Synthesis and characterization of tetraethynylphthalocyanines

Tetrahedron

Volumn 54, Issue 17, 1998, Pages 4397-4404

  Maya, Eva M ^a   Haisch, Peter ^a   Vázquez, Purificación ^a   Torres, Tomás ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

METAL; MONOMER; ORGANIC SOLVENT; PHTHALOCYANINE DERIVATIVE; TETRAMER;

ARTICLE; CHEMICAL ANALYSIS; MASS SPECTROMETRY; MATERIALS; OXIDATION; PHYSICAL CHEMISTRY; POLYMERIZATION; PRIORITY JOURNAL; SOLUBILITY; STEREOISOMERISM; SYNTHESIS;

EID: 0032560142     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00153-7     Document Type: Article

References (29)

1. 1. a) Lefevre, D.; Porteu, F.; Balog, P.; Roulliay, G. Z. and Palacin, S.; Langmuir, 1993, 9, 150-161.
2. b) Lefevre, D. Ph.D. Thesis, L'Universite Paris XI Orsay, 1995.
3. 2. Phthalocyanines: Properties and Applications; Leznoff, C. C. and Lever, A. B. P. Eds.; VCH Publishers: New York, 1989, 1992, 1993, 1996; vols I-IV.
4. 3. 2D polymers based on Pcs have been previously prepared and some of their physical properties studied. See for example: a) Wöhrle, D. and Meyer, G.; Kontakte, 1985, 3, 38-48.
5. b) Djurado, D.; Tadlaqui, S.; Hamwi, A. and Cousseins, J. C.; Synth. Met. 1991, 41-43, 2595-2600.
6. 4. Hanack, M. and Lang, M.; Adv. Mater 1994, 6, 819-833.
7. 5. See for example: a) Hanack, M. and Naarmann, H. DE 40 01 158 (Chem. Abst. 1990, P-208923d).
8. b) Vigh, S.; Lam, H.; Janda, P.; Lever, A. B. P. and Leznoff, C. C.; Can. J. Chem. 1991, 69, 1457-1461.
9. c) Terekhov, D. S.; Nolan, K. J. M.; McArthur, C. R. and Leznoff, C. C.; J. Org. Chem. 1996, 61, 3034-3040.
10. d) Isagao, H.; Terekhov, D. S. and Leznoff, C. C.; J. Porph. Phthalocy. 1997, 1, 135-140.
11. e) Nolan, K. J. M. and Leznoff, C. C.; Synlett. 1997, 593-594.
12. 6. a) Ali, H. and Van Lier, J. E.; Tetrahedron Lett. 1997, 38, 1157-1160.
13. b) Maya, E. M.; Vázquez, P and Torres, T.; Chem. Commun. 1997, 1175-1176.
14. 7. a) Sastre, A.; Torres, T. and Hanack, M.; Tetrahedron Lett. 1995, 36, 8501-8504.
15. b) Sastre, A.; Del Rey, B. and Torres, T.; J. Org. Chem. 1996, 61, 8591-8597.
16. 8. Fernández, F.; Torres, T.; Hauschel, B. and Hanack, M.; Chem. Rev., in press
17. 9. a) Geyer, M.; Plenzig, F.; Rauschnabel, J.; Hanack, M.; Del Rey, B.; Sastre, A. and Torres, T.; Synthesis, 1996, 1139-1151.
18. b) Del Rey, B. and Torres, T.; Tetrahedron Lett. 1997, 38, 5351-5354.
19. c) Cabezón, B.; Rodriguez-Morgade, S. and Torres, T.; J. Org. Chem. 1995, 60, 1872-1874.
20. 10. a) Sastre, A.; Torres, T.; Díaz-Garcia, M.A.; Agulló-López, F.; Dhenaut, C.; Brasselet, S.; Ledoux, I. and Zyss, J.; J. Am. Chem. Soc. 1996, 118, 2746-2747.
21. b) De la Torre, G.; Torres, T. and Agulló-López, F.; Adv. Mat. 1997, 9, 265-269.
22. c) Duro, J.A.; De la Torre, G.; Barberá J.; Serrano, J.L. and Torres, T.; Chem. Mat. 1996, 8, 1061-1066.
23. 11. Marcuccio, S. M.; Svirskaya, P. I.; Greenberg, S.; Lever, A. B. P. and Leznoff, CC.; Can. J. Chem. 1985, 63, 3057-3069.
24. 12. Cleavage of TMS-protecting groups in alkynyl derivatives in the presence of metal salts has been described. See for example: Ito, H.; Arimoto, K.; Sensui, H. and Hosomi, A.; Tetrahedron Lett. 1997, 38, 3977-3980.
25. 13 a) Zhang, X. and Xu H. J. Chem. Soc. Faraday Trans. 1993, 89, 3347-3351.
26. b) Margaron, P.; Grégoire, M. J.; Scasnar, V.; Ali, H. and van Lier, J. E.; Photochem. Photobiol. 1996, 63, 217-223.
27. 14. Nishino, N.; Wagner, R. W. and Lindsey, J. S.; J. Org. Chem. 1996, 61, 7534-7544.
28. 15. Wagner, R. W.; Johnson, T. E.; Li, F. and Lindsey, J. S.; J. Org. Chem. 1995, 60, 5266-5273.
29. 5a describes the preparation of tetraethynylphthalocyanine from tetravinylphthalocyanine by successive bromination-dehydrobromination reactions. However, no conclusive data about the structure of this compound were given.