Polyhydroxyoligothiophenes. 2. Hydrogen-bonding-oriented solid state conformation of 3,3′-bis(2-hydroxyethyl)-2,2′-bithiophene and regioselective synthesis of the corresponding head-to-head/tail-to-tail quater-and sexithiophene

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4708-4715

  Barbarella, G ^a   Zambianchi, M ^a   Bongini, A ^b   Antolini, L ^c  

^a CNR   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000095292     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952278t     Document Type: Article

References (46)

1. (a) Roncali, J. Chem. Rev. 1992, 92, 711.
2. (b) Garnier, F. Angew. Chem., Int. Ed. Engl. 1989, 28, 513.
3. (c) Bäuerle, P. Adv. Mater. 1993, 5, 879.
4. (d) Marsella M. J.; Newland, R. J.; Carrol, P. J.; Swager, T. M. J. Am. Chem. Soc. 1995, 117, 9842.
5. (e) Marsella, M. J.; Carrol, P. J.; Swager, T. M. J. Am. Chem. Soc. 1995, 117, 9832.
6. (a) Patil, A. O.; Ikenoue, Y.; Wudl, F.; Heeger, A. J. J. Am. Chem. Soc. 1987, 109, 1858.
7. (b) Ikenoue, Y.; Chiang, J.; Patil, A. O.; Wudl, F.; Heeger, A. J. J. Am. Chem. Soc. 1988, 110, 2983.
8. (c) Bäuerle, P.; Gaudl, K. U.; Würthner, F.; Sarifitci, N. S.; Neugebauer, H.; Mehring, M.; Zhong, C.; Doblhofer, K. Adv. Mater. 1990, 2, 490.
9. (d) APE Associates S.A., Bruxelles, European Patent Application no. 09300449.
10. (a) McCullough, R. D.; Williams, S. P. J. Am. Chem. Soc. 1993, 115, 11608.
11. (b) McCullough, R. D.; Lowe, R D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904.
12. (b) Chen, T.; Wu, X.; Riecke, R. D. J. Am. Chem. Soc. 1995, 117, 233.
13. (c) Iraqi, A.; Crayston, G. A.; Walton, J. C. J. Mater. Chem. 1995, 5, 1831.
14. Garnier, F.; Yassar, A.; Hailaoui, R.; Horowitz, G.; Deloffre, F.; Servet, B.; Ries, S.; Alnot, P. J. Am. Chem. Soc. 1993, 115, 8716.
15. (a) Dodabalapur, A.; Torsi, L.; Katz, H. E. Science 1995, 268, 270.
16. (b) Dodabalapur, A.; Katz, H. E.; Torsi, L.; Haddon, R. C. Science 1995, 269, 1560.
17. Barbarella, G.; Zambianchi, M. Tetrahedron 1994, 50, 11249.
18. Hanessian, S.; Gomtsyan, A.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1994, 116, 4495.
19. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
20. (b) Farina, V. J. Am. Chem. Soc. 1991, 113, 9585.
21. (c) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
22. Visser, G. J.; Heeres G. J.; Wolters, J.; Vos, A. Acta Crystallogr. 1968, B24, 467.
23. Pyrka, G. J.; Fernando, Q.; Inoue, M. B.; Inoue, M.; Velazquez, F. Acta Crystallogr. 1988, C44, 562.
24. Paulus, E. F.; Dammel, R.; Kämpf, G.; Wegener, P.; Siam, K.; Wolinski, K.; Schäfer, L. Acta Crystallogr. 1988, B44, 509.
25. (a) Barbarella, G.; Zambianchi, M.; Antolini, L.; Folli, U.; Goldoni, F.; Iarossi, D.; Schenetti, L. J. Chem. Soc., Perkin Trans. 2 1995, 1869.
26. (b) Barbarella, G.; Zambianchi, M.; Antolini, L.; Bongini, A. Adv. Mater. 1994, 6, 561.
27. (c) Adv. Mater. 1992, 4, 282.
28. (c) Adv. Mater. 1993, 5, 834.
29. Van Bolhuis, F.; Wynberg, H.; Havinga, E. E.; Meijer, E. W.; Staring, E. G. J. Synth. Met. 1989, 30, 381.
30. Hotta, S., Waragai, K. J. Mater. Chem. 1991, 1, 835.
31. Yassar, A.; Garnier, F.; Deloffre, F.; Horowitz, G.; Ricard, L. Adv. Mater. 1994, 6, 660.
32. Liao, J. H; Benz, M.; LeGoff, E.; Kanatzdis, M. G. Adv. Mater. 1994, 6, 135.
33. Herrema, J. K; Wildeman, J; Van Bolhuis, F.; Hadziioannou, G. Synth. Met. 1993, 60, 239.
34. Meille, S. V.; Farina, A.; Bezziccheri, F.; Gallazzi, M. C. Adv. Mater. 1994, 6, 848.
35. Bäuerle, P; Würthner, F.; Götz, G.; Effenberger, F. Synthesis 1993, 1099.
36. Barbarella, G.; Bongini, A.; Zambianchi, M. Tetrahedron 1992, 48, 6701.
37. Horowitz, G.; Bachet, B.; Yassar, A.; Lang, P.; Demanze, F.; Fave, J. L.; Garnier, F. Chem. Mater. 1995, 7, 1337.
38. Barbarella, G.; Bongini, A.; Zambianchi, M. Macromolecules 1994, 27, 3039.
39. Allinger, N. L.; Yuh, Y. H.; Lii, J. H. J. Am. Chem. Soc. 1989, 111, 8551.
40. Samdal, S.; Samuelsen, E. J.; Valden, H. Synth. Met. 1993, 59, 259.
41. Quantum Chemistry Program Exchange, University of Indiana, Bloomington, IN 47405.
42. (a) Tamao, K.; Kodama, S.; Nakajima, I; Kumada, M. Tetrahedron 1982, 38, 3347.
43. (b) Van Pham, C.; Burkhardt, A.; Shabana, R.; Cunnigham, D. D.; Mark, H. B., Jr.; Zimmer, H. Phosphorus, Sulfur Silicon 1989, 46, 153.
44. Bredas, J. L.; Street G. B., Thémans, B.; André, J. M. J. Chem. Phys. 1985, 83, 1323.
45. Gavezzotti, A.; Filippini, G. Synth. Met. 1991, 40, 257.
46. The author has 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.