6-(Arylvinylene)-3-pyridinylboronic esters. Part 1: Versatile building blocks for conjugated chromophores via Suzuki cross-coupling

Tetrahedron Letters

Volumn 44, Issue 31, 2003, Pages 5879-5882

  Leclerc, Nicolas ^a   Serieys, Isabelle ^a   Attias, André Jean ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

6 (4 ETHANOL 2 THIENYLVINYLENE) 5 METHYL 3 BROMOPYRIDINE; 6 (4 HEXYL 2 THIENYLVINYLENE) 5 METHYL 3 BROMOPYRIDINE; BIPYRIDINE DERIVATIVE; BROMINE DERIVATIVE; ESTER DERIVATIVE; HYDROXYL GROUP; PALLADIUM; TRANSITION ELEMENT; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOPHORE; CONJUGATION; POLYMERIZATION; STRUCTURE ANALYSIS; SUZUKI REACTION; SYNTHESIS;

LATEOLABRAX JAPONICUS;

EID: 0038639663     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01393-5     Document Type: Article

References (33)

1. Burroughes J.H., Bradley D.D.C., Brown A.R., Marks R.N., Mackay K., Friend R.H., Burns P.L., Holmes A.B. Nature. 347:1990;539-541.
2. Kraf A., Grimsdale A.C., Holmes A.B. Angew. Chem., Int. Ed. 37:1998;402-428.
3. Nalwa H.S., Miyata S. Nonlinear Optics of Organic Molecules and Polymers. 1997;CRC Press, Boca Raton, FL.
4. Gubler U., Bosshard C. Adv. Polym. Sci. 158:2001;123-191.
5. Sariciftci N.S., Smilowitz L., Heeger A.J., Wudl F. Science. 258:1992;1474-1476.
6. Halls J.J.M., Walsh C.A., Greenham N.C., Marseglia E.A., Friend R.H., Moratti S.C., Holmes A.B. Nature. 376:1995;498-500.
7. Brabec C.J., Sariciftci N.S., Hummelen J.C. Adv. Funct. Mater. 11:2001;15-26.
8. Baigent D.R., Friend R.H., Lee J.K., Schrock R.R. Synth. Met. 71:(1-3):1995;2171-2172.
9. Boyd T.J., Geerts Y., Lee J.-K., Fogg D.E., Lavoie G.G., Schrock R.R., Rubner M.F. Macromol. 30:1997;3553-3559.
10. Bao Z., Peng Z., Galvin M.E., Chandross E.A. Chem. Mater. 10:(5):1998;1201-1204.
11. Bouché C.M., Berdagué P., Facoetti H., Robin P., Le Barny P., Schott M. Synth. Met. 81:1996;191-195.
12. Dalton L. Adv. Polym. Sci. 158:2001;1-121.
13. Attias A.-J., Cavalli C., Bloch B., Guillou N., Noël C. Chem. Mater. 11:1999;2057-2068.
14. Attias A.-J., Hapiot P., Wintgens V., Valat P. Chem. Mater. 12:2000;461-471.
15. Lemaître N., Attias A.-J., Ledoux I., Zyss J. Chem. Mater. 13:2001;1420-1427.
16. Chérioux F., Attias A.-J., Maillotte H. Adv. Funct. Mater. 12:2002;203-208.
17. Henze O., Lehman U., Schlüter A.D. Synthesis. 4:1999;683-687.
18. Henze O., Lentz D., Schlüter A.D. Chem. Eur. J. 6:2000;2362-2367.
19. Henze O., Lentz D., Schäfer A., Franke P., Schlüter A.D. Chem. Eur. J. 8:2002;357-365.
20. Schubert U.S., Eschbaumer C., Heller C. Org. Lett. 2:2000;3373-3376.
21. Fuller A.A., Hester H.R., Salo E.V., Stevens E.P. Tetrahedron Lett. 44:2003;2935-2938.
22. Constable E.C., Morris D., Carr S. New J. Chem. 22:1998;287-291 references herein.
23. Ishikura M., Kamada M., Terashima M. Synthesis. 1984;936-938.
24. Gronowitz S., Björk P., Malm J., Hörnfeld A.-B. J. Org. Chem. 460:1993;127-129.
25. Bouillon A., Lancelot J.C., Collot V., Bovy P.R., Rault S. Tetrahedron. 58:2002;3323-3328.
26. Lopez S., Kahraman M., Harmata M., Keller S.W. Inorg. Chem. 36:1997;6138-6140.
27. Radig R.S., Lam R., Zavalij O.Y., Katala Ngala J., LaDuca R.L., Greedam J.E., Zubieta J. Inorg. Chem. 41:2002;2124-2133.
28. Linda P., Marino G., Santini S. Tetrahedron Lett. 11:1970;4223-4224.
29. Juris A., Campagna S., Bidd I., Lehn J.-M., Ziessel R. Inorg. Chem. 27:1988;4007-4011.
30. Maury O., Guégan J.-P., Renouard T., Hilton A., Dupau P., Sandon N., Toupet L., Le Bozec H. New J. Chem. 25:2001;1553-1566.
31. 4. The solvent was removed under reduced pressure. The crude product was purified by filtration on silica (chlorform-ethyl acetat 9:1) yielding pure compound B( 1 ) (9.97 g, 20.5 mmol) in a 91% yield as yellowish oil.
32. 4. The crude product was precipitated from dichloromethane solution into hexane solution, yielding pure chromophore I (5.8 g, 11 mmol, 76%).
33. 6) δ [ppm]: 19.3, 40.7, 62.8, 122.8, 127.5, 127.8, 129.9, 131.6, 136.7, 141.2, 144.3, 145.9, 153.0.