The synthesis of unsymmetrical sub-phthalocyanines and their ring enlargement to yield the highly unsymmetrical phthalocyanines is reported.
References
1.
Phthalocyanines, Properties and Applications, ed. LeznoffC. C., and LeverA. B. P., VCH, New York, 1989, 1993, 1996, vols 1–4.
2.
BoyleR. W., and DolphinD., Photochem. Photobiol., 1996, 64, 469; (b) J. E. van Lier, in Photodynamic Therapy of Neoplastic Disease, ed. D. D. Kessel, CRC Press, Boca Raton, FL, 1990, Vol I, pp. 279–291.
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MillerO., and OssokoA., Monatsh. Chem., 1972, 103, 150.
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KobayashiN., KondoR., NakajimaS. C., and OsaT., J. Am. Chem. Soc., 1990, 112, 9040.
(a) KudrevichS. V., GilbertS., and van LierJ. E., J. Org. Chem., 1996, 61, 5706; (b) S. V. Kudrevich, N. Brasseur, C. La Madeleine S. Gilbert and J. E. van Lier, J. Med. Chem., 1997, 40, 3897.
7.
AliH., and van LierJ. E., Tetrahedron Lett., 1997, 38, 1157.
8.
A 2: 1 molar ratio of reactants mainly yielded the trinitro subPc, a 4: 1 ratio gave 20% mono-, 50% di- and 30% trinitro subPc and a ratio of 8: 1 gave tri-tert-Bu subPc along with 20–30% mono- and dinitro subPc.
9.
The product ratios completely changed when the temperature of the reaction mixture was slowly raised from room temperature to 90 °C by placing in an oil bath and slowly heating. Precursors 1 and 2 react differently, depending on the temperature.
10.
KudrevichS. V., AliH., and van LierJ. E., J. Chem. Soc., Perkin Trans. 1, 1994, 2767.
