Poly(3,4-alkylenedioxypyrroles): The PXDOPs as versatile yet underutilized electroactive and conducting polymers

Advanced Materials

Volumn 18, Issue 9, 2006, Pages 1121-1131

  Walczak, Ryan M ^a,b   Reynolds, John R ^a,b,c  

^a University of Florida ^*  (United States)

^b UNIVERSITY OF FLORIDA   (United States)

^c University of Florida   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROACTIVE POLYMERS; POLY(3,4-DIOXYPYRROLE) (PXDOP); REDOX PROPERTIES;

ACTUATORS; CHEMICAL SENSORS; ELECTROCHROMISM; OPTOELECTRONIC DEVICES; SWITCHING SYSTEMS; SYNTHESIS (CHEMICAL);

POLYPYRROLES;

EID: 33646505972     PISSN: 09359648     EISSN: None     Source Type: Journal    
DOI: 10.1002/adma.200502312     Document Type: Review

References (55)

1. J. L. Reddinger, J. R. Reynolds, Adv. Polym. Sci. 1999, 145, 57.
2. R. D. McCullough, Adv. Mater. 1998, 10, 93.
3. A. Moliton, R. C. Hiorns, Polym. Int. 2004, 53, 1397.
4. J. W. Schultze, H. Karabulut, Electrochim. Acta 2005, 50, 1739.
5. L. Groenendaal, G. Zotti, P.-H. Aubert, S. Waybright, J. R. Reynolds, Adv. Mater. 2003, 15, 855.
6. A. Cirpan, A. A. Argun, C. R. G. Grenier, B. D. Reeves, J. R. Reynolds, J. Mater. Chem. 2003, 13, 2422.
7. A. A. Argun, P.-H. Aubert, B. C. Thompson, I. Schwendeman, C. L. Gaupp, J. Hwang, N. J. Pinto, D. B. Tanner, A. G. MacDiarmid, J. R. Reynolds, Chem. Mater. 2004, 16, 4401.
8. G. Gigli, O. Inganas, M. Anni, M. De Vittorio, R. Cingolani, G. Barbarella, L. Favaretto, Appl. Phys. Lett. 2001, 78, 1493.
9. I. Perepichka, D. Perepichka, H. Meng, F. Wudl, Adv. Mater. 2005, 77, 2281.
10. L. B. Groenendaal, F. Jonas, D. Freitag, H. Pielartzik, J. R. Reynolds, Adv. Mater. 2000, 12, 481.
11. C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, Adv. Funct. Mater. 200l, 11, 15.
12. D. T. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537.
13. J. L. Reddinger, J. R. Reynolds, Chem. Mater. 1998, 10, 3.
14. J. L. Reddinger, J. R. Reynolds, Macromolecules 1997, 30, 673.
15. J. Roncali, J. Mater. Chem. 1999, 9, 1875.
16. E. Smela, Adv. Mater. 2003, 15, 481.
17. J.-M. Pernaut, J. R. Reynolds, J. Phys. Chem. B 2000, 104, 4080.
18. T.-A. Chen, R. D. Rieke, J. Am. Chem. Soc. 1992, 114, 10087.
19. R. D. McCullough, R. D. Lowe, J. Chem. Soc., Chem. Commun. 1992, 70.
20. R. D. McCullough, R. D. Lowe, M. Jayaraman, D. L. Anderson, J. Org. Chem. 1993, 58, 904.
21. R. D. McCullough, S. Tristram-Nagle, S. P. Williams, R. D. Lowe, M. Jayaraman, J. Am. Chem. Soc. 1993, 115, 4910.
22. R. S. Loewe, S. M. Khersonsky, R. D. McCullough, Adv. Mater. 1999, 11, 250.
23. R. S. Loewe, P. C. Ewbank, J. S. Liu, L. Zhai, R. D. McCullough, Macromolecules 2001, 34, 4324.
24. Note that any abbreviation in this document beginning with the letter "P" refers to the polymeric form of the molecule. For example, "PEDOT" is the abbreviated form of "poly(EDOT)".
25. G. Heywang, F. Jonas, Adv. Mater. 1992, 4, 116.
26. A. Kumar, D. M. Welsh, M. C. Morvant, F. Piroux, K. A. Abboud, J. R. Reynolds, Chem. Mater. 1998, 10, 896.
27. K. Doblhofer, K. Rajeshwar, in Handbook of Conducting Polymers, 2nd ed. (Eds: T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds), Marcel Dekker, New York 1998, p. 531.
28. J. H. Kaufman, N. Colaneri, J. C. Scott, G. B. Street, Phys. Rev. Lett. 1984, 53, 1005.
29. G. Leising, S. Tasch, W. Graupner, in Handbook of Conducting Polymers, 2nd ed. (Eds: T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds), Marcel Dekker, New York 1998, p. 847.
30. M. Pomerantz, in Handbook of Conducting Polymers, 2nd ed. (Eds: T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds), Marcel Dekker, New York 1998, p. 277.
31. Note that concepts of "low," "mid," and "high" are relative, but low bandgap is roughly defined as <2.0 eV, high bandgap as >3.0 eV, low oxidation potential as < 0.5 V versus SCE, and high oxidation potential as > 0.5 V versus SCE.
32. A. Merz, R. Schwarz, R. Schropp, Adv. Mater. 1992, 4, 409.
33. A. Merz, R. Schropp, E. Dotterl, Synthesis 1995, 795.
34. K. Zong, J. R. Reynolds, J. Org. Chem. 2001, 66, 6873.
35. C. L. Gaupp, K. Zong, P. Schottland, B. C. Thompson, C. A. Thomas, J. R. Reynolds, Macromolecules 2000, 33, 1132.
36. C. A. Thomas, K. Zong, P. Schottland, J. R. Reynolds, Adv. Mater. 2000, 12, 222.
37. P. Schottland, K. Zong, C. L. Gaupp, B. C. Thompson, C. A. Thomas, I. Giurgiu, R. Hickman, K. A. Abboud, J. R. Reynolds, Macromolecules 2000, 33, 7051.
38. E. W. Fager, J. Am. Chem. Soc. 1945, 67, 2217.
39. K. Zong, L. B. Groenendaal, J. R. Reynolds, unpublished.
40. T. Murashima, Y. Uchihara, N. Wakamori, H. Uno, T. Ogawa, N. Ono, Tetrahedron Lett. 1996, 37, 3133.
41. A. Merz, T. Meyer, Synthesis 1999, 94.
42. I. T. Kim, J. Y. Lee, S. W. Lee, Chem. Lett. 2004, 55, 46.
43. A. Merz, S. Graf, J. Electroanal. Chem. 1996, 412, 11.
44. G. Soenmez, I. Schwendeman, P. Schottland, K. Zong, J. R. Reynolds, Macromolecules 2003, 56, 639.
45. F. Larmat, J. R. Reynolds, B. A. Reinhardt, L. L. Brott, S. I. Clarson, J. Polym. Sci., Part A: Polym. Chem. 1997, 55, 3627.
46. C. A. Thomas, K. Zong, K. A. Abboud, P. J. Steel, J. R. Reynolds, J. Am. Chem. Soc. 2004, 126, 16440.
47. T. Murashima, K. Hirai, Y. Une, Y. Uchihara, H. Uno, N. Ono, Tetrahedron Lett. 1998, 39, 5397.
48. B. C. Thompson, P. Schottland, K. Zong, J. R. Reynolds, Chem. Mater. 2000, 12, 1563.
49. I. Schwendeman, R. Hickman, G. Soenmez, P. Schottland, K. Zong, D. M. Welsh, J. R. Reynolds, Chem. Mater. 2002, 14, 3118.
50. G. Zotti, S. Zecchin, G. Schiavon, L. Groenendaal, Chem. Mater. 2000, 12, 2996.
51. J. R. Reynolds, K. Zong, I. Schwendeman, G. Sonmez, P. Schottland, A. A. Argun, P.-H. Aubert, US Patent 6 791 738, 2004.
52. H. Yamamoto, M. Oshima, M. Koga, JP Patent 2002-134363, 2002.
53. D. J. Savage, B. A. Schell, B. K. Brady, US Patent 5 665 498, 1997.
54. C. Bohn, S. Sadki, A. B. Brennan, J. R. Reynolds, J. Electrochem. Soc. 2002, 149, E281.
55. B. Vercelli, S. Zecchin, N. Comisso, G. Zotti, A. Berlin, E. Dalcanale, L. B. Groenendaal, Chem. Mater. 2002, 14, 4768.