Synthesis of fluorescent rhodamine dyes using an extension of the Heck reaction

Tetrahedron Letters

Volumn 49, Issue 11, 2008, Pages 1860-1864

  David, Emilie ^a   Lejeune, Johan ^a   Pellet Rostaing, Stéphane ^a   Schulz, Jürgen ^a   Lemaire, Marc ^a   Chauvin, Jérome ^b   Deronzier, Alain ^b  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

Benzo b thiophene; Fluorescent dyes; Heck type coupling; Indole; Pictet Spengler reaction; Rhodamine

Indexed keywords

BENZOTHIOPHENE; DIMETHYL SULFOXIDE; FLUORESCENT DYE; INDOLE; METHANOL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODAMINE;

ARTICLE; ARYLATION; CHEMICAL STRUCTURE; DEMETHYLATION; FLAME PHOTOMETRY; FLUORESCENCE; HECK REACTION; QUANTUM YIELD; SYNTHESIS;

EID: 39149121460     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.021     Document Type: Article

References (21)

1. Sauer M., Han K.T., Mueller R., Nord S., Schulz A., Seeger S., Wolfrum J., Arden-Jacob J., Deltau G., Marx N.J., Zander C., and Drexhage K.H. J. Fluoresc. 5 (1995) 247-261
2. Herrmann, R.; Josel, H.-P.; Dextrage, K.-H.; Arden-Jacob, J. US Patent 5,750,409, 1998.
3. Benson, S. C.; Lam, J. Y. L.; Upadhya, K. G.; Radel, P. A.; Zhen, W.; Menchen, S. M. US Patent 5,936,087, 2000
4. Menchen, S. M.; Benson, S. C.; Lam, J. Y. L.; Zhen, W.; Sun, D.; Rosenblum, B. B.; Khan, S. H.; Taing, M. US Patent 2002,044,416, 2002.
5. Diwu, Z.; Liu, J.; Gee, K. U.S. Patent 2004,147,747, 2004.
6. Liu J., Diwu Z., Leung W.-Y., Lu Y., Patch B., and Haugland R.P. Tetrahedron Lett. 44 (2003) 4355-4359
7. Fournier Dit Chabert J., Joucla L., David E., and Lemaire M. Tetrahedron 60 (2004) 3221-3230
8. David E., Rangheard C., Pellet-Rostaing S., and Lemaire M. Synlett (2006) 2016-2020
9. David E., Pellet-Rostaing S., and Lemaire M. Tetrahedron 63 (2007) 8999-9006
10. Lane B.S., and Sames D. Org. Lett. 6 (2004) 2897-2900
11. +).
12. +).
13. +).
14. -).
15. +).
16. 2O: 355.1810. Found: 355.1811.
17. -).
18. Ref = 1 in methanol) was used as the standard.The luminescence lifetime of the complexes was performed after irradiation at λ = 400 nm obtained by the second harmonic of a Titanium: Sapphire laser (picosecond Tsunami laser spectra physics 3950-M1BB) at a 8MHZ repetition rate. The Fluotime 200 from AMS technologies is used for decay acquisition. It consists of a GaAs microchannel plate photomultiplier tube (Hamamatsu model R3809U-50) followed by a time-correlated single photon counting system from picoquant (PicoHarp300). The ultimated time resolution of the system was closed to 30 ps. These measurements were recorded using the technical support from the chemistry platform 'NanoBio campus' in Grenoble (France).
19. Karstens B., and Kobs K. J. Phys. Chem. 84 (1980) 1871-1872
20. Selanger K.A., Falnes J., and Sikkeland T. J. Phys. Chem. 81 (1977) 1960-1963
21. Frank A.J., Otvos J.W., and Calvin M. J. Phys. Chem. 83 (1979) 716-722