"Adjacent" substituted phthalocyanines

Synlett

Volumn , Issue 5, 1997, Pages 593-594

  Nolan, K J M ^a   Hu, M ^a   Leznoff, C C ^a  

^a YORK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 53649100595     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3226     Document Type: Article

References (15)

1. Van Lier, J. E. In Photodynamic Therapy of Neoplastic Disease, Vol. 1; Kassel, D., Ed.; CRC: Boca Raton, FL, 1990; p 279.
2. Rosenthal, I. In Phthalocyanines: properties and applications, Vol. 4; Leznoff, C. C.; Lever, A. B. P.; VCH: New York, NY, 1996; p 481.
3. Idelson, E. M. U.S. Patent 4061654, 1977; Chem. Abstr. 1977, 88, 171797m.
4. Young, G.; Onyebuagu, W. J. Org. Chem. 1990, 55, 2155.
5. Kobayashi, N.; Ashida, T.; Osa, T. Chem. Lett. 1992, 2031.
6. Ikeda, Y.; Konami, M.; Hatano, M.; Mochizuki, M. Chem. Lett. 1992, 763.
7. Linssen, T. G.; Hanack, M. Chem. Ber. 1994, 127, 2051.
8. Oliver, S. W.; Smith, T. D.; J. Chem. Soc. Perkin Trans 2 1987, 1587.
9. Hurley, T. J.; Robinson, M. A.; Trotz, S. I. Inorg. Chem. 1967, 6, 389.
10. Terekhov, D. S.; Nolan, K. J. M.; McArthur, C. R.; Leznoff, C. C. J. Org. Chem. 1996, 61, 3034.
11. 4OLi (m/z intensity, %) 295 (M + 1), 88), 289 (78), 280 (51).
12. 2Zn (m/z intensity, %) 638 (M + 2, 96), 637 (M + 1, 90), 636 (M, 100).
13. Konami, H.; Ikeda, Y.; Hatano, M.; Mohizuk, K. J. Mol. Physics 1993, 80, 153.
14. Metz, J.; Schneider, O.; Hanack, M. Inorg. Chem. 1984, 23, 1065.
15. Typical Experimental Procedure: To 20 mL of freshly distilled methanol was added 0.07 g of lithium (10 mmol) and 2.56 g (20 mmol) of 2. The solution was refluxed for 2 h under argon. To 2 mL (2 mmol of 2) of the dark green solution was added 1.84 g (10 mmol) of 4,5-dimethoxyphthalonitrile (3) in 10 mL of 1-octanol. The mixture was heated to 100° C and stirred overnight. Zinc acetate was added to the mixture, which was stirred for another 8 h. The mixture was poured into 50 mL of methanol and water (1:1) to give a blue precipitate which was collected by centrifugation. The residue was passed through a silica gel column to remove some impurities by eluting with THF and hexane (1:1). Further purification was performed by GPC on Bio-beads gel (SX-2) and two main fractions, 15 and 16 were collected in 28 and 22% yields, respectively. Compounds 15 and 16 are both blue solids mp>320° C.