Convenient one-pot synthesis of 4-(dialkylaminobenzyl)triphenylphosphonium salts - Application to the synthesis of a fluorescent probe for multiphotonic imaging of biological membranes

Synthesis

Volumn , Issue 10, 2003, Pages 1541-1544

  Porrès, Laurent ^a   Bhatthula, Bharath Kumar Goud ^a   Blanchard Desce, Mireille ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Alkenation; Amines; Conjugation; Fluorescence; Phosphorus; Wittig reactions

Indexed keywords

BIOLOGICAL MEMBRANES; FLUORESCENCE; MEDICAL IMAGING; SALTS; SYNTHESIS (CHEMICAL);

CHEMICAL REAGENTS;

AMINES;

BENZENE DERIVATIVE; FLUORESCENT DYE; PHOSPHONIUM DERIVATIVE; TRIPHENYLPHOSPHONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; FLUORESCENCE; REACTION ANALYSIS; SYNTHESIS; WITTIG REACTION;

EID: 0042744942     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40521     Document Type: Article

References (18)

1. (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
2. (b) Nicolaou, K. C.; Harter, M. W.; Gunzner, J. L.; Nadin, A. Liebigs Ann. Recueil. 1997, 1283.
3. (a) Londergan, T.; Todorova, G.; Zhu, J.; Huang, D. WO 0214305, 2002.
4. (b) Maertens, C.; Zhang, J.-X.; Dubois, P.; Jérôme, R. J. Chem. Soc., Perkin Trans. 2 1996, 713.
5. (c) Marder, S.; Perry, J. US 6267913, 2001.
6. (d) Segura, J. L.; Gomez, R.; Martin, N.; Guldi, D. M. Org. Lett. 2001, 3, 2645.
7. (e) Rumi, M.; Ehrlich, J. E.; Heikal, A. A.; Perry, J. W.; Barlow, S.; Hu, Z.; McCord-Maughon, D.; Parker, T. C.; Röckel, H.; Thayumanavan, S.; Marder, S. R.; Beljonne, D.; Brédas, J.-L. J. Am. Chem. Soc. 2000, 122, 9500.
8. (a) Puccetti, G.; Blanchard-Desce, M.; Ledoux, I.; Lehn, J. M.; Zyss, J. J. Phys. Chem. 1993, 97, 9385.
9. (b) Alain, V.; Redoglia, S.; Blanchard-Desce, M.; Lebus, S.; Lukaszuk, K.; Wortmann, R.; Gubler, U.; Bosshard, C.; Gunter, P. Chem. Phys. 1999, 245, 51.
10. (c) Brunel, J.; Ledoux, I.; Zyss, J.; Blanchard-Desce, M. Chem. Commun. 2001, 923.
11. Banner, B. L.; Weber, G.-F. US 5451600, 1995.
12. 3P·HBr salt, but this procedure requires high thermal activation and a costly reagent: (a) Zhang, J.-X.; Dubois, P.; Jérôme, R. Synth. Commun. 1996, 26, 3091. (b) Samyn, C.; Heylen, M.; Claes, G.; Boutton, C.; Van Beylen, M.; Persoons, A. Eur. Polym. J. 1998, 34, 1069.
13. 3P·HBr salt, but this procedure requires high thermal activation and a costly reagent: (a) Zhang, J.-X.; Dubois, P.; Jérôme, R. Synth. Commun. 1996, 26, 3091. (b) Samyn, C.; Heylen, M.; Claes, G.; Boutton, C.; Van Beylen, M.; Persoons, A. Eur. Polym. J. 1998, 34, 1069.
14. Bredereck, H.; Simchen, G.; Griebenow, W. Chem. Ber. 1973, 106, 3732.
15. Dalton, L. R.; Jen, A. K.-Y.; Londergan, T.; Carlson, W. B.; Phelan, G.; Huang, D.; Casmier, D.; Ewy, T.; Buker, N. WO 0208215, 2002.
16. (a) Ventelon, L.; Charier, S.; Moreaux, L.; Mertz, J.; Blanchard-Desce, M. Angew. Chem. Int. Ed. 2001, 40, 2098.
17. (b) Blanchard-Desce, M. C. R. Physique 2002, 3, 439.
18. (c) Porrès, L.; Mongin, O.; Bhatthula, B. K. G.; Blanchard-Desce, M.; Ventelon, L.; Moreaux, L.; Pons, T.; Mertz, J. Proc. SPIE-Int. Soc. Opt. Eng. 2002, 4812, 24.