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The Synthesis, Characterization, Crystal Structure and Photophysical Properties of a New Meso-BODIPY Substituted Phthalonitrile

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Abstract

A new highly fluorescent difluoroboradipyrromethene (BODIPY) dye (4) bearing an phthalonitrile group at meso-position of the chromophoric core has been synthesized starting from 4-(4-meso-dipyrromethene-phenoxy)phthalonitrile (3) which was prepared by the oxidation of 4-(2-meso-dipyrromethane-phenoxy)phthalonitrile (2). The structural, electronic and photophysical properties of the prepared dye molecule were investigated. The final product exhibit noticeable spectroscopic properties which were examined by its absorption and fluorescence spectra. The original compounds prepared in the reaction pathway were characterized by the combination of FT-IR, 1H and 13C NMR, UV–vis and MS spectral data. It has been calculated; molecular structure, vibrational frequencies, 1H and 13C NMR chemical shifts and HOMO and LUMO energies of the title compound by using B3LYP method with 6-311++G(dp) basis set, as well. The final product (4) was obtained as single crystal which crystallized in the triclinic space group P-1 with a = 9.0490 (8) Å, b = 10.5555 (9) Å, c = 11.7650 (9) Å, α = 77.024 (6)°, β = 74.437 (6)°, γ = 65.211 (6)° and Z = 2. The crystal structure has intermolecular C—H···F weak hydrogen bonds. The singlet oxygen generation ability of the dye (4) was also investigated in different solvents to determine of using in photodynamic therapy (PDT).

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

    Pinar Sen & S. Zeki Yildiz

  2. Faculty of Arts and Sciences, Department of Chemistry, Yıldız Technical University, 34210, Esenler, Istanbul, Turkey

    Göknur Yaşa Atmaca & Ali Erdoğmuş

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

    Necmi Dege

  4. Fatih Faculty of Education, Primary Science Education Department, Karadeniz Technical University, 61300, Sogutlu, Akcaabat, Turkey

    Hasan Genç

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

    Yusuf Atalay

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  1. Pinar Sen
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Correspondence to S. Zeki Yildiz.

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Sen, P., Atmaca, G.Y., Erdoğmuş, A. et al. The Synthesis, Characterization, Crystal Structure and Photophysical Properties of a New Meso-BODIPY Substituted Phthalonitrile. J Fluoresc 25, 1225–1234 (2015). https://doi.org/10.1007/s10895-015-1609-y

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  • DOI: https://doi.org/10.1007/s10895-015-1609-y

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