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Synthesis and electronic absorption studies of novel (trifluoromethyl)phenoxy-substituted phthalocyanines

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Abstract

The reaction of 4-[4-(trifluoromethyl)phenoxy]phenol with 4-nitrophthalonitrile in the presence of K2CO3 leads to formation of 4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]phthalonitrile. Tetrakis[4-[4-(trifluoromethyl)phenoxy]phenoxy]-substituted metal-free phthalocyanine was achieved by tetramerization of the phthalonitrile in 2-(dimethylamino)ethanol, whereas metallophthalocyanines were prepared in the presence of zinc, cobalt, or copper salts. These compounds show high solubility in weakly and medium polar solvents, in strongly polar solvents (dimethylformamide, dimethylsulfoxide), and in aromatic hydrocarbons (toluene, benzene). The new phthalocyanines were characterized by elemental analyses, 1H nuclear magnetic resonance (NMR), 13C NMR, 19F NMR, ultraviolet-visible (UV-Vis), Fourier-transform infrared (FT-IR), and mass spectroscopic methods.

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Acknowledgment

This work was supported by the Research Fund of the Technical University of Istanbul and TUBİTAK TBAG:108T448.

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Authors and Affiliations

  1. Department of Chemistry, Istanbul Technical University, Maslak, Istanbul, 34469, Turkey

    Ayfer Kalkan Burat, Zeliha Pınar Öz & Zehra Altuntaş Bayır

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  1. Ayfer Kalkan Burat
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  2. Zeliha Pınar Öz
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  3. Zehra Altuntaş Bayır
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Correspondence to Zehra Altuntaş Bayır.

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Burat, A.K., Öz, Z.P. & Bayır, Z.A. Synthesis and electronic absorption studies of novel (trifluoromethyl)phenoxy-substituted phthalocyanines. Monatsh Chem 143, 437–442 (2012). https://doi.org/10.1007/s00706-011-0614-3

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  • DOI: https://doi.org/10.1007/s00706-011-0614-3

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