216
32. Ledeit H., Raultberthelot J., and Simonet J. Anodic oxidation of bis(9,9-beta-cyanoethyl) fluorene an efficient way for synthesizing a new functionalizable conducting polymer. Synth Met 47 3 (1992) 373-376
33. Raultberthelot J., Questaigne V., Simonet J., and Peslerbe G. A new device for the in situ UV-Visible spectroelectrochemical study of polymeric films set on solid-surfaces application to the study of the electrochemical-behavior of polyfluorenes. New J Chem 13 1 (1989) 45-52
34. Simonet J., and Raultberthelot J. Electrochemistry-a technique to form, to modify and to characterize organic conducting polymers. Prog Solid State 21 1 (1991) 1-48
35. Raultberthelot J., Orliac M.A., and Simonet J. The polyfluorenes-a family of versatile electroactive polymers 3. Poly(9,9-dimethylfluorene) as an electrode modifier in the study of some systems known to be reversible on platinum. Electrochim Acta 33 6 (1988) 811-823
36. Raultberthelot J., Abon G., and Simonet J. Catalytic behavior of polymeric coatings in cathodic cleavage reactions-The importance of using polyfluorene. J Electroanal Chem 240 1-2 (1988) 355-359
37. Cihaner A., Tirkes S., and Onal A.M. Electrochemical polymerization of 9-fluorenone. J Electroanal Chem 568 (2004) 151-156
38. Oudard J.F., Allendoerfer R.D., and Osteryoung R.A. Simultaneous EPR electrochemical measurements on polyfluorene in ambient temperature ionic liquids. Synth Met 22 4 (1988) 407-414
39. Janiszewska L., and Osteryoung R.A. Formation and electrochemistry of polyfluorene in ambient temperature ionic liquids. J Electrochem Soc 135 (1988) 116-122
40. Gilberto S., and Gianni Z. Anodic and cathodic deposition of electroactive polyfluorene films. J Electroanal Chem 186 (1985) 191-199
41. Groenendaal L.B., Jonas F., Freitag D., Pielartzik H., and Reynolds J.R. Poly (3,4-ethylenedioxythiophene) and its derivatives: past, present, and future. Adv Mater 12 7 (2000) 481-494
42. Groenendaal L.B., Gianni Z., Aubert P.H., Waybright S.M., and Reynolds J.R. Electrochemistry of poly (3,4-allylenedioxythiophene)derivatives. Adv Mater 15 11 (2003) 855-879
43. Shi G., Jin S., Xue G., and Li C. A conducting polymer film stronger than aluminum. Science 267 (1995) 994-996
44. Xu J.K., Nie G.M., Zhang S.S., Han X.J., Pu S.Z., Shen L., et al. Electrosyntheses of poly (2,3-benzofuran) films in boron trifluoride diethyl etherate containing poly (ethylene glycol) oligomers. Eur Polym J 41 7 (2005) 1654-1661
45. Xu J.K., Shi G.Q., Xu Z.J., Chen F., and Hong X.Y. Low potential electrochemical polymerization of 3-chlorothiophene in mixed electrolytes of boron trifluoride diethyl etherate and trifluoroacetic acid. J Electroanal Chem 514 (2001) 16-25
46. Shi G.Q., Li C., and Liang Y.Q. High-strength conducting polymers prepared by electrochemical polymerization in BFEE. Adv Mater 11 (1999) 1145-1146
47. Li C., Shi G., Liang Y., Ye W., and Sha Z.L. High-quality poly (p-phenylene)film prepared by electrochemical polymerization of benzene at a stainless steel electrode. Polymer 38 (1997) 5023-5026
48. Li C., Shi G.Q., and Liang Y.Q. Elecrochemical synthesis of free-standing poly (p-phenylene) films trifluoride diethyl etherate and sulfuric acid. Synth Met 104 (1999) 113-117
49. Wang F., Shi G.Q., Chen F., Xu J.K., and Zhang J.X. Electrochemical polymerization of thianaphthene. J Electroanal Chem 510 (2001) 29-34
50. Xu J.K., Shi G.Q., Zhang J.X., and Hong X.Y. Electrochemical polymerization of thianaphthene in mixed electrolytes of boron trifluoride diethyl etherate and trifluoroacetic acid. Macromol Chem Phys 203 (2002) 2385-2390
51. Huang Z.M., Qu L.T., Shi G.Q., Chen F., and Hong X.Y. Electrochemical polymerization of naphthalene in the electrolyte of boron trifluoride diethyl etherate containing trifluoroacetic acid and polyethylene glycol oligomer. J Electroanal Chem 55 (2003) 159-165
52. Shi G.Q., Xue G., Li C., and Lin S. Layed poly (naphthalene) films prepared by electrochemical polymerization. Polym Bull 33 (1994) 325-329
53. Huang Z.M., Shi G.Q., Qu L.T., and Hong X.Y. Electrochemical polymerization of β-naphthalene sulfonic acid in the mixed electrolyte of boron trifluoride diethyl etherate and trifluoroacetic acid. J Electroanal Chem 544 (2003) 41-46
54. Xu J.K., Nie G.M., Zhang S.S., Han X.J., Hou J., and Pu S.Z. Electrosyntheses of free-standing polyindole films in boron trifluoride diethyl etherate. J Polym Sci Part A: Polym Chem 43 17 (2005) 1444-1453
55. Xu J.K., Zhou W.Q., Hou J., Pu S.Z., Yan L.H., and Wang J.W. Electrosyntheses of high-quality poly (5-nitroindole) films in boron trifluoride diethyl etherate containing additional diethyl ether. J Polym Sci Part A: Polym Chem 43 17 (2005) 3986-3997
56. Xu J.K., Zhou W.Q., Hou J., Pu S.Z., Yan L.H., and Wang J.W. Electrosyntheses of high quality poly (5-nitroindole) films. Mater Lett 59 19-20 (2005) 2412-2417
57. Xu J.K., Hou J., Zhang S.S., Nie G.M., Pu S.Z., Shen L., et al. Electrosyntheses of high quality freestanding polyselenophene films in boron trilfuoride diethyl etherate. J Electroanal Chem 578 2 (2005) 345-355
58. Pu S.Z., Hou J., Xu J.K., Nie G.M., Zhang S.S., and Shen L. Electrosyntheses of freestanding and conducting polyselenophene films. Mater Lett 59 8-9 (2005) 1061-1065
59. Li C., Chen F., Shi G.Q., Xu J.K., and Xu Z.J. Electrosynthesis of free-standing poly (p-phenylene) films in mixed electrolytes of boron trifluoride diethyl etherate and trifluoroacetic acid on stainless steel electrode. J Appl Polym Sci 83 (2002) 2462-2666
60. Zhou M., and Heinze J. Electropolymerization of pyrrole and electrochemical study of pyrrole: 1. Evidence for structural diversity of polypyrrole. Electrochim Acta 44 (1999) 1733-1748
61. Chen X., and Inganas O. Three-step redox in polythiophenes: evidence from electrochemistry at an ultramicroelectrode. J Phys Chem 100 37 (1996) 15202-15206
62. Rong GB, Zhu SZ. Structure determination of organic compounds table of spectral data. Shanghai: East China University of Science and Technology, 2002. p. 96-103.
63. Thieblemont J.C., Brun A., Marty J., Planche M.F., and Calo P. Thermal analysis of polypyrrole oxidation in air. Polymer 36 8 (1995) 1605-1610