Synthesis of end-blocked thienyl oligomers incorporating benzo[c]thiophene

Tetrahedron Letters

Volumn 48, Issue 5, 2007, Pages 779-784

  Mohanakrishnan, Arasambattu K ^a   Amaladass, P ^a   Arul Clement, J ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

Benzo c thiophene; Dimerization; Electronic properties; End capped thienyl oligomers

Indexed keywords

BENZO[C]THIOPHENE DERIVATIVE; OLIGOMER; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; CYCLIZATION; DIMERIZATION; ELECTROCHEMICAL ANALYSIS; FLUORESCENCE; OLIGOMERIZATION; QUALITATIVE ANALYSIS; SYNTHESIS;

EID: 33845914583     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.178     Document Type: Article

References (36)

1. Garnier F., Horowitz G., and Fichou D. Synth. Met. 28 (1989) 705-714
2. Garnier F., Horowitz G., Peng X., and Fichou D. Adv. Mater. 2 (1990) 592-594
3. Tour J.M. Acc. Chem. Res. 33 (2000) 791-804
4. Horowitz G., Delannoy P., Bouchriha H., Deloffre F., Fave J.L., Garnier F., Hajlaoui R., Heyman M., Kouki F., Valat P., Wintgens V., and Yassar A. Adv. Mater. 6 (1994) 752-755
5. Garnier F., Horowitz G., Peng X., and Fichou D. Adv. Mater. 2 (1990) 252
6. Xu B., Fichou D., Horowitz G., and Garnier F. Adv. Mater. 3 (1991) 150-153
7. Yoshino K. Synth Met. 28 (1989) 669-674
8. Knobloch H., Fichou D., Knoll W., and Sasabe H.. Adv. Mater. 5 (1993) 570-573
9. Fichou D., Nunzi J.-M., Charra F., and Pfeffer N. Adv. Mater. 6 (1994) 64-67
10. Hotta S., and Waragi K. J. Mater. Chem. 1 (1991) 835-842
11. Bredas J.L., Street G.B., Themans B., and Andre J.-M. J. Chem. Phys. 83 (1985) 1323-1329
12. Tour J.M., Wu R., and Schumm J.S. J. Am. Chem. Soc. 113 (1991) 706-707
13. Tour J.M., and Wu R. Macromolecules 25 (1992) 1901-1907
14. Bauerle P. Adv. Mater. 4 (1992) 102-107
15. Parakka J., and Cava M.P. Tetrahedron 51 (1995) 2229-2242
16. Zotti G., Schiavon G., Berlin A., and Pagani G. Synth. Met. 61 (1993) 81-87
17. Hotta S., and Waragai K. Adv. Mater. 5 (1993) 896-908
18. Garnier F., Yassar A., Hajlaoui R., Horowitz G., Deloffre F., Servet B., Ries S., and Alnot P. J. Am. Chem. Soc. 115 (1993) 8716-8721
19. Garnier F., Hajlaoui R., Yassar A., and Srivastava P. Science 265 (1994) 1684-1686
20. Lorcy D., and Cava M.P. Adv. Mater. 4 (1992) 562-564
21. Bauerle P., Gotz G., Emerle P., and Port H. Adv. Mater. 4 (1992) 564-568
22. Musinanni S., and Ferraris J.P. J. Chem. Soc., Chem. Commun. (1993) 172-174
23. Kiebooms R.H.L., Adriaensens P.J.A., Vanderzande D.J.N., and Gelan J.M.J.V. J. Org. Chem. 62 (1997) 1473-1480
24. Mohanakrishnan A.K., Lakshmikantham M.V., McDougal C.D., Cava M.P., Baldwin J.W., and Metzger R.M. J. Org. Chem. 63 (1998) 3105-3112
25. Raimundo J.M., Blanchard P., Brisset H., Akoudad S., and Roncali J. Chem. Commun. (2000) 939-940
26. Strassler C., Davis N.E., and Kool E.T. Helv. Chim. Acta 82 (1999) 2160-2171
27. Mohanakrishnan A.K., and Amaladass P. Tetrahedron Lett. 46 (2005) 4225-4229
28. The required 5-substituted thienylmagnesium bromides 6 were prepared as mentioned below:{A figure is presented}
29. Bäuerle P., Fischer T., Bidlingmeir B., Stable A., and Rabe J.P. Angew. Chem., Int. Ed. Engl. 34 (1995) 303-307
30. Groenendaal L.B., Jonas F., Freitag D., Pielartzik H., and Reynolds J.R. Adv. Mater. 12 (2000) 481-494
31. Barbarella G., Zambianchi M., Di Toro R., Colonna Jr. M., Iarossi D., Goldoni F., and Bongini A. J. Org. Chem. 61 (1996) 8285-8292
32. Mustafa A.H., and Shepherd M.K. Chem. Commun. (1998) 2743-2744
33. Thoma H., Iwata M., Maegawa T., Kiyono Y., Maruyama A., and Kita Y. Org. Biomol. Chem. 1 (2003) 1647-1649
34. 4: C, 67.20; H, 5.21; S, 27.60. Found: C, 67.08; H, 5.25; S, 27.62.
35. 4: C, 77.38; H, 3.84; S, 18.78. Found: C, 77.51; H, 3.80; S, 18.69.
36. 2: C 80.68; H, 4.96; S, 14.36. Found: C, 80.79; H, 4.91; S, 14.30.