Metal-free, zinc(II) and lead(II) phthalocyanines functioning with 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate groups: Synthesis and investigation of photophysical and photochemical properties

•The preparation of 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate substituted phthalonitrile.•Synthesis of its corresponding metal free and metallophthalocyanines.•The investigation of photophysical and photochemical properties. In this study, the synthesis and characterization...

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Bibliographic Details
Published in:Synthetic metals 2016-10, Vol.220, p.276-285
Main Authors: Demirbaş, Ümit, Pişkin, Mehmet, Barut, Burak, Bayrak, Rıza, Durmuş, Mahmut, Kantekin, Halit
Format: Article
Language:English
Subjects:
Benzotriazole
Derivatives
Fluorescence
Fourier transforms
Infrared spectroscopy
Nuclear magnetic resonance
Photochemical
Photodynamic therapy
Photophysical
Photosensitizer
Phthalocyanine
Spectroscopy
Synthesis
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Summary:•The preparation of 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate substituted phthalonitrile.•Synthesis of its corresponding metal free and metallophthalocyanines.•The investigation of photophysical and photochemical properties. In this study, the synthesis and characterization of 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate substituted novel phthalonitrile compound and its peripherally substituted zinc(II) lead(II) and metal-free phthalocyanine derivatives were performed for the first time. This novel compounds were characterized by obtained data from general spectroscopic methods such as FT-IR, 1H NMR, 13C NMR and mass. The photophysical and photochemical properties of these phthalocyanines were investigated in N,N-dimethylformamide solutions for determination of their photosensitizing abilities in photocatalytic applications such as photodynamic therapy. The lead(II) phthalocyanine complex did not produce any fluorescent in N,N-dimethylformamide because of the heavy atom effect of bigger lead atom. The fluorescence quantum yields of studied zinc(II) and metal-free phthalocyanines were found to quite higher than unsubstituted zinc(II) phthalocyanine due to substitution of the phthalocyanine skeleton. The influence of substituent and variety of the central metal ions on spectroscopic, photophysical and photochemical properties were also determined and compared.
ISSN:0379-6779
1879-3290
DOI:10.1016/j.synthmet.2016.06.026