New olefinic centred binuclear clamshell type phthalocyanines: Design, synthesis, structural characterisation, the stability and the change in the electron cloud at olefine-based symmetrical diphthalonitrile fragment by the combined application of UV–Vis electronic structure and theoretical methods |
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Authors: | smail Deirmenciolu Rza Bayrak Mustafa Er Kerim Serbest |
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Institution: | a Department of Chemistry, Faculty of Arts and Sciences, Karadeniz Technical University, 61080 Trabzon, Turkey;b Department of Chemistry, Karabük University, 78050 Karabük, Turkey;c Department of Chemistry, Faculty of Arts and Sciences, Rize University, 53050 Rize, Turkey |
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Abstract: | The olefinic centred Schiff base (3) was obtained from the condensation of substituted dialdehyde (1) with 2-amino-4-methylphenol (2) in a 1:2 ratio. The diphthalonitrile derivative (5) was prepared by the reaction of 4-nitrophthalonitrile (4) and compound (3) in dry dimethylformamide/potassium carbonate. The key product (5) was obtained by nucleophilic substitution of an activated nitro group into an aromatic ring. The cyclotetramerization of compound (5) with phthalonitrile (6) in 1:6.15 ratio gave the expected metal-free phthalocyanine of clamshell type (7), and with metal salts of Zn(II), Ni(II), Co(II) and Cu(II) gave metallophthalocyanines of clamshell types (8-11), respectively in dimethylaminoethanol/1,8-diazabycyclo5.4.0]undec-7-ene system. The products were purified by several techniques such as crystallization and preparative thin layer chromatography. The newly prepared compounds were characterised by a combination of elemental analyses, IR, 1H/13C NMR, MS and UV-Vis spectroscopy. |
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Keywords: | Phthalocyanine Metallophthalocyanine Binuclear Clamshell Schiff’ s base Olefinic centred |
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