Stepwise unidirectional synthesis of oligo phenylene vinylenes with a series of monomers. Use in plastic solar cells

Journal of Organic Chemistry

Volumn 70, Issue 15, 2005, Pages 6004-6017

  Jørgensen, Mikkel ^a   Krebs, Frederik C ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; COMPOSITION; ESTERS; MONOMERS; PHENOLIC RESINS; PHOSPHORIC ACID; PHOTOVOLTAIC CELLS; SOLAR CELLS; SOLUBILITY; SYNTHESIS (CHEMICAL);

DIETHYL ESTER; HETROTRIMERS; OLIGOPHENYLENEVINYLENES (OPV); TERPYRIDINES;

OLIGOMERS;

[4 [2 [4 (5,5 DIMETHYL[1,3]DIOXAN 2 YL) 2,5 DIPROPOXYPHENYL]VINYL]BENZYL]PHOSPHONIC ACID DIETHYL ESTER; [5 [2 [4 (5,5 DIMETHYL[1,3]DIOXAN 2 YL) 2,5 DIPROPOXYPHENYL]VINYL]THIOPHEN 2 YLMETHYL]PHOSPHONIC ACID DIETHYL ESTER; [5 [2 [4 (5,5 DIMETHYL[1,3]DIOXAN 2 YL) 2,5 DIPROPYLPHENYL]VINYL]THIOPHEN 2 YLMETHYL]PHOSPHONIC ACID DIETHYL ESTER; [7 [2 [4 (5,5 DIMETHYL[1,3]DIOXAN 2 YL) 2,5 DIPROPYLPHENYL]VINYL]BENZO[1,2,5]THIADIAZOL 4 YLMETHYL]PHOSPHONIC ACID DIETHYL ESTER; MONOMER; OLIGOPHENYLENEVINYLENE DERIVATIVE; THIADIAZOLE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; LIGHT ABSORPTION; POLYMERIZATION; SYNTHESIS;

EID: 22244436883     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0506783     Document Type: Article

References (46)

1. (a) Müllen, K.; Wegner, G. Electronic Materials: The Oligomer Approach; Wiley-VCH: Weinheim, 1998.
2. (b) Wong, M. S.; Li, Z. H. Pure Appl. Chem. 2004, 76, 1409-1419.
3. Granström, M.; Petritsch, K.; Arias, A. C.; Lux, A.; Anderson, M. R.; Friend, R. H. Nature 1998, 395, 257-260.
4. Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C. Adv. Funct. Mater. 2001, 11, 15-26.
5. Spangaard, H.; Krebs, F. C. Sol. En. Mater. Sol. Cells 2004, 83, 125-146.
6. Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H. Science 2001, 293, 1119-1122.
7. Meier, H.; Gerold, J.; Kolshorn, H.; Muling, B. Chem. Eur. J. 2004, 10, 360-370.
8. Jørgensen, M.; Krebs, F. C. J. Org. Chem. 2004, 69, 6688-6696.
9. (a) Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402-428.
10. (b) Yang, J. P.; Heremens, P. L.; Haefnagels, R.; Tachelet, W.; Dielteens, P.; Blockhuys, F.; Giese, H. J.; Borghs, G. Synth. Met. 2000, 108, 95-100.
11. (c) Meier, H.; Gerold, J.; Kolshorn, H.; Baumann, W.; Bletz, M. Angew. Chem., Int. Ed. 2002, 41, 292-295.
12. Detert, H.; Stalmach, U. J. Prakt. Chem. 2000, 342, 10-16.
13. Van Hutten, P. F.; Wildeman, J.; Meetsma, A.; Hadziioannou, G. J. Am. Chem. Soc. 1999, 121, 5910-5918.
14. Babudri, F.; Farinola, G. M.; Lopez, L. C.; Martinelli, M. G.; Naso, F. J. Org. Chem. 2001, 66, 3878-3885.
15. (a) Li, W.; Wang, H.; Yu, L.; Morkved, T. L.; Jaeger, H. M. Macromolecules 1999, 32, 3034-3044.
16. (b) Maddux, T.; Li, W.; Yu, L. J. Am. Chem. Soc. 1997, 119, 844-845.
17. Nierengarten, J.-F.; Eckert, J.-F.; Felder, D.; Nicoud, J.-F.; Armaroli, N.; Marconi, G.; Vicinelli, V.; Boudon, C.; Gisselbrecht, J.-P.; Gross, M.; Hadziioannou, G.; Karsnikov, V.; Ouali, L.; Echegoyen, L.; Liu, S.-G. Carbon 2000, 38, 1587-1598.
18. Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989-7000.
19. Meier, H.; Aust, H. J. Prakt. Chem. 1999 341, 466-471.
20. Xue, C.; Luo, F.-T. Tetrahedron 2003, 59, 5193-5198.
21. (a) Masatome, I.; Milton, L. L.; Castle, R. J. Heterocycl. Chem. 1980, 17, 1259-1264.
22. (b) Berlin, A.; Bradamante, S.; Ferraccioli, R.; Pagani, G. A.; Sannicolo, F. J. Chem. Soc., Perkin Trans, 1 1987, 2631-2636.
23. Wang, C.; Dalton, L. R. Tetrahedron Lett. 2000, 41, 617-620.
24. Frère, P.; Raimundo, J.-M.; Blanchard, P.; Delaunay, J.; Richomme, P.; Sauvajol, J.-L.; Orduna, J.; Roncali, J. J. Org. Chem. 2003, 68, 7254-7265.
25. Michaelis, A. Ann. Chem. 1893, 273, 173-268 (p 263).
26. Pilgram, K.; Zupan, M.; Skiles, R. J. Heterocycl. Chem. 1970, 7, 629-633.
27. Vanelle, P.; Liegois, C. T.; Meuche, J.; Maldonado, J.; Crozet, M. P. Heterocycles 1997, 45, 955-962.
28. Liu, Y.; Prashad, M.; Repiè, O.; Blacklock, T. J. J. Heterocycl. Chem. 2003, 40, 713-716.
29. Leusink, A. J.; Budding, H. A.; Marsman, J. W. J. Organomet. Chem. 1967, 9, 285-294.
30. Leusink, A. J.; Budding, H. A. J. Organomet. Chem. 1967, 11, 533-539.
31. Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881-884.
32. Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 778, 2748-2749.
33. Kang, S.-K.; Kim, J.-S.; Yoon, S.-K.; Lim, K.-H.; Yoon, S.-S. Tetrahedron Lett. 1998, 39, 3011-3012.
34. Roth, G. P.; Farina, V.; Liebeskind, L. S.; Peña-Cabrera, E. Tetrahedron Lett. 1995, 36, 2191-2194.
35. Shirakawa, E.; Yamasaki, K.; Hiyama, T. Synthesis 1998, 10, 1544-1549.
36. Kang, S.-K.; Kim, J.-S.; Choi, S.-C. J. Org. Chem. 1997, 62, 4208-4209.
37. El-ghayoury, A.; Schenning, A. P. H. J.; van Hal, P. A.; Weidl, C. H.; van Dongen, J. L. J.; Janssen, R. A. J.; Schubert, U. S.; Meijer, E. W. Thin Solid Films 2002, 403-404, 97-101.
38. Zhang, Y.; Murphy, C. B.; Jones, W. E., Jr. Macromolecules 2002, 35, 630-636.
39. Collin, J.-P.; Guillerez, S.; Sauvage, J.-P.; Barigelletti, F.; De Cola, L.; Flamigni, L.; Balzani, V. Inorg. Chem. 1991, 30, 4230-4238.
40. Spahni, W.; Calzaferri, G. Helv. Chim. Acta 1984, 67, 450.
41. Krebs, F. C.; Jørgensen, M. Macromolecules 2003, 36, 4374-4384.
42. Hummelen, J. C.; Knight, B. W.; LePeq, F.; Wudl, F.; Yao, J.; Wilkins, C. L. J. Org. Chem. 1995, 60, 532-538.
43. Cave, G. W. V.; Raston, C. L. J. Chem. Soc., Perkin Trans, 1 2001, 3258-3264.
44. Krebs, F. C.; Jørgensen, M. Rev Sci. Instrumen. 2003, 74, 3438-3442.
45. Krebs, F. C.; Carlé, J. E.; Cruys-Bagger, N.; Andersen, M.; Lilliedal, M. R.; Hammond, M. A.; Hvidt, S. Sol. En. Mater. Sol. Cells 2005, 86, 499-516.
46. Norrman, K.; Krebs, F. C. Sol. En. Mater. Sol. Cells 2005, web release April 18, 2005.