A simple and efficient route to N-functionalized dithieno[3,2-b:2′,3′-d]pyrroles: Fused-ring building blocks for new conjugated polymeric systems

Journal of Organic Chemistry

Volumn 68, Issue 7, 2003, Pages 2921-2928

  Ogawa, Katsu ^a   Rasmussen, Seth C ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION PROCESS;

AMINATION; AMINES; CATALYST ACTIVITY; ELECTROCHEMISTRY; PALLADIUM; X RAY ANALYSIS;

ORGANIC POLYMERS;

DITHIENO[3,2:2',3' D]PYRROLE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

AMINES; CATALYSIS; CHEMISTRY, ORGANIC; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MOLECULAR CONFORMATION; PALLADIUM; POLYMERS; PYRROLES; THIOPHENES;

EID: 0037419460     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034078k     Document Type: Article

References (58)

1. The Nobel Foundation: http://www.nobel.se/chemistry/laureates/2000.
2. (a) Conjugated Conducting Polymers; Kiess, H., Ed.; Springer Series in Solid State Sciences; Springer-Verlag: New York, 1992; Vol. 102. (b) Kaner, R. B.; MacDiarmid, A. G. Sci. Am. 1988, 258 (2), 106. (c) Yam, P. Sci. Am. 1995, 271 (1), 82.
3. (a) Conjugated Conducting Polymers; Kiess, H., Ed.; Springer Series in Solid State Sciences; Springer-Verlag: New York, 1992; Vol. 102. (b) Kaner, R. B.; MacDiarmid, A. G. Sci. Am. 1988, 258 (2), 106. (c) Yam, P. Sci. Am. 1995, 271 (1), 82.
4. (a) Conjugated Conducting Polymers; Kiess, H., Ed.; Springer Series in Solid State Sciences; Springer-Verlag: New York, 1992; Vol. 102. (b) Kaner, R. B.; MacDiarmid, A. G. Sci. Am. 1988, 258 (2), 106. (c) Yam, P. Sci. Am. 1995, 271 (1), 82.
5. Baker, G. L. In Electronic and Photonic Application of Polymers; Bowden, M. J., Turner, S. R., Eds.; ACS Advances in Chemistry Series 210; American Chemical Society: Washington, DC, 1985.
6. Tourillion, G. Polythiophene and its Derivatives. In Handbook of Conducting Polymers; Skothem, T. A., Ed.; Marcel Dekker: New York, 1986.
7. (a) Roncali, J. Chem. Rev. 1992, 92,711. (b) Schopf, G.; Kossmehl, G. Adv. Polym. Sci. 1997, 129, 1. (c) Leclerc, M.; Faid, K. Adv. Mater. 1997, 9, 1087. (d) Garnier, J. Angew. Chem., Int. Ed. Engl. 1989, 28, 513.
8. (a) Roncali, J. Chem. Rev. 1992, 92,711. (b) Schopf, G.; Kossmehl, G. Adv. Polym. Sci. 1997, 129, 1. (c) Leclerc, M.; Faid, K. Adv. Mater. 1997, 9, 1087. (d) Garnier, J. Angew. Chem., Int. Ed. Engl. 1989, 28, 513.
9. (a) Roncali, J. Chem. Rev. 1992, 92,711. (b) Schopf, G.; Kossmehl, G. Adv. Polym. Sci. 1997, 129, 1. (c) Leclerc, M.; Faid, K. Adv. Mater. 1997, 9, 1087. (d) Garnier, J. Angew. Chem., Int. Ed. Engl. 1989, 28, 513.
10. (a) Roncali, J. Chem. Rev. 1992, 92,711. (b) Schopf, G.; Kossmehl, G. Adv. Polym. Sci. 1997, 129, 1. (c) Leclerc, M.; Faid, K. Adv. Mater. 1997, 9, 1087. (d) Garnier, J. Angew. Chem., Int. Ed. Engl. 1989, 28, 513.
11. Rasmussen, S. C.; Straw, B. D.; Hutchison, J. E. In Semiconducting Polymers: Applications, Synthesis, and Properties; Hsieh, B. R., Wei, W., Galvin, M., Eds.; ACS Symposium Series 735; American Chemical Society: Washington, DC, 1999.
12. (a) Roncali, J. Chem. Rev. 1997, 97, 173. (b) Pomerantz, M. In Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsen-baumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998; pp 277-309.
13. (a) Roncali, J. Chem. Rev. 1997, 97, 173. (b) Pomerantz, M. In Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsen-baumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998; pp 277-309.
14. (a) Wudl, F.; Kobayashi, M.; Heeger, A. J. J. Org. Chem. 1984, 49, 3382. (b) Kobayashi, M.; Colaneri, N.; Boysel, F.; Wudl, F.; Heeger, A. J. J. Chem. Phys. 1985, 82, 5717. (c) Colaneri, N.; Kobayashi, M.; Heeger, A. J.; Wudl, F. Synth. Met. 1986, 14, 45. (d) Ikenoue, Y.; Wudl, F.; Heeger, A. J. Synth. Met. 1991, 40, 1. (e) King, G.; Higgins, S. J. J. Mater. Chem. 1995, 5, 447.
15. (a) Wudl, F.; Kobayashi, M.; Heeger, A. J. J. Org. Chem. 1984, 49, 3382. (b) Kobayashi, M.; Colaneri, N.; Boysel, F.; Wudl, F.; Heeger, A. J. J. Chem. Phys. 1985, 82, 5717. (c) Colaneri, N.; Kobayashi, M.; Heeger, A. J.; Wudl, F. Synth. Met. 1986, 14, 45. (d) Ikenoue, Y.; Wudl, F.; Heeger, A. J. Synth. Met. 1991, 40, 1. (e) King, G.; Higgins, S. J. J. Mater. Chem. 1995, 5, 447.
16. (a) Wudl, F.; Kobayashi, M.; Heeger, A. J. J. Org. Chem. 1984, 49, 3382. (b) Kobayashi, M.; Colaneri, N.; Boysel, F.; Wudl, F.; Heeger, A. J. J. Chem. Phys. 1985, 82, 5717. (c) Colaneri, N.; Kobayashi, M.; Heeger, A. J.; Wudl, F. Synth. Met. 1986, 14, 45. (d) Ikenoue, Y.; Wudl, F.; Heeger, A. J. Synth. Met. 1991, 40, 1. (e) King, G.; Higgins, S. J. J. Mater. Chem. 1995, 5, 447.
17. (a) Wudl, F.; Kobayashi, M.; Heeger, A. J. J. Org. Chem. 1984, 49, 3382. (b) Kobayashi, M.; Colaneri, N.; Boysel, F.; Wudl, F.; Heeger, A. J. J. Chem. Phys. 1985, 82, 5717. (c) Colaneri, N.; Kobayashi, M.; Heeger, A. J.; Wudl, F. Synth. Met. 1986, 14, 45. (d) Ikenoue, Y.; Wudl, F.; Heeger, A. J. Synth. Met. 1991, 40, 1. (e) King, G.; Higgins, S. J. J. Mater. Chem. 1995, 5, 447.
18. (a) Wudl, F.; Kobayashi, M.; Heeger, A. J. J. Org. Chem. 1984, 49, 3382. (b) Kobayashi, M.; Colaneri, N.; Boysel, F.; Wudl, F.; Heeger, A. J. J. Chem. Phys. 1985, 82, 5717. (c) Colaneri, N.; Kobayashi, M.; Heeger, A. J.; Wudl, F. Synth. Met. 1986, 14, 45. (d) Ikenoue, Y.; Wudl, F.; Heeger, A. J. Synth. Met. 1991, 40, 1. (e) King, G.; Higgins, S. J. J. Mater. Chem. 1995, 5, 447.
19. (a) Pomerantz, M.; Chaloner-Gill, B.; Harding, L. O.; Tseng, J. J.; Pomerantz, W. J. J. Chem. Soc., Chem. Commun. 1992, 1672. (b) Kastner, J.; Kuzmany, H.; Vegh, D.; Landl, M.; Cuff, L.; Kertesz, M. Synth. Met. 1995, 69, 593. (c) Kastner, J.; Kuzmany, H.; Vegh, D.; Landl, M.; Cuff, L.; Kertesz, M. Macromolecules 1995, 28, 2922.
20. (a) Pomerantz, M.; Chaloner-Gill, B.; Harding, L. O.; Tseng, J. J.; Pomerantz, W. J. J. Chem. Soc., Chem. Commun. 1992, 1672. (b) Kastner, J.; Kuzmany, H.; Vegh, D.; Landl, M.; Cuff, L.; Kertesz, M. Synth. Met. 1995, 69, 593. (c) Kastner, J.; Kuzmany, H.; Vegh, D.; Landl, M.; Cuff, L.; Kertesz, M. Macromolecules 1995, 28, 2922.
21. (a) Pomerantz, M.; Chaloner-Gill, B.; Harding, L. O.; Tseng, J. J.; Pomerantz, W. J. J. Chem. Soc., Chem. Commun. 1992, 1672. (b) Kastner, J.; Kuzmany, H.; Vegh, D.; Landl, M.; Cuff, L.; Kertesz, M. Synth. Met. 1995, 69, 593. (c) Kastner, J.; Kuzmany, H.; Vegh, D.; Landl, M.; Cuff, L.; Kertesz, M. Macromolecules 1995, 28, 2922.
22. (a) Kenning, D. D.; Funfar, M. R.; Rasmussen, S. C. Polym. Prepr. 2001, 42, 506. (b) Kenning, D. D.; Mitchell, K. A.; Funfar, M. R.; Rasmussen, S. C. Polym. Prepr. 2001, 42, 665. (c) Kenning, D. D.; Ogawa, K.; Rothstein, S. D.; Rasmussen, S. C. Polym. Mater. Sci. Eng. 2002, 86, 59.
23. (a) Kenning, D. D.; Funfar, M. R.; Rasmussen, S. C. Polym. Prepr. 2001, 42, 506. (b) Kenning, D. D.; Mitchell, K. A.; Funfar, M. R.; Rasmussen, S. C. Polym. Prepr. 2001, 42, 665. (c) Kenning, D. D.; Ogawa, K.; Rothstein, S. D.; Rasmussen, S. C. Polym. Mater. Sci. Eng. 2002, 86, 59.
24. (a) Kenning, D. D.; Funfar, M. R.; Rasmussen, S. C. Polym. Prepr. 2001, 42, 506. (b) Kenning, D. D.; Mitchell, K. A.; Funfar, M. R.; Rasmussen, S. C. Polym. Prepr. 2001, 42, 665. (c) Kenning, D. D.; Ogawa, K.; Rothstein, S. D.; Rasmussen, S. C. Polym. Mater. Sci. Eng. 2002, 86, 59.
25. Pomerantz, M.; Gu, X. Synth. Met. 1997, 84, 243.
26. Tanaka, S.; Yamashita, Y. Synth. Met. 1997, 84,229.
27. (a) Jow, T. R.; Jen, K. Y.; Elsenbaumer, R. L.; Shacklette, L. W.; Angelopoulos, M.; Cava, M. P. Synth. Met. 1986, 14, 53. (b) Danieli, R.; Taliani, C.; Zamboni, R.; Giro, G.; Biserni, M.; Mastragostino, M.; Testoni, A. Synth. Met. 1986, 13, 325. (c) Taliani, C.; Zamboni, R.; Danieli, R.; Ostoja, P.; Porzio, W.; Lazzaroni, R.; Bredas, J. L. Phys. Scr. 1989, 40, 781. (d) Bolognesi, A.; Catellani, M.; Destri, S.; Porzio, W.; Taliani, C.; Zamboni, R. Mol. Cryst. Liq. Crst. 1990, 187, 519.
28. (a) Jow, T. R.; Jen, K. Y.; Elsenbaumer, R. L.; Shacklette, L. W.; Angelopoulos, M.; Cava, M. P. Synth. Met. 1986, 14, 53. (b) Danieli, R.; Taliani, C.; Zamboni, R.; Giro, G.; Biserni, M.; Mastragostino, M.; Testoni, A. Synth. Met. 1986, 13, 325. (c) Taliani, C.; Zamboni, R.; Danieli, R.; Ostoja, P.; Porzio, W.; Lazzaroni, R.; Bredas, J. L. Phys. Scr. 1989, 40, 781. (d) Bolognesi, A.; Catellani, M.; Destri, S.; Porzio, W.; Taliani, C.; Zamboni, R. Mol. Cryst. Liq. Crst. 1990, 187, 519.
29. (a) Jow, T. R.; Jen, K. Y.; Elsenbaumer, R. L.; Shacklette, L. W.; Angelopoulos, M.; Cava, M. P. Synth. Met. 1986, 14, 53. (b) Danieli, R.; Taliani, C.; Zamboni, R.; Giro, G.; Biserni, M.; Mastragostino, M.; Testoni, A. Synth. Met. 1986, 13, 325. (c) Taliani, C.; Zamboni, R.; Danieli, R.; Ostoja, P.; Porzio, W.; Lazzaroni, R.; Bredas, J. L. Phys. Scr. 1989, 40, 781. (d) Bolognesi, A.; Catellani, M.; Destri, S.; Porzio, W.; Taliani, C.; Zamboni, R. Mol. Cryst. Liq. Crst. 1990, 187, 519.
30. (a) Jow, T. R.; Jen, K. Y.; Elsenbaumer, R. L.; Shacklette, L. W.; Angelopoulos, M.; Cava, M. P. Synth. Met. 1986, 14, 53. (b) Danieli, R.; Taliani, C.; Zamboni, R.; Giro, G.; Biserni, M.; Mastragostino, M.; Testoni, A. Synth. Met. 1986, 13, 325. (c) Taliani, C.; Zamboni, R.; Danieli, R.; Ostoja, P.; Porzio, W.; Lazzaroni, R.; Bredas, J. L. Phys. Scr. 1989, 40, 781. (d) Bolognesi, A.; Catellani, M.; Destri, S.; Porzio, W.; Taliani, C.; Zamboni, R. Mol. Cryst. Liq. Crst. 1990, 187, 519.
31. Kumagai, T.; Tanaka, S.; Mukai, T. Tetrahedron Lett. 1984, 25, 5669.
32. Lazzaroni, R.; Riga, J.; Verbist, J. J.; Christiaens, L.; Renson, M. J. Chem. Soc., Chem. Commun. 1985, 999.
33. (a) Berlin, A.; Pagani, G.; Zotti, G.; Schiavon, G. Makromol. Chem. 1992, 193, 399. (b) Pagani, G. A. Heterocycles 1994, 37, 2069.
34. (a) Berlin, A.; Pagani, G.; Zotti, G.; Schiavon, G. Makromol. Chem. 1992, 193, 399. (b) Pagani, G. A. Heterocycles 1994, 37, 2069.
35. Ogawa, K.; Radke, K. R.; Rothstein, S. D.; Rasmussen, S. C. J. Org. Chem. 2001, 66, 9067.
36. Zanirato, P.; Spagnolo, P.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1983, 2551.
37. Jordens, P.; Rawson, G.; Wynberg, Hans, J. Chem. Soc. C 1970, 2,273 2, 273.
38. Kenning, D. D.; Mitchell, K. A.; Calhoun, T. R.; Funfar, M. R.; Sattler, D. J.; Rasmussen, S. C. J. Org. Chem. 2002, 67, 9073.
39. Cox, E. G.; Gillot, R. J. J. H.; Jeffrey, G. A. Acta Crystallogr. 1949, 2, 356.
40. Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2nd ed.; Pergamon: New York, 2000; pp 61, 80-81.
41. Barbarella, G.; Zambianchi, M.; Antolini, L.; Folli, U.; Goldoni, F.; larossi, D.; Schenetti, L.; Bongini, A. J. Chem. Soc., Perkin Trans. 2 1995, 1869.
42. CRC Handbook of Chemistry and Physics; Lide, D. R., Frederikse, H. P. R., Eds.; CRC Press: Boca Raton, FL, 1995; p 9-4.
43. Buemi, G. J. Chim. Phys. Phys. Chim. Biol. 1987, 84, 1147.
44. Audebert, P.; Hapiot, P. Synth. Met. 1995, 75, 95.
45. (a) Diaz, A. F.; Castillo, J.; Kanazawa, K. K.; Logan, J. A.; Salmon, M.; Fajardo, O. J. Electroanal. Chem. 1982, 133, 233. (b) Ferraris, J. P.; Guerrero, D. J. In Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998; pp 259-76.
46. (a) Diaz, A. F.; Castillo, J.; Kanazawa, K. K.; Logan, J. A.; Salmon, M.; Fajardo, O. J. Electroanal. Chem. 1982, 133, 233. (b) Ferraris, J. P.; Guerrero, D. J. In Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998; pp 259-76.
47. Calculations were performed using SPARTAN (Wavefunction, Inc.) by ab initio (HF STO-3G) methods.
48. Gleiter, R.; Kobayshi, M.; Spanget-Larsen, J.; Gronowitz, S.; Konar, A.; Farnier, M. J. Org. Chem. 1977, 42, 2230.
49. Aratani, T.; Yoshihara, H.; Suzukamo, G. Tetrahedron Lett. 1989, 30, 1655.
50. Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2nd ed.; Pergamon: New York, 2000; pp 68-9.
51. Fujitsuka, M.; Sato, T.; Sezaki, F.; Tanaka, K.; Watanabe, A.; Ito, 0. J. Chem. Soc., Faraday Trans. 1998, 94, 3331.
52. Hinman, R. L.; Theodoropulos, S. J. Org. Chem. 1963, 28, 3052.
53. Schofield, K. Hetero-Aromatic Nitrogen Compounds. Pyrroles and Pyridines; Plenum Press: New York, 1967; pp 51-58.
54. Becker, R. S.; de Melo, J. S.; Macanita, A. L.; Elisei, F. J. Phys. Chem. 1996, 100, 18683.
55. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991; pp 86-90.
56. Larson, R. C.; Iwamoto, R. T.; Adams, R. N. Anal. Chim. Acta 1961, 25, 371.
57. (a) Standards in Fluorescence Spectrometry; Miller, J. N., Ed.; Chapman and Hall: New York, 1981; pp 68-78. (b) Handbook of Organic Photochemistry; Scaiano, J. C., Ed.; CRC Press: Boca Raton, FL, pp 233-236.
58. (a) Standards in Fluorescence Spectrometry; Miller, J. N., Ed.; Chapman and Hall: New York, 1981; pp 68-78. (b) Handbook of Organic Photochemistry; Scaiano, J. C., Ed.; CRC Press: Boca Raton, FL, pp 233-236.