Meta-Substituted triphenylamines as new dyes displaying exceptionally large Stokes shifts

Tetrahedron Letters

Volumn 51, Issue 33, 2010, Pages 4429-4432

  Bordeau, Guillaume ^a   Lartia, Rémy ^a   Teulade Fichou, Marie Paule ^a  

^a CNRS   (France)

Author keywords

Fluorescence; Stokes shift; Triphenylamines

Indexed keywords

DYE; TRIPHENYLAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ISOMERIZATION; SUBSTITUTION REACTION; SYNTHESIS; WITTIG REACTION;

EID: 77955416275     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.082     Document Type: Article

References (32)

1. X. Peng, F. Song, E. Lu, Y. Wang, W. Zhou, J. Fan, and Y. Gao J. Am. Chem. Soc. 127 2005 4170 4171
2. R. Ziessel, G. Ulrich, and A. Harriman New J. Chem. 31 2007 496 501
3. Y. Zhou, Y. Xiao, S. Chi, and X. Qian Org. Lett. 10 2008 633 636
4. E. Barni, G. Viscardi, C. D'Ambrosio, H. Leutz, D. Puertolas, S. Tailhardat, P. Destruel, P. Jolinat, and H. Gusten Appl. Spectrosc. 51 1997 1193 1199
5. C. D'Ambrosio, H. Leutz, M. Taufer, and H. Güsten Appl. Spectrosc. 45 1991 484 490
6. M.S. Shchepinov, and V.A. Korshun Nucleosides Nucleotides Nucleic Acids 20 2001 369 374
7. Y. Ohya, K. Yabuki, M. Tokuyama, and T. Ouchi Supramol. Chem. 15 2003 45 54
8. M. Bröring, R. Krüger, S. Link, C. Kleeberg, S. Köhler, X. Xie, B. Ventura, and L. Flamigni Chem. Eur. J. 14 2008 2976 2983
9. C. Allain, F. Schmidt, R. Lartia, G. Bordeau, C. Fiorini-Debuisschert, F. Charra, P. Tauc, and M.-P. Teulade-Fichou ChemBioChem 8 2007 424 433
10. R. Lartia, C. Allain, G. Bordeau, F. Schmidt, C. Fiorini-Debuisschert, F. Charra, and M.P. Teulade-Fichou J. Org. Chem. 73 2008 1732 1744
11. P. Leriche, P. Frre, A. Cravino, O. Alévêque, and J. Roncali J. Org. Chem. 72 2007 8332 8336
12. N. Cocherel, P. Leriche, E. Ripaud, N. Gallego-Planas, P. Frre, and J. Roncali New J. Chem. 33 2009 801 806
13. H.E. Zimmerman, and V.R. Sandel J. Am. Chem. Soc. 85 1963 915 922
14. H.E. Zimmerman J. Am. Chem. Soc. 117 1995 8988 8991
15. H.K. Sinha, and K. Yates J. Am. Chem. Soc. 113 1991 6062 6067
16. J. Dong, K.M. Solntsev, O. Poizat, and L.M. Tolbert J. Am. Chem. Soc. 129 2007 10084 10085
17. F.D. Lewis, and J.S. Yang J. Am. Chem. Soc. 119 1997 3834 3835
18. F.D. Lewis, R.S. Kalgutkar, and J.S. Yang J. Am. Chem. Soc. 121 1999 12045 12053
19. E.M. Crompton, and F.D. Lewis Photochem. Photobiol. Sci. 3 2004 660 668
20. A. Ohshima, M. Ikegami, Y. Shinohara, A. Momotake, and T. Arai Bull. Chem. Soc. Jpn. 80 2007 561 566
21. J.S. Yang, K.L. Liau, C.W. Tu, and C.Y. Hwang J. Phys. Chem. A 109 2005 6450 6456
22. J.S. Yang, S.Y. Chiou, and K.L. Liau J. Am. Chem. Soc. 124 2002 2518 2527
23. X. Huang, and S.L. Buchwald Org. Lett. 3 2001 3417 3419
24. 3, 330.1130; found 330.1127.
25. T. Mallegol, S. Gmouh, M.A. Meziane, M. Blanchard-Desce, and O. Mongin Synthesis 2005 1771 1774
26. G. Lai, X. Bu, J. Santos, and E. Mintz Synlett 1997 1275 1276
27. + (70%).
28. R.B. Mujumdar, L.A. Ernst, S.R. Mujumdar, C.J. Lewis, and A.S. Waggoner Bioconjugate Chem. 4 1993 105 111
29. J. Nygren, N. Svanvik, and M. Kubista Biopolymers 46 1998 39 51
30. R.N. Butlera, A.M. Fahya, A. Foxa, J.C. Stephensa, P. McArdlea, D. Cunninghama, and A.G. Ryderb Tetrahedron Lett. 47 2006 1721 1724
31. M. Nakazono, S. Nanbu, A. Uesaki, R. Kuwano, M. Kashiwabara, and K. Zaitsu Org. Lett. 9 2007 3583 3586
32. D.T. Gryko, J. Piescowska, V. Vetokhina, and D. Wojcik Bull. Chem. Soc. Jpn. 82 2009 1514 1519