Method of solubilizing phthalocyanines and metallophthalocyanines

A one-step method of manufacturing soluble phthalocyanines and metallophthalocyanines, like zinc phthalocyanine, by converting a phthalocyanine or a metallophthalocyanine to a trialkylsilyl-substituted derivative is disclosed. The phthalocyanine or metallophthalocyanine is converted to a soluble trialkylsilyl-substituted derivative by interacting the phthalocyanine or metallophthalocyanine with an active metal amide, like lithium 2,2,6,6-tetramethylpiperidide, and a halotrialkylsilane, like chlorotrimethylsilane, to provide a phthalocyanine compound, like phthalocyanine monomers, dimers or polymers, metalated or unmetalated, that are soluble in organic media.

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Claims

1. A phthalocyanine compound exhibiting solubility in organic media and having the formula:

2. The compound of claim 1 wherein x is the numeral 2, the numeral 3, or the numeral 4.

Referenced Cited
U.S. Patent Documents
3759947 September 1973 Pugin et al.
Other references
  • Hanack et al, Chemische Pepichte, 115, 2836-2853 (1982). Hopff et al Helv. Chim. Acta. 51(2) 253-60 Chem. Abstracts vol. 68, 1968. Abstract 106060p. Chen, et al J. Chem. Soc. Perkin Trans. 1, 1989 (5) 1071-3 Chem. Abstracts vol. 111, 1989 Abstract 232758s. Metz et al., "Synthesis and Properties of Substituted (Phthalocyaninato)iron and -cobalt Compounds", Inorg. Chem., 1984, 23, p. 1065. Snow et al., "Molecular Association and Monolayer Formation of Soluble Phthalocyanine Compounds", J. Am. Chem. Soc., 1984, 106, pp. 4706-4711. Koray et al., "Preparation of a Novel Soluble Copper Phthalocyanine with Crown Ether Moieties", J. Chem. Soc., Chem. Commun., 1986, pp. 932-933. Kobayashi et al., "A Copper Phthalocyanine with Four Crown Ether Voids", J. Chem. Soc., Chem. Commun., 1986, pp. 1462-1463. Leznoff et al., "The Synthesis of Mono-and Disubstituted Phthalocyanines Using a Dithioimide", Can. J. Chem., vol. 65, 1987, pp. 1705-1713. Cook et al., "1,4,8,11,15,18,22,25-Octa-alkyl Phthalocyanines: New Discotic Liquid Crystal Materials", J. Chem. Soc., Chem. Commun., 1987, pp. 1086-1088. Krizan and Martin, "In Situ Trapping of Ortho-Lithiated Benzenes Containing Electrophilic Directing Groups.sup.1 ", J. Am. Chem. Soc., 1983, 105, pp. 6155-6157.
Patent History
Patent number: H1695
Type: Grant
Filed: Jun 1, 1990
Date of Patent: Nov 4, 1997
Assignee: The United States of America as represented by the United States Department of Energy (Washington, DC)
Inventors: Jerome W. Rathke (Bolingbrook, IL), Michael J. Chen (Darien, IL), Carol M. Fendrick (Downers Grove, IL)
Primary Examiner: Robert L. Stoll
Assistant Examiner: Joseph D. Anthony
Attorneys: James W. Weinberger, Thomas G. Anderson, William R. Moser
Application Number: 7/531,733