Electrochemical synthesis of polymers with alternate phenothiazine and bithiophene units

Electrochimica Acta

Volumn 53, Issue 5, 2008, Pages 2545-2552

  Łapkowski, Mieczysław ^a,b   Plewa, Sylwia ^a   Stolarczyk, Agnieszka ^a   Doskocz, Jacek ^c   Sołoducho, Jadwiga ^c   Cabaj, Joanna ^c   Bartoszek, Mariola ^d   Sułkowski, Wiesław W ^d  

^a SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

^b CENTRE OF POLYMER AND CARBON MATERIALS   (Poland)

^c WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^d UNIVERSITY OF SILESIA   (Poland)

Author keywords

Cyclic voltammetry; ESR; Oxidation mechanism; Phenothiazine derivatives; Radical cation

Indexed keywords

CYCLIC VOLTAMMETRY; ELECTROPOLYMERIZATION; MONOMERS; OXIDATION; SPECTROELECTROCHEMISTRY; SYNTHESIS (CHEMICAL);

PHENOTHIAZINE DERIVATIVES; RADICAL CATION;

POLYMERS;

EID: 37349123945     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2007.10.031     Document Type: Article

References (60)

1. Yu G., and Heeger A.J. J. Appl. Phys. 78 (1995) 4510-4515
2. Halls J.J.M., Walsh C.A., Greenham N.C., Marseglia E.A., Friend R.H., Moratti S.C., and Holmes A.B. Nature (London) 376 (1995) 498-500
3. Bao Z., Dodabalapur A., and Lovinger A. Appl. Phys. Lett. 69 (1996) 4108-4110
4. Jenekhe S.A., Zhang X., Chen X.L., Choong V.-E., Gao Y., and Hsieh B.R. Chem. Mater. 9 (1997) 409-412
5. Sirringhaus H., Tessler N., and Friend R.H. Science 20 (1998) 1741-1744
6. Kraft A., Grimsdale A.C., and Holmes A.B. Angew. Chem., Int. Ed. 37 (1998) 402-428
7. Friend R.H., Gymer R.W., Holmes A.B., Burroughes J.H., Marks R.N., Taliani C., Bradley D.D.C., Dos Santos D.A., Bredas J.L., Logdlund M., and Salaneck W.R. Nature (London) 397 (1999) 121-128
8. Heeger A.J. Angew. Chem., Int. Ed. 40 (2001) 2591-2611
9. Jenekhe S.A., and Yi S. Appl. Phys. Lett. 77 (2000) 2635-2637
10. Alam M.M., and Jenekhe S.A. Chem. Mater. 14 (2002) 4775-4780
11. Babel A., and Jenekhe S.A. Macromolecules 36 (2003) 7759-7764
12. Spanggaard H., and Krebs F.C. Sol. Energ. Mater. Sol. Cells 83 (2004) 125-146
13. Evans N.R., Devi L.S., Mak C.S.K., Watkins S.E., Pascu S.I., Kohler A., Friend R.H., Williams C.K., and Holmes A.B. J. Am. Chem. Soc. 128 (2006) 6647-6656
14. Sworakowski J., and Ulanski J. Annu. Rep. Prog. Chem., Sect. C 99 (2003) 87-125
15. Cheun H., and Winokur M.J. Synth. Met. 154 (2005) 137-140
16. Chao T.-C., Lin Y.-T., Yang C.-Y., Hung T.S., Chou H.-C., Wu C.-C., and Wong K.T. Adv. Mater. 17 (2005) 992-996
17. Tang R., Tan Z., Li Y., and Xi F. Chem. Mater. 18 (2006) 1053-1061
18. Mishra A.K., Graf M., Grasse F., Jacob J., List E.J.W., and Klaus Müllen. Chem. Mater. 18 (2006) 2879-2885
19. Wang E., Li C., Mo Y., Zhang Y., Ma G., Shi W., Peng J., Yang W., and Cao Y. J. Mater. Chem. 16 (2006) 4133-4140
20. Roncali J. Chem. Rev. 97 (1997) 173205
21. Seruga J.L. Acta Polym. 49 (1998) 319-344
22. Perepichka I.F., Perepichka D.F., Meng H., and Wudl F. Adv. Mater. 17 (2005) 2281-2305
23. Thompson B.C., Kim Y.-G., McCarley T.D., and Reynolds J.R. J. Am. Chem. Soc. 128 (2006) 12714-12725
24. Li M., Tang S., Shen F., Liu M., Xie W., Xia H., Liu L., Tian L., Xie Z., Lu P., Hanif M., Lu D., Cheng G., and Ma Y. J. Phys. Chem. B 110 (2006) 17784-17789
25. Sonmez G. Chem. Commun. (2005) 5251
26. Sirringhaus H. Adv. Mater. 17 (2005) 2411-2425
27. Sonmez G., and Sonmez H.B. J. Mater. Chem. 16 (2006) 2473-2477
28. Jenekhe S.A., Lu L., and Alam M.M. Macromolecules 34 (2001) 7315-7324
29. Wu T.-Y., and Chen Y. J. Polym. Sci. A: Polym. Chem. 40 (2002) 4452-4462
30. Cho N.S., Park J.-H., Lee S.-K., Lee J., Shim H.-K., Park M.-J., Hwang D.-H., and Jung B.-J. Macromolecules 39 (2006) 177-183
31. Kim S.-K., Lee J.-H., and Hwang D.-H. Synth. Met. 152 (2005) 201-204
32. Wu T.Y., and Chen Y. J. Polym. Sci. A: Polym. Chem. 40 (2002) 4570-4580
33. Hwang D.-H., Kim S.-K., Park M.-J., Lee J.-H., Koo B.-W., Kang I.-N., Kim S.-H., and Zyung T. Chem. Mater. 16 (2004) 1298-1303
34. Yang L., Feng J.-K., and Ren A.-M. J. Org. Chem. 70 (2005) 5987-5996
35. Sun X., Liu Y., Xu X., Yang C., Yu G., Chen S., Zhao Z., Qiu W., Li Y., and Zhu D. J. Phys. Chem. B 109 (2005) 10786-10792
36. Huang B., Li J., Jiang Z., Qin J., Yu G., and Liu Y. Macromolecules 38 (2005) 6915-6922
37. Zhu Y., Babel A., and Jenekhe S.A. Macromolecules 38 (2005) 7983-7991
38. Gooley C.M., Keyzer H., and Setchel F. Nature 223 (1969) 80
39. Patriarche G.J., and Lingane J.V. Anal. Chim. Acta 49 (1970) 25
40. Dang X.-J., Nie M.-Y., Tong J., and Li H.-L. J. Electroanal. Chem 437 (1997) 53-59
41. Higuchi A., Inada H., Kobata T., and Shiraota Y. Adv. Mater. 3 (1991) 549
42. Lai R.Y., Kong X., Jenekhe S.A., and Bard A.J. J. Am. Chem. Soc. 125 (2003) 12631-12639
43. Sailer M., Nonnenmacher M., Oeser T., and Müller T.J.J. Eur. J. Org. Chem. (2006) 423-435
44. Blankert B., Hayen H., van Leeuwen S.M., Karst U., Bodoki E., Lotrean S., Sandulescu R., Mora Diez N., Dominguez O., Arcos J., and Kauffmann J.-M. Electroanalysis 17 (2005) 1501-1510
45. Cabaj J., Idzik K., Sołoducho J., and Chyla A. Tetrahedron 62 (2006) 758-766
46. Doskocz J., Doskocz M., Roszak S., Sołoducho J., and Leszczyński J. J. Phys. Chem. A 110 (2006) 13989-13993
47. Pickup P.G. J. Mater. Chem. 9 (1999) 1641-1653
48. Holliday B.J., and Swager T.M. Chem. Commun. (2005) 23-36
49. Murray R.W. In: Bard A.J. (Ed). Electroanalytical Chemistry vol. 13 (1984), Marcel Dekker, New York p. 192
50. Abruña H.D. Coord. Chem. Rev. 86 (1988) 135
51. Murray R.W. In: Murray R.W. (Ed). Molecular Design of Electrode Surfaces (1992), Wiley, New York p. 1 (Chapter 1)
52. Colladet K., Fourier S., Cleij T.J., Lutsen L., Gelan J., Vanderzande D., Nguyen L.H., Neugebauer H., Sariciftci S., Aguirre A., Janssen G., and Goovaerts E. Macromolecules 40 (2007) 65-71
53. Parr R.G., and Yang R.W. Density-Functional Theory of Atoms and Molecules (1994), Oxford University Press, New York
54. Becke D. J. Chem. Phys. 98 (1993) 5648-5652
55. Vosko S.H., Wilk L., and Nusiar M. Can. J. Phys. 58 (1980) 1200
56. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
57. Krishnan R., Binkley J.S., Seeger R., and Pople J.A. J. Chem. Phys. 72 (1980) 650-654
58. Reed A.E., Weinstock R.B., and Weinhold F. J. Chem. Phys. 83 (1985) 735-738
59. Frisch M.J., Trucks G.W., Schlegel H.B., et al. Gaussian 03 (2004), Pittsburgh, PA (Revision C 02)
60. J. Sołoducho, J. Doskocz, J. Cabaj, Pol. Pat. P 379237, (2006).