Redox chemistry of bipyrroles: Further insights into the oxidative polymerization mechanism of pyrrole and oligopyrroles

Journal of Physical Chemistry B

Volumn 101, Issue 29, 1997, Pages 5698-5706

  Guyard, Laurent ^a   Hapiot, Philippe ^b   Neta, Pedatsur ^c  

^a UNIVERSITÉ DE FRANCHE COMTÉ   (France)

^b UNIVERSITÉ PARIS DIDEROT   (France)

^c NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; AROMATIC POLYMERS; CARBON TETRACHLORIDE; ELECTROCHEMISTRY; FREE RADICALS; OLIGOMERS; OXIDATION; PH EFFECTS; PHOTOLYSIS; POLYMERIZATION; REDOX REACTIONS; ULTRAVIOLET RADIATION;

FLASH PHOTOLYSIS; POLYPYRROLES; PULSE RADIOLYSIS;

CONDUCTIVE PLASTICS;

EID: 0031190885     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp9706083     Document Type: Article

References (71)

1. (a) Bäuerle, P. Adv. Mater. 1993, 5, 879.
2. (b) Tour, J.-M. Chem. Rev. (Washington, D.C.) 1996, 96, 537.
3. (a) Andrieux, C. P.; Audebert, P.; Hapiot, P.; Savéant, J.-M. J. Am. Chem. Soc, 1990, 112, 2439.
4. (b) Andrieux, C. P.; Audebert, P.; Hapiot, P.; Savéant, J.-M. J. Phys. Chem. 1991, 95, 10158.
5. Génies, E. M.; Bidan, G.; Diaz, A. F. J. Electroanal. Chem. 1983, 149, 101.
6. (a) Schichiri, T.; Toriumi, M.; Tanaka, K.; Yamabe, T.; Yamauchi, J.; Deguchi, Y. Synth. Met. 1989, 33, 389.
7. (b) Lowen, S. V.; Van Dyke, J. D. J. Polym. Sci., Part A: Polym. Chem. 1990, 28, 451.
8. (a) Satoh, M.; Imanishi, K.; Yoshino, K. J. Electroanal. Chem. 1991, 317, 139.
9. (b) Wei, Y.; Chan, C. C.; Tian, J.; Jang, G. W.; Hsueh, K. F. Chem. Mater. 1991, 3, 888.
10. 3b
11. (a) Zotti, G.; Schiavon, G.; Berlin, A.; Pagani, G. Chem. Mater. 1993, 5, 430.
12. (b) Niziurski-Mann, R. E.; Scordilis-Kelley, C.; Liu, T.-L.; Cava, M. P.; Carlin, R. T. J. Am. Chem. Soc. 1993, 115, 887.
13. (c) Audebert, P.; Catel, J.-M.; Le Coustumer, G.; Duchenet, V.; Hapiot, P. J. Phys. Chem. 1995, 99, 11923.
14. (d) Hapiot, P.; Gaillon, L.; Audebert, P.; Moreau, J. J. E.; Lère-Porte, J.-P.; Wong Chi Man, M. J. Electroanal. Chem., in press.
15. (a) Martina, S.; Elkelmann, V.; Schlüter, A.-D.; Wegner, G. Synth. Met. 1992, 51, 299.
16. (b) Groenendaal, L.; Peerlings, H. W. I.; Van Dongen, J. L. J.; Havinga, E. E.; Vekemans, J. A. J. M.; Meijer, E. W. Macromolecules 1995, 28, 116.
17. (c) Groenendaal, L.; Peerlings, H. W. I.; Havinga, E. E.; Vekemans, J. A. J. M.; Meijer, E. W. Synth. Met. 1995, 69, 467.
18. (a) Zotti, G.; Martina, S.; Wegner, G.; Schlüter, A.-D. Adv. Mater. 1992, 4, 798.
19. (b) Van Haare, J. A. E. H.; Groenendaal, L.; Peerlings, H. W. I.; Havinga, E. E.; Vekemans, J. A. J. M.; Janssen, R. A. J.; Meijer, E. W. Chem. Mater. 1995, 7, 1984.
20. (c) Van Haare, J. A. E. H.; Groenendaal, L.; Havinga, E. E.; Janssen, R. A. J.; Meijer, E. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 638.
21. (d) Andrieux, C. P.; Hapiot, P.; Audebert, P.; Guyard L.; Nguyen Dinh An, M.; Groenendaal, L.; Meijer, E. W. Chem. Mater. 1997, 9, 723.
22. Jones, R. A. The Chemistry of Pyrroles; Academic Press: New York, 1977; p 11.
23. (a) Diaz, A. F.; Kanazawa, K. K.; Gardini, G. P. J. Chem. Soc., Chem. Commun. 1979, 635.
24. (b) Downard, A. J.; Pletcher, D. J. Electroanal. Chem. 1986, 206, 139.
25. (c) Zotti, G.; Schiavon, G.; Berlin, A.; Pagani, G. Electrochim. Acta 1989, 34, 881.
26. (d) Beck, F.; Oberst, M.; Janssen, R. Electrochim. Acta 1990, 35, 1841.
27. (e) Qian, R.; Pei, Q.; Huang, Z. Makromol. Chem. 1991, 192, 1263.
28. (f) Raymond, D. E.; Harrison, D. J. J. Electroanal. Chem. 1993, 355, 115.
29. (a) Downard, A. J.; Pletcher, D. J. Electroanal. Chem. 1986, 206, 147.
30. (b) Visy, C.; Lukkari, J.; Kankare, J. Synth. Met. 1994, 66, 61.
31. (a) Anne, A.; Hapiot, P.; Moiroux, J.; Neta, P.; Savéant, J.-M. J. Phys. Chem. 1991, 95, 2370.
32. (b) Anne, A.; Fraoua, S.; Hapiot, P.; Moiroux, J.; Savéant, J.-M. J. Am. Chem. Soc. 1995, 117, 7412.
33. (a) Evans, C. H.; Scaiano, J. C. J. Am. Chem. Soc. 1990, 112, 2694.
34. (b) Zinger, B.; Mann, K. R.; Hill, M. G.; Miller, L. L. Chem. Mater. 1992, 4, 1113.
35. (c) Wintgens, V.; Valat, P.; Garnier, F. J. Phys. Chem. 1994, 98, 228.
36. The mention of commercial equipment or material does not imply recognition or endorsement by the National Institute of Standards and Technology nor does it imply that the material or equipment identified are necessarily the best available for the purpose.
37. Neta, P.; Huie, R. E. J. Phys. Chem. 1985, 89, 1783.
38. Schuler, R. H.; Patterson, L. K.; Janata, E. J. Phys. Chem. 1980, 84, 2088.
39. Garreau, D.; Savéant, J.-M. J. Electroanal. Chem. 1972, 35, 309.
40. (a) Andrieux, C. P.; Garreau, D.; Hapiot, P.; Pinson, J.; Savéant, J.-M. J. Electroanal. Chem. 1988, 243, 321.
41. (b) Andrieux, C. P.; Hapiot, P.; Savéant, J.-M. Chem. Rev. (Washington, D.C.) 1990, 90, 723.
42. (c) Lexa, D.; Savéant, J.-M.; Zickler, J. J. Am. Chem. Soc. 1977, 99, 2786.
43. Miller, L. L.; Mann, K. R. Ace. Chem. Res. 1996, 29, 417.
44. 22b,c
45. (b) Andrieux, C. P.; Nadjo, L.; Savéant, J.-M. J. Electroanal Chem. 1973, 42, 223.
46. (c) Nadjo, L.; Savéant, J.-M. J. Electroanal. Chem. 1973, 48, 113.
47. Stanbury, D. M. Adv. Inorg. Chem. 1989, 33, 69.
48. 24d
49. (b) Bent, D. V.; Hayon, E. J. Am. Chem. Soc. 1975, 97, 2612.
50. (c) Shen, X.; Lind, J.; Merényi, G. J. Phys. Chem. 1987, 91, 4403.
51. (d) Bent, D. V.; Hayon, E.; Moorthy, P. N. Chem. Phys. Lett. 1974, 27, 544.
52. -1) (mechanism CR-S).
53. It should be noted that, because of the low oxidation potential of quaterpyrroles, it is difficult to make conclusions if the oxidation of the dimer is related to the photochemical process or to subsequent oxidation under air.
54. Audebert, P.; Catel, J.-M.; Le Coustumer, G.; Duchenet, V.; Hapiot, P. In preparation.
55. Möning, J.; Bahnemann, D.; Asmus, K. D. Chem. Biol. Interact. 1983, 47, 15.
56. 29b
57. (b) Merényi, G.; Lind, J.; Engman, L. J. Chem. Soc., Perkin Trans. 2 1994, 2551.
58. Bäuerle, P.; Segelbacher, U.; Maier, A.; Mehring, M. J. Am. Chem. Soc. 1993, 115, 10217.
59. (a) Zotti, G.; Martina, S.; Wegner, G.; Schlüter, A.-D. Adv. Mater. 1992, 4, 798.
60. (b) Hapiot, P.; Audebert, P.; Monnier, K.; Pernaut, J.-M.; Garcia, P. Chem. Mater. 1994, 6, 1549.
61. (a) Potts, H. A.; Smith, G. F. J. Chem. Soc. 1957, 4018.
62. (b) Naqvi N.; Fernando, Q. J. Org. Chem. 1960, 25, 551.
63. (c) Chiang, Y.; Whipple, E. B. J. Am. Chem. Soc. 1963, 85, 26.
64. (d) Chiang, Y.; Whipple, E. B. J. Am. Chem. Soc. 1963, 85, 2763.
65. (e) Smith, G. F. Adv. Heterocycl. Chem. 1963, 2, 287.
66. Spectroelectrochemical experiments indicate that the yield of produce dimethylquaterpyrrole is higher than 70% (see Figure 2).
67. (a) See, for example, refs 14b and 34b and references therein,
68. (b) Hapiot, P.; Lorcy, D.; Tallec, A.; Carrier, R.; Robert, A. J. Phys. Chem. 1996, 100, 14823.
69. When 1% of water was added to the solution, little change was found in the voltammogram of MBP, just a small increase of the wave of the produced dimethylquaterpyrrole.
70. (a) See, for example, ref 36b and references therein,
71. (b) Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 7472.