Synthesis and characterization of new metal-free and metallophthalocyanines fused α-methylferrocenylmethoxy units

The title compound, β-tetrakis(2,3,4,5,6-pentaphenylbenzene) phthalocyanine, was prepared by cyclotetramerization of 4-(2,3,4,5,6-pentaphenylbenzene)phthalonitrile, in the presence of hydroquinone. The phthalonitrile derivative was synthesized by a Diels−Alder reaction between 4-(phenylethynyl)phthalonitrile and tetracyclone. This methodology was also extended to alkoxy (butyloxy and dodecyloxy)-substituted polyphenylated phthalocyanines and metallophthalocyanines. The polyphenylated design renders the Pcs soluble in common organic solvents. degenerate four-wave mixing studies of the phthalocyanine in dioxane gave χ(3) = 0.52 × 10-10 esu and 〈γ〉 = 6.12 × 10-32 esu, measured at 1064 nm.

Phthalonitrile

Hydroquinone

Derivative (finance)

10.1021/cm9907662

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Citations (23)

Synthesis and properties of 4-(3,5-dichloro-2-hydroxyphenyl) diazenyl metals phthalocyanine

Journal of Science of Teachers' College and University (2013)

Jin Yong-ma

4-(3,5-dichloro-2-hydroxyphenyl) diazenyl phthalonitrile was prepared with 4-nitro phthalonitrile and 2,4-dichloro-phenol as raw materials via reduction,diazotization,coupling reaction,then three 4-(3, 5-dichloro-2-hydroxyphenyl) diazenyl metal phthalocyanines were obtained with substitued phthalonitrile,urea, ammonium molybdate and metal salt in the molten state.The structure and properties of product were charactered by IR spectra,UV-Vis electronic absorption spectra,compared to the spectral properties of the three compounds.The result showed that comparing with non-substitution metal phthalocyanine,different degree of red shift on the Q band with maximum absorption of the substitute phthalocyanine occurred.The order is nickel phthalocyanine,cobalt phthalocyanine and copper phthalocyanine.

Phthalonitrile

Ammonium molybdate

Source

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Novel perfluoroalkyl phthalocyanine metal derivatives: Synthesis and photodynamic activities

Dyes and Pigments (2009)

Tao Qiu Xiaoyong Xu Jianwen Liu Xuhong Qian

Phthalonitrile

Quantum yield

10.1016/j.dyepig.2009.04.007

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Citations (32)

THE PARTICIPATION OF LIGHT IN THE FORMATION OF PHTHALOCYANINE

Chemistry Letters (1976)

Haruhiko Tomoda Eiji Hibiya Takayoshi Nakamura Hiroki Ito Shôjirô SAITÔ

Abstract It was found that roomlight accelerates the formation of phthalocyanine in the reaction of phthalonitrile with sodium alkoxide at elevated temperatures. Moreover, UV irradiation gave phthalocyanine even at room temperature where no formation of phthalocyanine was observed without light.

Phthalonitrile

Alkoxide

10.1246/cl.1976.1003

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Citations (22)

Low-temperature synthesis of phthalocyanine and its metal complexes

Russian Journal of Coordination Chemistry (2006)

Boris I. Kharisov Ubaldo Ortiz Méndez Javier Rivera De la Rosa

Phthalonitrile

Electrosynthesis

Inert

10.1134/s1070328406090016