Versatile synthetic methods for the engineering of thiophene-substituted Bodipy dyes

Tetrahedron Letters

Volumn 50, Issue 50, 2009, Pages 7008-7013

  Rihn, Sandra ^a   Retailleau, Pascal ^b   Bugsaliewicz, Nicolas ^a   Nicola, Antoinette De ^a   Ziessel, Raymond ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

Bodipys'; Fluorescence; Suzuki coupling; Thiophene; X ray structures

Indexed keywords

BORONIC ACID DERIVATIVE; DYE; THIENYL BORONDIAZADIPYRROMETHENE DYE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ENGINEERING; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; FLUORESCENCE; IRRADIATION; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS; X RAY ANALYSIS;

EID: 70350502275     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.163     Document Type: Article

References (43)

1. Christensen L.P. Rec. Res. Dev. Phytochem. 2 (1998) 227
2. Drehesen G., and Engel J. Sulfur Rep. 3 (1983) 171
3. Mishra A., Ma C.-Q., and Bäuerle P. Chem. Rev. 109 (2009) 1141
4. Roncali J. Chem. Rev. 97 (1997) 173
5. Roncali J. Acc. Chem. Res. 33 (2000) 147
6. Homes B.T., Pennington W.T., and Hanks T.W. Molecules 7 (2002) 447
7. Krömer J., Rios-Carreras I., Fuhrmann G., Musch C., Wunderlin M., Debaerdemaeker T., Mena-Osteritz E., and Bäuerle P. Angew. Chem., Int. Ed. 39 (2000) 3481
8. Mena-Osteritz E., and Bäuerle P. Adv. Mater. 13 (2001) 243
9. Wu R., Schumm J.S., Pearson D.L., and Tour J.M. J. Org. Chem. 61 (1996) 6906
10. Tour J.M. Acc. Chem. Res. 33 (2000) 791
11. Chan H.S.O., and Ng S.C. Prog. Polym. Sci. 23 (1998) 1167
12. Roncali J. J. Mater. Chem. 9 (1999) 1875
13. Martin R.E., and Diederich F. Angew. Chem., Int. Ed. 38 (1999) 1351
14. Pappenfus T.M., Chesterfield R.J., Frisbie C.D., Mann K.R., Casado J., Raff J.D., and Miller L.L. J. Am. Chem. Soc. 124 (2002) 4184 and references cited therein
15. Briehn C.A., Schiedel M.-S., Bonsen E.M., Schumann W., and Bäuerle P. Angew. Chem., Int. Ed. 40 (2001) 4680
16. Facchetti A., Yoon M.-H., Stern C.L., Katz H.E., and Marks T.J. Angew. Chem., Int. Ed. 42 (2003) 3900
17. Yamamoto T., Arai M., Kokubo H., and Sasaki S. Macromolecules 36 (2003) 7986
18. Kraft A., Grimsdale A.C., and Holmes A.B. Angew. Chem., Int. Ed. 37 (1998) 402
19. De Nicola A., Liu Y., Schanze K.S., and Ziessel R. Chem. Commun. (2003) 288
20. De Nicola A., Ringenbach C., and Ziessel R. Tetrahedron Lett. 44 (2003) 183
21. Ziessel R., Ulrich G., and Harriman A. New J. Chem. 31 (2007) 496
22. Ziessel R. Compt. Rendus Acad. Sci. Chim. 10 (2007) 622
23. Ulrich G., Ziessel R., and Harriman A. Angew. Chem., Int. Ed. 47 (2008) 1184
24. Loudet A., and Burgess K. Chem. Rev. 107 (2007) 4891
25. Haughland R.P. Handbook of Fluorescent Probes and Research Products. 9th ed. (2002), Molecular Probes, Eugene, OR pp 36-46
26. Ulrich G., Goeb S., De Nicola A., Retailleau P., and Ziessel R. Synlett 10 (2007) 1517
27. Ulrich G., Goze C., Goeb S., Retailleau P., and Ziessel R. New J. Chem. 30 (2006) 982
28. ABJ = 8.4 Hz, νδAB = 92.9 Hz).
29. Rohand T., Qin W., Boens N., and Dehaen W. Eur. J. Org. Chem. (2006) 4658
30. Li L., Han J., Nguyen B., and Burgess K. J. Org. Chem. 73 (2008) 1963
31. Li L., Nguyen B., and Burgess K. Bioorg. Med. Chem. Lett. 18 (2008) 3112
32. Choi S.-H., Kim K., Jeon J., Meka B., Bucella D., Pang K., Khatua S., Lee J., and Churchill D.G. Inorg. Chem. 47 (2008) 11071
33. Haughland, R. P.; Kang, H. C. U.S. Patent 4774,339, Sep. 27, 1988.
34. Rurack K., Kollmansberger M., and Daub J. New J. Chem. 25 (2001) 289
35. Dost Z., Atilgan S., and Akkaya E.U. Tetrahedron 62 (2006) 8484
36. Yu Y.-H., Descalzo A.B., Shen Z., Röhr H., Liu Q., Wang Y.-W., Spieles M., Li Y.-Z., Rurack K., and You X.-Z. Chem. Asian J. 1-2 (2006) 176
37. Ziessel R., Ulrich G., Harriman A., Alamiry M.A.H., Stewart B., and Retailleau P. Chem. Eur. J. 15 (2009) 1359 and references therein
38. Jestin I., Frère P., Mercier N., Levillain E., Stievenard D., and Roncali J. J. Am. Chem. Soc. 120 (1998) 8150
39. Rousseau T., Cravino A., Roncali J., Bura T., Ulrich G., and Ziessel R. Chem. Commun. (2009) 1673
40. Rousseau T., Cravino A., Roncali J., Bura T., Ulrich G., and Ziessel R. J. Mater. Chem. 19 (2009) 2298
41. Kumaresan D., Thummel R.P., Bura T., Ulrich G., and Ziessel R. Chem. Eur. J. 15 (2009) 6335
42. Qin W., Rohand T., Dehaen W., Clifford D.K., Beljonne D., Van Averbeke M., and Boens N. J. Phys. Chem. A 111 (2007) 8588
43. Olmsted III J. J. Phys. Chem. 83 (1979) 2581