Design and synthesis of a 256-membered π-conjugated oligomer library of regioregular head-to-tail coupled quater(3-arylthiophene)s

Journal of Combinatorial Chemistry

Volumn 4, Issue 5, 2002, Pages 457-469

  Briehn, Christoph A ^a   Bäuerle, Peter ^a  

^a UNIVERSITY OF ULM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 19044373610     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc010088s     Document Type: Article

References (61)

1. For review, see the following. (a) Jandeleit, B.; Schaefer, D. J.; Powers, T. S.; Turner, H. W.; Weinberg, W. H. Angew. Chem., Int. Ed. 1999, 38, 2494-2532.
2. (b) Senkan, S. Angew. Chem., Int. Ed. 2001, 40, 312-329.
3. (a) Brocchini, S.; James, K.; Tangpasuthadol, V.; Kohn, J. J. Am. Chem. Soc. 1997, 119, 4553-4554.
4. (b) Graven, D. J.; Datta, A.; Wentworth, P.; Janda, K. D. J. Am. Chem. Soc. 1998, 120, 9481-9495.
5. (c) Lewandowski, K.; Murer, P.; Svec, F.; Fréchet, J. M. J. J. Comb. Chem. 1999, 1, 105-112.
6. Wang, Y.; Li, T. Anal. Chem. 1999, 71, 4178-4182.
7. (a) Briehn, C. A.; Schiedel, M.-S.; Bonsen, E. M.; Schuhmann, W.; Bäuerle, P. Angew. Chem., Int. Ed. 2001, 40, 4680-4683.
8. (b) Schiedel, M.-S.; Briehn, C. A.; Bäuerle, P. Angew. Chem., Int. Ed. 2001, 40, 4677-4680.
9. Anderson, S. Chem. - Eur. J. 2001, 7, 4706-4714.
10. (a) Schmitz, C.; Pöschn, P.; Thelakkat, M.; Schmidt, H.-W. Phys. Chem. Chem. Phys. 1999, 1, 1777-1781.
11. (b) Schmitz, C.; Thelakkat, M.; Schmidt, H.-W. Adv. Mater. 1999, 11, 821-826.
12. Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998 and literature cited therein.
13. Sirringhaus, H.; Brown, J. P.; Friend, R. H.; Nielsen, M. M.; Beechgard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P.; deLeeuw, D. M. Nature 1999, 401, 685-688.
14. For review, see the following. Mitschke, U.; Bäuerle, P. J. Mater. Chem. 2000, 10, 1471-1507.
15. (a) Martin, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 1350-1377.
16. (b) Electronic Materials: The Oligomer Approach; Müllen, K., Wegner, G., Eds.; Wiley-VCH: New York, 1998.
17. For review, see the following. Briehn, C. A.; Bäuerle, P. Chem. Commun. 2002, 1015-1023.
18. (a) Nelson, J. C.; Young, J. K.; Moore, J. S. J. Org. Chem. 1996, 61, 8160-8168.
19. (b) Malenfant, P. R. L.; Fréchet, J. M. J. Chem. Commun. 1998, 2657-2658.
20. (c) Huang, S.; Tour, J. M. J. Org. Chem. 1999, 64, 8898-8906.
21. (d) Kirschbaum, T.; Briehn, C. A.; Bäuerle, P. J. Chem. Soc., Perkin Trans. 1 2000, 1211-1216.
22. (e) Briehn, C. A.; Kirschbaum, T.; Bäuerle, P. J. Org. Chem. 2000, 65, 352-359.
23. (f) Briehn, C. A.; Bäuerle, P. Synth. Met. 2001, 119, 121-122.
24. Roncali, J. Chem. Rev. 1997, 97, 173-205.
25. Tour, J. M.; Wu, R. Macromolecules 1992, 25, 1901-1907.
26. Mitschke, U.; Bäuerle, P. J. Chem. Soc., Perkin Trans. 1 2001, 740-753.
27. (a) Kankare, J.; Lukkari, J.; Pasanen, P.; Sillanpää, R.; Laine, H.; Harmaa, K.; Visy, C. Macromolecules 1994, 27, 4327-4334.
28. (b) Visy, C.; Lukkari, J.; Kankare, J. Macromolecules 1994, 27, 3322-3329.
29. (c) Sone, T.; Umetsu, Y.; Sato, K. Bull. Chem. Soc. Jpn. 1991, 64, 864-868.
30. (d) Sone, T.; Sato, K.; Umetsu, Y. Heterocydes 1984, 21, 596.
31. (e) Naudin, E.; Mehdi, N. E.; Soucy, C.; Breau, L.; Bélanger, D. Chem. Mater. 2001, 13, 634-642.
32. (a) Robitaille, L.; Leclerc, M. Chem. Mater. 1993, 5, 1755-1761.
33. (b) Guerrero, D.; Ren, X.; Ferraris, J. P. Chem. Mater. 1994, 6, 1437-1443.
34. (c) Ferraris, J. P.; Eissa, M. M.; Brotherston, I. D.; Loveday, D. C.; Moxey, A. A. J. Electroanal. Chem. 1998, 459, 57-69.
35. (d) Aasmundtveit, K. E.; Samuelsen, E. J.; Mammo, W.; Svensson, M.; Andersson, M. R.; Pettersson, L. A. A.; Inganäs, O. Macromolecules 2000, 33, 5481-5489.
36. (e) Andersson, M. R.; Selse, D.; Berggren, M.; Järvinen, H.; Hjertberg, T.; Inganäs, O.; Wennerström, O.; Österholm, J.-E. Macromolecules 1994, 27, 6503-6506.
37. (f) Ferraris, J. P.; Eissa, M. M.; Brotherston, I. D.; Loveday, D. C. Chem. Mater. 1998, 10, 3528-3535.
38. (g) Sato, M.; Tanaka, S.; Kaeriyama, K. Makromol. Chem. 1989, 190, 1233-1241.
39. (h) Chen, T.-A.; O'Brien, R. A.; Rieke, R. D. Macromolecules 1993, 26, 3462-3463.
40. (i) Ueda, M.; Miyaji, Y.; Ito, T.; Oba, Y.; Sone, T. Macromolecules 1991, 24, 2694-2697.
41. (j) Andersson, M. R.; Thomas, O.; Mammo, W.; Svensson, M.; Theander, M.; Inganäs, O. J. Mater. Chem. 1999, 9, 1933-1940.
42. (k) Andersson, M. R.; Berggren, M.; Inganäs, O.; Gustafsson, G.; Gustafsson-Carlberg, J. C.; Selse, D.; Hjertberg, T.; Wennerström, O. Macromolecules 1995, 28, 7525-7529.
43. (l) Andersson, M. R.; Mammo, W.; Olinga, T.; Svensson, M.; Theander, M.; Inganäs, O. Synth. Met. 1999, 101, 11-12.
44. (a) Sato, M. A.; Tanaka, S.; Kaeriyama, K. J. Chem. Soc., Chem. Commun. 1987, 1725-1726.
45. (b) Kaeriyama, K.; Tanaka, S.; Sato, M. A.; Hamada, K. Synth. Met. 1989, 28, C611-C620.
46. (c) Rudge, A.; Raistrick, I.; Gottesfeld, S.; Ferraris, J. P. Electrochim. Acta 1994, 39, 273-287.
47. (a) Sarker, H.; Gofer, Y.; Killian, J. G.; Poehler, T. O.; Searson, P. C. Synth. Met. 1997, 88, 179-185.
48. (b) Gofer, Y.; Killian, J. G.; Sarker, H.; Poehler, T. O.; Searson, P. C. J. Electroanal. Chem. 1998, 443, 103-115.
49. (c) Guerrero, D.; Ren, X.; Ferraris, J. P. Chem. Mater. 1994, 6, 1437-1443.
50. (d) Ferraris, J. P.; Eissa, M. M.; Brotherston, I. D.; Loveday, D. C.; Moxey, A. A. J. Electroanal. Chem. 1998, 459, 57-69.
51. (e) Ferraris, J. P.; Eissa, M. M.; Brotherston, I. D.; Loveday, D. C. Chem. Mater. 1998, 10, 3528-3535.
52. 11e
53. (a) Brummel, C. L.; Lee, I. N. W.; Zhou, Y.; Benkovic, S. J.; Winograd, N. Science 1994, 264, 399-402.
54. (b) Egner, B. J.; Langley, G. J.; Bradley, M. J. Org. Chem. 1995, 60, 2652-2653.
55. For problems of monitoring the reaction process, see ref 11e.
56. Kuisle, O.; Lolo, M.; Quinoa, E.; Riguera, R. Tetrahedron 1999, 55, 14807-14812.
57. Of serious concern was the trapping of gas bubbles within the microreactors under atmospheric pressure. When the reaction mixture was heated to reflux, microreactors floated on the solvent surface and the encapsulated resin shrunk considerably. The trapped gas bubbles restricted diffusion, which translated into poor yields (15% or less) for the cross-coupling reaction. It was beneficial at this point to conduct the reactions with the encapsulated resins in sealed heavy-walled round-bottom flasks to avoid the undesired trapping of gas bubbles inside the microreactor.
58. (a) Montheard, J.-P.; Delzant, J.-F.; Gazard, M. Synth. Commun. 1984, 14, 289-292.
59. (b) Wu, X.; Rieke, R. J. Org. Chem. 1995, 60, 6658-6659.
60. Srivastava, G. J. Indian Chem. Soc. 1962, 39, 203-207.
61. Coulson, D. R. Inorg. Synth. 1990, 28, 107-108.