Phthalocyanines formed from several precursors: synthesis, characterization, and comparative fluorescence and quinone quenching

H. R.Pekbelgin Karaoğlu, H. Yasemin Yenilmez, Makbule B. Koçak*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

We have synthesized a new phthalonitrile with different substituents in 4- and 5-positions (1). Cyclotetramerization of 1 yielded phthalocyanines with cobalt(II) (2), zinc(II) (3), gallium(III)chloride (4), and indium(III)chloride (5) containing diethylamino-phenoxy and hexylsulfanyl substituents on each benzene unit. Elemental analyses, Fourier transform infrared spectra, 1H-nuclear magnetic resonance spectra, mass spectra, and ultraviolet-visible spectra were used for characterization of the phthalocyanines. The aggregation behavior of the zinc phthalocyanine derivative was studied in different concentrations. Also four chloro and four diethyllaminophenoxy substituted zinc phthalocyanine (6) and octa-diethylaminophenoxy substituted zinc phthalocyanine (7) were synthesized. These phthalocyanines (3, 6, and 7) were compared for electronic absorption spectra, fluorescence quantum yields, fluorescent lifetimes, and fluorescence quenching in the presence of benzoquinone. The fluorescence quantum yield gives the efficiency of the fluorescence process. The fluorescence lifetime is an important parameter for practical applications of fluorescence such as fluorescence resonance energy transfer and fluorescence-lifetime imaging microscopy.

Original languageEnglish
Pages (from-to)2340-2357
Number of pages18
JournalJournal of Coordination Chemistry
Volume71
Issue number15
DOIs
Publication statusPublished - 3 Aug 2018

Bibliographical note

Publisher Copyright:
© 2018, © 2018 Informa UK Limited, trading as Taylor & Francis Group.

Keywords

  • aggregation behavior
  • diethylaminophenoxy
  • fluorescence
  • Phthalocyanine
  • quinone

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