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Aldehyde Substituted Phthalocyanines: Synthesis, Characterization and Investigation of Photophysical and Photochemical Properties

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Abstract

The new free and nickel phthalocyanine derivatives, tetrakis [(2-formylphenoxy)-phthalocyanine (4), tetrakis [(2-formylphenoxy)-phthalocyaninato]nickel(II) (5) have been synthesized via de-protection of tetra acetal-substituted phthalocyanines in acetic acid/FeCl3 system. The starting phthalocyanines, tetrakis [(2-(1,3-dioxolan-2-yl)phenoxy)-phthalocyanine (2) and tetrakis [(2-(1,3-dioxolan-2-yl)phenoxy)-phthalocyaninato]nickel (3), were prepared by the tetramerization of 4-(2-(1,3-dioxolan-2-yl) phenoxy) phthalonitrile (1). The new compounds have been characterized by the combination of FT-IR, 1H NMR, UV–Vis, Mass spectra and elemental analysis. Compound 1 crystallizes in the Orthorhombic, space group Pbca with a = 9.2542 (4) Å, b = 13.3299 (5) Å, c = 23.2333 (11) Å, and Z = 8. Compound 1 is built up from two planar groups (phthalonitrile and phenoxy), with a dihedral angle of 69.693(36)° between them and non-planar dioxolane group. We report a combined experimental and theoretical study on molecule 1, as well. Geometric, spectroscopic and electronic properties of compound 1 has been calculated using B3LYP method and 6–311++G(dp) basis set. Fluorescence spectroscopy was applied to record the photoluminescence spectra of the prepared phthalocyanines and the photophysical and photochemical properties were examined in DMSO.

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Acknowledgments

This work was supported by Ministry of Science, Industry and Technology of Turkey (SANTEZ project no. 0182.STZ.2013-1) and Research Fund of Sakarya University (project no. 2014-02-04 007).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Sciences, Sakarya University, 54187, Sakarya, Turkey

    Pinar Sen & S. Zeki Yildiz

  2. Department of Chemistry, Yildiz Technical University, 34210 Esenler, Istanbul, Turkey

    Ali Erdoğmuş

  3. Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139, Samsun, Turkey

    Necmi Dege

  4. Department of Physics, Faculty of Arts and Sciences, Sakarya University, 54187, Serdivan, Sakarya, Turkey

    Yusuf Atalay

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  1. Pinar Sen
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Sen, P., Yildiz, S.Z., Erdoğmuş, A. et al. Aldehyde Substituted Phthalocyanines: Synthesis, Characterization and Investigation of Photophysical and Photochemical Properties. J Fluoresc 26, 1521–1534 (2016). https://doi.org/10.1007/s10895-016-1852-x

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