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Synthesis and characterization of O- and S-bridged perfluoroalkylated metal-free and zinc phthalocyanines

İlke Gürol

TUBITAK-Marmara Research Center, Materials Institute, PO Box 21, Gebze 41470, Turkey

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Gülay Gümüş

TUBITAK-Marmara Research Center, Materials Institute, PO Box 21, Gebze 41470, Turkey

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Emel Musluoğlu

TUBITAK-Marmara Research Center, Materials Institute, PO Box 21, Gebze 41470, Turkey

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Yadigar Arslan

TUBITAK-Marmara Research Center, Materials Institute, PO Box 21, Gebze 41470, Turkey

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, and

Vefa Ahsen

TUBITAK-Marmara Research Center, Materials Institute, PO Box 21, Gebze 41470, Turkey

Gebze Institute of Technology, Department of Chemistry, PO Box 141, Gebze 41400, Turkey

Corresponding author, tel: +90 262-605-3106, fax: +90 262-605-3101.

Current address: Gebze Institute of Technology, Department of Chemistry, PO Box 141, Gebze 41400, Turkey.

SPP full member in good standing.

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https://doi.org/10.1142/S1088424613500491Cited by:5 (Source: Crossref)

Abstract

The synthesis of tetra and octa perfluoroalkyl substituted zinc and metal free phthalocyanines (ZnPc and H₂Pc) are reported. The compounds 1–5 have been prepared by nucleophilic substitution of 4-nitrophthalonitrile with 1H,1H,2H,2H-perfluorooctanethiol, 1H,1H,2H,2H-perfluorodecan-1-ol, 1H,1H-perfluorodecan-1-ol, 1H,1H-perfluorotetradecan-1-ol and 1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol, respectively. The compounds 6–8 have been prepared by the reaction of 1H,1H,2H,2H-perfluorodecan-1-ol, 1H,1H-perfluorodecan-1-ol and 1H,1H-perfluoro-3,6,9-trioxatridecan-1-ol with 4,5-dichlororphthalonitrile, respectively. The compound 9 with thia-bridge has been synthesized from 4,5-dichlororphthalonitrile. Zinc and metal free phthalocyanines were obtained from the corresponding phthalonitrile derivatives. All compounds were characterized by using mass, ¹H, ¹⁹F NMR, UV-vis and FT-IR as well as elemental analysis. Tetra substituted Zn(II) phthalocyanines are slightly soluble only in THF (Compound 4a and 7a are insoluble) but metal free phthalocyanines are not soluble. Octa substituted Zn(II) and metal free phthalocyanine are soluble in polar solvents such as THF and DMSO.

Dedicated to Professor Özer Bekaroğlu on the occasion of his 80th birthday

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