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Novel metallophthalocyanines with bulky 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents

Abstract

Novel metallophthalocyanines substituted with four peripheral 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy groups were prepared by Schiff base condensation of 4-aminophenoxy-substituted phthalocyanines with 3,4-bis(benzyloxy)benzaldehyde. The structures were elucidated with elemental analysis, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectrometry, and matrix assisted laser desorption ionization-time of flight spectrometry along with Ultraviolet–Visible spectrophotometry. In the studied concentration range of 1–10 × 10−6 M, no appreciable aggregation of the new species was detected. In tetrahydrofuran, the fluorescent quantum yield ΦF value of the zinc phthalocyanine was lower than the unsubstituted ZnPc (ΦF = 0.25) due to the peripheral [3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents which surely caused fluorescence quenching. The zinc phthalocyanine showed fluorescent quenching by the addition of 1,4-benzoquinone in tetrahydrofuran with obedience to Stern–Volmer kinetics.

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Acknowledgements

Istanbul Technical University Research Fund kindly supported this work. TUBA (Turkish Academy of Sciences) provided partial support to AG.

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Correspondence to Ahmet Gül.

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Sevim, A.M., Yüzeroğlu, M. & Gül, A. Novel metallophthalocyanines with bulky 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents. Monatsh Chem 151, 1059–1068 (2020). https://doi.org/10.1007/s00706-020-02639-w

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