Unsymmetrical phthalocyanines containing azo moiety; Synthesis and photophysical properties

Ebru Özkan Garip, Mukaddes Özçeşmeci, Ramazan Katlrcl, Ibrahim Özçeşmeci, Esin Hamuryudan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


Unsymmetrical metal-free phthalocyanine was synthesized through cyclotetramerization of 4-[2,6-dimethyl-4-(4-tert-butyl-phenylazo)phenoxy]phthalonitrile and 4-(hexylthio)phthalonitrile in the presence of lithium in n-pentanol, then metal-free phthalocyanine was obtained by acidification with acetic acid. Finally, metalation was achieved by refluxing metal-free phthalocyanine in n-pentanol in the presence of zinc (II) salt. The structure of synthesized phthalocyanine derivatives were characterized by using proton nuclear magnetic resonance, mass spectrometry, ultraviolet-visible spectroscopy, and Fourier transform infrared spectroscopy. The HOMO-LUMO energies were computed using density functional theory. The HOMO-LUMO energy difference is 2.28 eV. The calculated results were consistent with the experimental data. In addition, aggregation behaviors and general trends for photophysical properties of these phthalocyanine derivatives were studied in tetrahydrofuran. The emission intensities of these phthalocyanine derivatives were strongly quenched by 1,4-benzoquinone in tetrahydrofuran.

Original languageEnglish
Pages (from-to)1563-1569
Number of pages7
JournalJournal of Porphyrins and Phthalocyanines
Issue number11-12
Publication statusPublished - 1 Nov 2019

Bibliographical note

Publisher Copyright:
© 2019 World Scientific Publishing Company.


This work was supported by the Research Fund of the Istanbul Technical University. The numerical calculations reported in this paper were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).

FundersFunder number
Istanbul Teknik Üniversitesi


    • azo group
    • computational studies
    • photochemistry
    • phthalocyanines
    • synthesis


    Dive into the research topics of 'Unsymmetrical phthalocyanines containing azo moiety; Synthesis and photophysical properties'. Together they form a unique fingerprint.

    Cite this