Synthesis, photophysicochemical properties and TD-DFT calculations of tetrakis(2-benzoyl-4-chlorophenoxy) phthalocyanines

Yusuf Yilmaz, John Mack, M. Kasim Şener, Mehmet Sönmez, Tebello Nyokong

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The synthesis of metal free, magnesium and zinc tetrakis(2-benzoyl-4- chlorophenoxy) phthalocyanine derivatives (2-4) is described along with their characterization by elemental analysis, IR, UV-visible absorption, and 1H NMR spectroscopy and mass spectrometry. Trends observed in the fluorescence, triplet state, singlet oxygen and photodegradation quantum yields and the triplet state lifetimes are also analyzed. The compounds exhibit high solubility in a wide range of organic solvents and no evidence of aggregation was observed over a wide concentration range. The Zn(II) complex (4) was found to have a very high singlet oxygen quantum yield (ΦΔ = 0.78) in dimethylsulfoxide (DMSO) and a reasonably large triplet state quantum yield (ΦT = 0.82). The photophysical and photochemical properties clearly demonstrate that these compounds could prove useful in singlet oxygen applications such as photodynamic therapy (PDT). DFT and TD-DFT calculations were used to assess the impact of the positional isomerism of the 2-benzoyl-4-chlorophenoxy substituents on the electronic structures and optical spectroscopy.

Original languageEnglish
Pages (from-to)326-335
Number of pages10
JournalJournal of Porphyrins and Phthalocyanines
Volume18
Issue number4
DOIs
Publication statusPublished - 2014 Apr

Keywords

  • TD-DFT calculations
  • phthalocyanine
  • singlet oxygen quantum yields

ASJC Scopus subject areas

  • Chemistry(all)

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