Cyano-substituted oligothiophenes: A new approach to n-type organic semiconductors

Advanced Functional Materials

Volumn 12, Issue 10, 2002, Pages 699-708

  Yassar, A ^a   Demanze, F ^a   Jaafari, A ^b   El Idrissi, M ^b   Coupry, C ^c  

^a ITODYS1 ^*  (France)

^b Laboratoire de Chimie Organique   (Morocco)

^c Centre National de la Recherche Scientifique Université Pierre et Marie Curie Paris 6 Sorbonne Universités   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL VAPOR DEPOSITION; CURRENT VOLTAGE CHARACTERISTICS; ELECTROCHEMISTRY; FUNCTIONALLY GRADED MATERIALS; MOLECULAR DYNAMICS; PALLADIUM; SEMICONDUCTING ORGANIC COMPOUNDS; STACKING FAULTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

BATHOCHROMIC SHIFT; CYANO-SUBSTITUTED OLIGOTHIOPHENES; ELECTRON AFFINITY; INTERMOLECULAR CONTACTS; PALLADIUM CATALYZED COUPLING REACTION; STILLE COUPLING REACTION;

OLIGOMERS;

EID: 0036809398     PISSN: 1616301X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1616-3028(20021016)12:10<699::AID-ADFM699>3.0.CO;2-S     Document Type: Article

References (51)

1. (a) H. E. Katz, J. Mater. Chem. 1997, 7, 369.
2. (b) F. Garnier, A. Yassar, R. Hajlaoui, G. Horowitz, F. Delloffre, B. Servet, S. Ries, P. Alnot, J. Am. Chem. Soc. 1993, 115, 8716.
3. (c) J. G. Laquindanum, H. E. Katz, J. A. Lovinger, J. Am. Chem. Soc. 1998, 120, 664.
4. (a) G. Horowitz, F. Garnier, A. Yassar, R. Hajlaoui, F. Kouki, Adv. Mater. 1996, 6, 52.
5. (b) J. H. Schön, C. Kloc, R. A. Laudisie, B. Batlogg, Appl. Phys. Lett. 1998, 73, 3574.
6. (a) N. C. Greenham, S. C. Moratti, D. D. C. Bradley, R. H. Friend, A. B. Homes, Nature 1993, 365, 628.
7. (b) A. R. Brown, D. M. Leeuw, E. J. Lous, E. E. Havinga, Synth. Met. 1994, 66, 257.
8. (a) G. Barbarella, O. Pudova, C. Arbizzani, M. Mastragostino, A. Bongini, J. Org. Chem. 1998, 63, 1742.
9. (b) K. Amao, M. Uchida, T. Izumizawa, K. Furakawa, S. Yamaguchi, J. Am. Chem. Soc. 1996, 118, 11974.
10. (c) A. Donat-Bouillud, L. Mazerolle, P. Gagnon, L. Goldenberg, M. C. Petty, M. Leclerc, Chem. Mater. 1997, 9, 2815.
11. (d) H. A. Ho, H. Brisset, E. Elandaloussi, P. Frère, J. Roncali, Adv. Mater. 1996, 8, 990.
12. (a) C. Adachi, T. Tsutsui, S. Saito, Appl. Phys. Lett. 1992, 61, 2793.
13. (b) B. Brown, D. D. C. Bradley, J. H. Burroughs, R. H. Friend, N. C. Greenham, P. L. Burn, A. B. Holmes, A. Kraft, Appl. Phys. Lett. 1992, 61, 2793.
14. M. Strukelj, F. Papadimitrakopoulos, T. M. Miller, L. J. Rothberg, E. A. Chandross, Science 1995, 267, 1969.
15. M. S. Weaver, D. O'Brien, A. Bleyer, D. G. Lidzey, D. D. C. Bradley, in Organic and Inorganic Electroluminescence (Eds: R. H. Mauch, H. E. Gumlich), Wissenschaft & Technik Verlag, Berlin 1996.
16. T. M. Barclay, A. W. Cordes, C. D. Mackinnon, R. T. Oakley, R. W. Reed, Chem. Mater. 1997, 9, 981.
17. (a) J. Kagan, S. K. Arora, A. Ustünol, J. Org. Chem. 1983, 48, 4076.
18. (b) A. MacEachern, C. Soucy, L. C. Leitch, J. T. Arnasson, P. Morand, Tetrahedron 1988, 44, 2403.
19. (c) P. Garcia, J. M. Pernaut, P. Hapiot, V. Wintgens, P. Valat, F. Garnier, D. Delabouglise, J. Phys. Chem. 1993, 97, 513.
20. (d) J. Nakayama, S. Murabayashi, M. Hoshino, Heterocycles 1986, 24, 2639.
21. L. Fridman, H. Shechter, J. Org. Chem. 1961, 26, 2522.
22. C. Soucy-Breau, A. MacEachern, L. C. Leitch, T. Arnasson, P. Morand, J. Heterocyclic Chem. 1991, 28, 411.
23. J. M. Barker, P. R. Huddleston, in Thiophene and Its Derivatives, Part 3 (Ed: S. Gronowitz), John Wiley and Sons, New York 1986.
24. S. Gronowitz, S. Liljeforts, Acta Chem. Scand. 1977, B31, 771.
25. R. Rossi, A. Caprita, C. Maurizio, P. Lippolis, Tetrahedron 1991, 47, 8443.
26. (a) P. Cagniant, D. Cagniant, D. Paquer, G. Kirsch, in Thiophene and Its Derivatives, Part 2 (Ed: S. Gronowitz), John Wiley and Sons, New York 1986.
27. (b) O. Exner, M. Budesinsky, Magn. Reson. Chem. 1989, 27, 27.
28. (a) F. Van Bolhuis, H. Wijnberg, E. E. Havinga, W. E. Meijer, E. G. J. Staring, Synth. Met. 1989, 30, 381.
29. (b) S. Hotta, K. Waragai, J. Mater. Chem. 1991, 1, 835.
30. (c) G. Horowitz, B. Bachet, A. Yassar, P. Lang, F. Demanze, J.-L. Fave, F. Garnier, Chem. Mater. 1995, 7, 1337.
31. (d) D. Fichou, B. Bachet, F. Demanze, I. Billy, G. Horowitz, F. Garnier, Adv. Mater. 1996, 8, 500.
32. (b) H.-J. Egelhaaf, P. Bäuerle, K. Rauer, V. Hoffmann, D. Oelkrug, Synth. Met. 1993, 61, 143.
33. (c) A. Yassar, G. Horowitz, P. Valat, V. Wintgens, M. Hmyene, F. Deloffre, P. Lang, F. Garnier, J. Phys. Chem. 1995, 99, 9155.
34. M. Pope, C. E. Swenberg, Electronic Processes in Organic Crystals, Oxford University Press, New York 1982.
35. (a) V. Bulovic, P. E. Burrows, S. R. Forrest, J. A. Cronin, M. E. Thompson, Chem. Phys. 1996, 210, 1.
36. (b) M. K. Kelly, P. Etchegoin, D. Fuchs, W. Kratschmer, K. Fostiropoulos, Phys. Rev. B 1992, 46, 4963.
37. (c) J. Tanaka, Bull. Chem. Soc. Jpn. 1963, 36, 1237.
38. (d) S. R. Forrest, Chem. Rev. 1997, 97, 179.
39. (a) R. C. Haddon, A. S. Perel, R. C. Morris, T. T. M. Palstra, A. F. Hebard, R. M. Fleming, Appl. Phys. Lett. 1995, 67, 121.
40. (b) R. C. Haddon, J. Am. Chem. Soc. 1996, 118, 3041.
41. (c) J. G. Laquindanum, H. E. Katz, A. J. Lovinger, J. Am. Chem. Soc. 1996, 118, 11 331.
42. J. H. Schön, C. Kloc, B. Batlogg, Org. Electron. 2000, 1, 57.
43. S. M. Sze, Physics of Semiconductor Devices, 2nd ed., John Wiley and Sons, New York 1981.
44. C. Väterlein, H. Neureiter, W. Gebauer, B. Ziegler, M. Sokolowski, P. Bäuerle, E. Umbach, J. Appl. Phys. 1997, 82, 3003.
45. W. R. Salaneck, S. Stafström, J.-L. Brédas, Conjugated Polymer Surfaces and Interfaces, Cambridge University Press, New York 1996.
46. A. J. Loving, Z. Bao, A. Dodabalapur, H. E. Katz, A. J. Laquindanum, Polym. Prepr. 1998, 39, 92.
47. J. R. Ostick, A. Dodabalapur, L. Torsi, A. J. Lovinger, E. W. Kwock, T. M. Miller, M. Galvin, M. Berggren, H. E. Ka J. Appl. Phys. 1997, 81, 6804.
48. P. Bäurle, F. Würthner, G. Götz, F. Effenberger, Synthesis 1993, 1099.
49. G. F. Pedulli, M. Tiecco, M. Guerra, G. Martelli, P. J. Zanirato, J. Chem. Soc. Perkin Trans. 2 1978, 212
50. Y. Wei, Y. Yang, J.-M. Yeh, Chem. Mater. 1996, 8, 2659.
51. G. A. Sotzing, J. R. Reynolds, P. J. Steel, Chem. Mater. 1996, 8, 882.