Oligothiophene S,S-Dioxides. Synthesis and Electronic Properties in Relation to the Parent Oligothiophenes

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5497-5506

  Barbarella, G ^a   Favaretto, L ^a   Sotgiu, G ^a   Zambianchi, M ^a   Antolini, L ^b   Pudova, O ^c   Bongini, A ^d  

^a CNR   (Italy)

^b UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^c LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

^d UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000255786     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980507g     Document Type: Article

References (42)

1. (a) Vorontsova, L. G. J. Struct. Chem. 1966, 7, 234.
2. (b) Gronowitz, S. Phosphorus, Sulfur Silicon 1993, 74, 113.
3. (c) Gronowitz, S.; Hörnfeldt, A. B.; Lukevics, E.; Pudova, O. Synthesis 1994, 40.
4. (d) Furukawa, N.; Hoshiai, H.; Shibutani, T.; Higaki, M.; Iwasaki, F.; Fujihara, H. Heterocycles 1992, 34, 1085.
5. (e) O'Donovan, A. R. M.; Shepherd, M. K. Tetrahedron Lett. 1994, 35, 4425.
6. (f) Miyahara, Y.; Inazu, T. Tetrahedron Lett. 1990, 31, 5955.
7. Rozen, S.; Bareket, Y. J. Org. Chem. 1997, 62, 1457.
8. Nakayama, J.; Nagasawa, H.; Sugihara, Y.; Ishii, A. J. Am. Chem. Soc. 1997, 119, 9077.
9. (a) Barbarella, G.; Pudova, O.; Arbizzani, C.; Mastragostino, M.; Bongini, A. J. Org. Chem. 1998, 63, 1742.
10. (b) Barbarella, G.; Favaretto, L.; Zambianchi, M.; Pudova, O.; Arbizzani, C.; Bongini, A.; Mastragostino, M. Adv. Mater. 1998, 10, 551.
11. (c) Barbarella, G.; Zambianchi, M.; Sotgiu, G.; Bongini, A. Tetrahedron 1997, 53, 9401.
12. (d) Barbarella, G.; Zambianchi, M.; del Fresno, M.; Marimon, I.; Antolini, L.; Bongini, A. Adv. Mater. 1997, 9, 484.
13. (a) Hajlaoui, R.; Horowitz, G.; Garnier, F.; Arce-Brouchet, A.; Laigre, L.; El Kassmi, A.; Demanze, F.; Kouki, F. Adv. Mater. 1997, 9, 389.
14. (b) Garnier, F.; Hajlaoui, R.; Yassar, A.; Srivastava, P. Science 1994, 265, 1684.
15. (c) Dodabalapur, A.; Torsi, L.; Katz, H. E. Science 1995, 268, 270.
16. (d) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595.
17. (e) Fichou, D.; Nunzi, J. M.; Charra, F.; Pfeffer, N. Adv. Mater. 1994, 6, 64.
18. (f) Arbizzani, C.; Bongini, A.; Mastragostino, M.; Zanelli, A.; Barbarella, G.; Zambianchi, M. Adv. Mater. 1995, 7, 571.
19. (g) Geiger, F.; Stoldt, M.; Schweitzer, H.; Bäuerle, P.; Umbach, E. Adv. Mater. 1993, 5, 922.
20. (h) Tsivgoulis, G. M.; Lehn, J. M. Adv. Mater. 1997, 9, 39.
21. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
22. (a) Yassar, A.; Garnier, F.; Deloffre, F.; Horowitz, G.; Ricard, L. Adv. Mater. 1994, 6, 660.
23. (b) Garnier, F.; Yassar, A.; Hajlaoui, R.; Horowitz, G.; Deloffre, F.; Servet, B.; Ries, S.; Alnot, P. J. Am. Chem. Soc. 1993, 15, 8716.
24. Higuchi, H.; Nakayama, T.; Koyama, H.; Ojima, J.; Wada, T.; Sasabe, H. Bull. Chem. Soc. Jpn. 1995, 68, 2363.
25. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
26. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, J.; Guy Orpen, A.; Taylor, R. J. Chem. Soc. Perkin Trans. 2 1987, S1-S19.
27. Gaussian 94, Revision E.2: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
28. (a) Jursic, B. S. J. Heterocyclic Chem. 1995, 32, 1445.
29. (b) Rozas, I. J. Phys. Org. Chem. 1992, 5, 74.
30. (a) Samdal, S.; Samuelsen, E. J.; Volden, H. V. Synth. Met. 1993, 59, 259.
31. (b) Ortí, E.; Viruela, P. M.; Sanchez-Marin, J.; Tomes, F. J. Phys. Chem. 1995, 99, 4955.
32. (c) Hernandez, V.; Lopez Navarrete, J. T. J. Chem. Phys. 1994, 101, 1373.
33. (a) Farina, V. J. Am. Chem. Soc. 1991, 113, 9585.
34. (b) Farina, V.; Roth, G. P. Tetrahedron Lett. 1991, 32, 4243.
35. (c) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
36. (d) Roth, G. P.; Farina, V.; Liebeskind, L. S.; Peña-Cabrera, E. Tetrahedron Lett. 1995, 36, 2191.
37. De Leew, D. M.; Simenon, M. M. J.; Brown, A. R.; Einerhand, R. E. F. Synth. Met. 1997, 87, 53-59.
38. Caronna, T.; Forte, M.; Catellani, M.; Meille, S. V. Chem. Mater. 1997, 9, 991.
39. McCullogh, R. D. Adv. Mater. 1998, 10, 93.
40. Roncali, J. Chem. Rev. 1997, 97, 173.
41. Miller, L. L.; Yu, Y. J. Org. Chem. 1995, 60, 6813.
42. Van Pham, C.; Burkhardt, A.; Nkansah, A.; Shabana, R.; Cunnigham, D. D.; Mark, H. B., Jr.; Zimmer, H. Phosphorus, Sulfur, Silicon Relat. Elem. 1989, 46, 153.