3,3′- and 4,4′-dimethoxy-2,2′-bipyrroles: Highly electron-rich model compounds for polypyrrole formation

Chemistry - A European Journal

Volumn 9, Issue 2, 2003, Pages 449-455

  Merz, Andreas ^a   Anikin, Sergiy ^a   Lieser, Bernd ^a   Heinze, Jürgen ^b   John, Hermann ^b  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Cyclic voltammetry; Oxidation; Polypyrrole formation; Pyrrole dimerization; Reductive N benzyl cleavage; Ullmann coupling

Indexed keywords

CARBOXYLIC ACIDS; ISOMERS; LIQUEFIED GASES; OXIDATION;

OXIDATION POTENTIAL;

POLYPYRROLES;

3,3' DIMETHOXY 2,2' BIPYRROLE DERIVATIVE; 4,4' DIMETHOXY 2,2' BIPYRROLE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; N BENZYL 3 HYDROXYPYRROLE 2,4 DICARBOXYLIC ACID; NICKEL CHLORIDE; POLYPYRROLE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIC POTENTIOMETRY; DIMERIZATION; ISOMERISM; LITHIATION; OXIDATION REDUCTION POTENTIAL;

EID: 0037455144     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390047     Document Type: Article

References (46)

1. A. F. Diaz, J. I. Castello, J. Chem. Soc. Chem. Commun. 1980, 397-398.
2. Source: Sci-Finder, Chemical Abstracts Service, American Chemical Society, February 2002.
3. J. Roncali, J. Chem. Rev. 1992, 92, 711-738.
4. a) J. Heinze, M. Dietrich, Synth. Met. 1991, 41-43, 503-506;
5. b) J. Heinze, M. Dietrich, DECHEMA-Monogr. 1990, 121, 125-130.
6. P. Tschuncky, J. Heinze. Synth. Met. 1993, 55-57, 1603-1607.
7. a) G. Heywang, F. Jonas, Adv. Mater. 1992. 4, 116-118;
8. b) M. Dietrich, J. Heinze, G. Heywang, F. Jonas, J. Electroanal. Chem. 1994, 369, 87-92.
9. L. Groenendaal, F. Jonas, D. Freitag, H. Pielartzik, J. R. Reynolds, Adv. Mater. 2000, 12, 481-494.
10. A. Merz, R. Schwarz, R. Schropp, Adv. Mater, 1992, 4, 409-411: A. Merz, S. Graf, J. Electroanal. Chem. 1996, 412, 11-17.
11. A. Merz, R. Schwarz. R. Schropp, Adv. Mater, 1992, 4, 409-411: A. Merz, S. Graf, J. Electroanal. Chem. 1996, 412, 11-17.
12. S. Graf, A. Merz, F. Gassner in Elektrochemie der lonenleiter, Vol. 3, (Ed.: F. Beck) GDCh-Monographie, 1996, pp. 547-548;
13. b) C. L. Gaupp, K. Zong, P. Schottland, B. C. Thompson, C. A. Thomas, J. R. Reynolds, Macromolecules, 2000, 33, 1132-1133.
14. G. Zotti, S. Zecchin, G. Schiavon, L. Bert Groenendaal, Chem. Mater. 2000, 2996-3005.
15. P Bäuerle, G, Gütz, A. Synowczyk, J. Heinze, Liebigs. Ann. 1996, 279-285.
16. A. Smie, A. Synowczyk, J. Heinze, R. Alle, P. Tschuncky, G. Götz, P. Bäuerle, J. Electroanal. Chem. 1998, 452, 87-95.
17. J. Heinze, H. John, M. Dietrich, P. Tschuncky, Synth. Met. 2001, 119, 49-52.
18. T. Momose, T. Tanaka, T. Yokota, N. Nagamoto, K. Yamada, Chem. Pharm. Bull. 1978, 26, 2224-2232.
19. a) J. A. Blake, H. McNab, L. Monahan. J. Chem. Soc. Perkin II, 1998, 1455-1458;
20. b) H. McNab, L. Monahan, J. Chem. Soc. Perkin Trans. II 1998, 1458-1461.
21. J. A. Blake, H. McNab, L. Monahan, J. Chem. Soc. Perkin II 1998, 1463-1468.
22. 2 = 0.052. Data collection was on a STOE-IPDS diffractometer, method: rotation, T= 173 K, λ = 0.71073, graphite monochromator. CCDC-187623 (3) and CCDC-187624 (10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge' via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+ 44)1223-336-033; or deposit@ccdc.cam.uk)
23. R. Chong, P. S. Clezy, Aust. J. Chem. 1967, 20, 935-950.
24. K. S. Kochhar, H. W. Pinnick, J. Org. Chem. 1984, 49, 3222-3226.
25. A. Merz, R. Schropp, E. Dötterl, Synthesis 1995, 795-800.
26. A. Merz, T. Meyer, Synthesis, 1999, 94-99.
27. D. L. Boger, R. R. Coleman, J. S. Panek, F. X. Huber, J. Sauer, J. Am. Chem. Soc. 1985, 107, 5377-5379.
28. T. Kaufmann, L. Lexy, Chem. Ber 1981, 114, 3674-3683.
29. L. J. Sessler, M. Cyr, A. K. Burrell, Tetrahedron 1992, 48, 9661-9672.
30. T. Momose, T. Tanaka, T. Yokota, N. Nagamoto, K. Yamada, Chem. Pharm. Bull. 1978, 26, 3521-3529.
31. P. E. Fanta, Synthesis 1974, 9; L. Groenendaal, H. W. I. Peerings, J. L. van Dongen, E. E. Havinga, J. A. J. M. Vekemans, E. W. Meijer, Macromolecules 1995, 28, 116-123.
32. P. E. Fanta, Synthesis 1974, 9; L. Groenendaal, H. W. I. Peerings, J. L. van Dongen, E. E. Havinga, J. A. J. M. Vekemans, E. W. Meijer, Macromolecules 1995, 28, 116-123.
33. A. Merz, J. Kronberger, L. Dunsch, A. Neudeck, A. Petr, L. Parkanyi, Angew. Chem. 1999, 111, 1533-1538; Angew. Chem. Int. Ed. Engl., 1999, 38, 1442-1446.
34. A. Merz, J. Kronberger, L. Dunsch, A. Neudeck, A. Petr, L. Parkanyi, Angew. Chem. 1999, 111, 1533-1538; Angew. Chem. Int. Ed. Engl., 1999, 38, 1442-1446.
35. S. Baroni, R. Sradi, M. C. Saccarallo, J. Heterocyl. Chem. 1980, 17, 1221-1223.
36. M. Matsuoka, M. Mitsuhata, T. Kitao, K. Konishi, Kogyo Kagaku Zasshi 1971, 74, 440-444.
37. a) H. Bauer, Chem. Ber. 1967, 100, 1704-1709;
38. b) H. Bauer, Chem. Ber. 1968, 101, 1286-1290.
39. a) H. Bauer, Angew. Chem. 1968, 80, 758, Angew. Chem. Int. Ed. Engl. 1968, 7, 734;
40. a) H. Bauer, Angew. Chem. 1968, 80, 758, Angew. Chem. Int. Ed. Engl. 1968, 7, 734;
41. b) H. Bauer. Liebigs Ann. Chem. 1970, 736, 1-15;
42. c) G. Pfeiffer, H. Bauer. Liebigs Ann. Chem. 1980, 564-589.
43. a) M. Zhou, J. Heinze, Electrochim. Acta 1999, 44, 1733-1748;
44. b) M. Zhou. J. Heinze, J. Phys. Chem. B 1999. 103, 8443-8450.
45. M. Zhou, M. Pagels, B. Geschke, J. Heinze, J. Phys. Chem. B 2002, 106, 10065-10073.
46. E. Lorthiois, I. Marek, J. F. Normant, J. Org. Chem. 1998, 63, 2442-2450.